AROMATIC AMINO COMPOUNDS

 

 

The aromatic amino compounds are a class of chemicals derived from aromatic hydrocarbons, such as benzene, toluene, naphthalene, anthracene and diphenyl by the replacement of at least one hydrogen atom by an amino  group. A compound with a free amino group is described as a primary amine. When one of the hydrogen atoms of the  group is replaced by an alkyl or aryl group, the resultant compound is a secondary amine; when both hydrogen atoms are replaced, a tertiary amine results. The hydrocarbon may have one amino group or two, more rarely three. It is thus possible to produce a considerable range of compounds and, in effect, the aromatic amines constitute a large class of chemicals of great technical and commercial value.

 

Aniline is the simplest aromatic amino compound, consisting of one group attached to a benzene ring and its derivatives are most widely used in industry. Other common single-ring compounds include dimethylaniline and diethylaniline, the chloroanilines, nitroanilines, toluidines, the chlorotoluidines, the phenylenediamines and acetanilide. Benzidine, o-tolidine, o-dianisidine, 3,3’-dichlorobenzidine and 4-aminodiphenyl are the most important conjoined ring compounds from the point of view of occupational health. Of compounds with ring structures, the naphthylamines and aminoanthracenes have attracted much attention because of problems of carcinogenicity. Strict precautions necessary for handling carcinogens apply to many members of this family.

 

Azo and diazo dyes

Azo dye is a comprehensive term applied to a group of dyestuffs that carry the azo (-N=N-) group in the molecular structure. The group may be divided into subgroups of monoazo, diazo and triazo dye and further in accordance with the number of the azo group in the molecule. From a toxicological perspective, it is important to take into account that the commercial grade dyestuffs usually contain impurities up to 20% or even higher. The composition and quantity of the impurities are variable depending on several factors such as the purity of the starting materials for the synthesis, the process of synthesis employed and the requirements of the users.

 

Production

Azos dyes are synthesized by diazotization or tetrazotization of aromatic monoamine or aromatic diamine compounds with sodium nitrite in the HCl medium, followed by coupling with dye intermediates such as various aromatic compounds or heterocyclic compounds. When the coupling component carries an amino group, it is possible to produce long-chained polyazo dye by the repetition of diazotization and coupling. The generalized structural formulae for the first three members of the family are:

 

R-N=N-R’

monoazo dye

R-N=N-R’-N=N-R"

diazo dye

R-N=N-R’-N=N-R"-N=N-R’’’

triazo dye

 

Tetrazotization of benzidine and coupling with naphthionic acid yields the very popular dye Congo Red.

 

Uses

Aromatic amino compounds are primarily used as intermediates in the manufacture of dyes and pigments. The largest class of dyestuffs is that of the azo colours, which are made by diazotization, a process by which a primary aromatic amine reacts with nitrous acid in the presence of excess mineral acid to produce a diazo (-N=N-) compound; this compound is subsequently coupled with a phenol or an amine. Another important class of dyestuffs, the triphenylmethane colours, is also manufactured from aromatic amines. In addition to serving as chemical intermediates in the dyestuffs industry, several compounds are employed as dyes or intermediates in the pharmaceutical, fur, hairdressing, textile and photography industries.

 

o-Aminophenol is used for dyeing furs and hair. It is also a developer in the photography industry and an intermediate for pharmaceuticals. p-Aminophenol is used in dyeing textiles, hair, furs and feathers. It finds use in photographic developers, pharmaceuticals, antioxidants and oil additives. 2,4-Diaminoanisole provides an oxidation base for dyeing fur.  o-Toluidine, p-phenylenediamine, diphenylamine and N-phenyl-2-naphthylamine find additional uses as antioxidants in the rubber industry.

 

Diphenylamine is also employed in the pharmaceutical and explosives industries and as a pesticide. N-Phenyl-2-naphthylamine serves as a vulcanization accelerator, a stabilizer for silicone enamels and a lubricant. It is a component of rocket fuels, surgical plaster, tin-electroplating baths and dyes. 2,4-Diaminotoluene and 4,4’-diaminodiphenylmethane are useful intermediates in the manufacture of isocyanates, basic raw materials for the production of polyurethanes.

 

The major use of benzidine is in the manufacture of dyestuffs. It is tetrazotized and coupled with other intermediates to form colours. Its use in the rubber industry has been abandoned. Auramine is used in printing inks and as an antiseptic and a fungicide.

 

o-Phenylenediamine is a photographic developing agent and a hair dye component while p-phenylenediamine is used as a photographic chemical and a dyeing agent for fur and hair. However, p-phenylenediamine has been banned for use as an oxidation dye for hair in some countries. p-Phenylenediamine is also a vulcanization accelerator, a component of gasoline antioxidants. m-Phenylenediamine has numerous functions in the dyestuffs, rubber, textile, hairdressing and photography industries. It finds use in rubber curing agents, ion exchange and decolorizing resins, urethanes, textile fibers, petroleum additives, corrosion inhibitors and hair dyes. It is used as an promoter for adhering tire cords to rubber.

 

Xylidine serves as a gasoline additive as well as raw material in the manufacture of dyes and pharmaceuticals. Melamine is used in moulding compounds, textile and paper treating resins, and in adhesive resins for gluing lumber, plywood and flooring. In addition, it is useful in organic synthesis and in leather tanning. o-Tolidine is a reagent for the detection of gold.

 

Anilines

The anilines are primarily used as intermediates for dyes and pigments. Several compounds are intermediates for pharmaceuticals, herbicides, insecticides and rubber processing chemicals, as well. Aniline itself is widely used in the manufacture of synthetic dyestuffs. It is also used in printing and cloth marking inks and in the manufacture of resins, varnishes, perfumes, shoe blacks, photographic chemicals, explosives, herbicides and fungicides. Aniline is useful in the manufacture of rubber as a vulcanizing agent, as an antioxidant, and as an antiozone agent. A further important function of aniline is in the manufacture of

 

p,p’-methylenebisphenyldiisocyanate (MDI), which is then used to prepare polyurethane resin and spandex fibers and to bond rubber to rayon and nylon.

 

Chloroaniline exists in three isomeric forms: ortho, meta and para, of these only the first and the last are important for manufacturing dyes, drugs and pesticides. p-Nitroaniline is a chemical intermediate for antioxidants, dyes, pigments, gasoline gum inhibitors and pharmaceuticals. It is used in diazotized form to retain fastness of dyes after washing. 4,4’-Methylene-bis(2-chloroaniline), MbOCA, is used as a curing agent with isocyanate-containing polymers for the manufacture of solid abrasion-resistant urethane rubbers and moulded semi-rigid polyurethane foam articles with a hardened skin. These materials are used in an extensive range of products, including wheels, rollers, conveyor pulleys, cable connectors and seals, shoe soles, antivibration mounts and acoustic components. p-Nitroso-N,N,-dimethylaniline and 5-chloro-o-toluidine are used as intermediates in the dyestuffs industry. N,N-Diethylaniline and N,N-dimethylaniline are used in the synthesis of dyestuffs and other intermediates. N,N-Dimethylaniline also serves as a catalytic hardener in certain fibreglass resins.

 

 

Azo compounds

Azo compounds are among the most popular groups of various dyes including direct dyes, acid dyes, basic dyes, naphthol dyes, acid mordant dyes, disperse dyes, etc., and are extensively used in textiles, fabrics, leather goods, paper products, plastics and many other items.

 

Hazards

The manufacture and use in industry of certain aromatic amines may constitute a grave and sometimes unexpected hazard. However, since these hazards have become better known, there has, over recent years, been a tendency to substitute other substances or to take precautions which have reduced the hazard. Discussion has also taken place concerning the possibility of aromatic amines having health effects either when they exist as impurities in a finished product, or when they may be restored as the result of a chemical reaction taking place during the use of a derivative, or-and this is a totally different case-as the result of metabolic degradation within the organism of persons who may be absorbing more complex derivatives.

 

Absorption pathways

Generally speaking, the principal risk of absorption lies in skin contact: the aromatic amines are nearly all lipid-soluble. This particular hazard is all the more important because in industrial practice it is one often not sufficiently appreciated. In addition to skin adsorption, there is also a considerable risk of absorption by inhalation. This may be the result of inhaling the vapours, even though most of these amines are of low volatility at normal temperatures; or it may result from breathing in dust from the solid products. This applies particularly in the case of the amine salts such as sulphates and chlorohydrates, which have a very low volatility and lipid solubility: the occupational hazard from the practical point of view is less but their over-all toxicity is about the same as the corresponding amine, and thus the inhalation of their dust and even skin contact must be considered dangerous.

 

Absorption by way of the digestive tract does represent a potential danger if inadequate eating and sanitary facilities are provided or if workers do not exercise excellent person hygiene practices. Contamination of food and cigarette smoking with dirty hands are two examples of possible ingestion routes.

 

Many of the aromatic amines are flammable and represent a moderate fire hazard. Combustion products can often be highly toxic. The primary health danger of industrial exposure to aniline arises from the ease with which it can be absorbed, either by inhalation or from skin absorption. Because of these absorptive properties, prevention of aniline poisoning requires high standards of industrial and personal hygiene. The most important specific measure for the prevention of spillage or contamination of the work atmosphere with aniline vapour is proper plant design. Ventilation control of the contaminant should be designed as close to the point of generation as possible. Work clothing should be changed daily and facilities for an obligatory bath or shower at the end of the working period should be provided. Any contamination of skin or clothing should be washed off immediately and the individual kept under medical supervision. Both workers and supervisors should be educated to be aware of the nature and extent of the hazard and to carry out the work in a clean, safe manner. Maintenance work should be preceded with sufficient attention to removal of possible sources of contact with the offending chemicals.

 

Since many cases of aniline poisoning result from contamination of the skin or clothing that leads to absorption through the skin, contaminated clothing should be removed and laundered. Even when intoxication results from inhalation, the clothing is likely to be contaminated and should be removed. The entire body surface, including hair and fingernails, should be carefully washed with soap and tepid water. Where methaemoglobinemia is present, appropriate emergency precautions should be taken and the occupational health service must be fully equipped and trained to handle such emergencies. Laundry workers should be provided with adequate precautions to avoid contamination from the aniline compounds.

 

Metabolism

The amines undergo a process of metabolization within the organism. Generally the active agents are the metabolites, some of which induce methaemoglobinaemia, while others are carcinogenic. These metabolites generally take the form of hydroxylamines (R-NHOH), changing to aminophenols  as a form of detoxification; their excretion provides a means of estimating the degree of contamination when the level of exposure has been such that they are detectable.

 

Health effects

Aromatic amines have various pathological effects, and each member of the family does not share the same toxicological properties. While each chemical must be evaluated independently, certain important characteristics are prominently shared by many of them. These include:

 

· cancer of the urinary tract, particularly of the urinary bladder

· danger of acute poisoning, particularly methaemoglobinaemia, which may ultimately have adverse effects on the red cells

· sensitization, notably of the skin, but sometimes respiratory.

 

Toxic effects are also related to chemical characteristics. For example, although an aniline salt has a very similar toxicity to aniline itself, it is not water or lipid soluble and hence not readily absorbed through the skin or by inhalation. Thus, poisoning by aniline salts from industrial exposure are rare.

 

Acute poisoning generally results from the inhibition of haemoglobin function through the formation of methaemoglobin, leading to a condition called methaemoglobinemia, which is discussed more fully in the Blood chapter . Methaemoglobinemia is more often associated with the single-ring aromatic amino compounds. Methaemoglobin is normally present in the blood at a level of about 1 to 2% of the total haemoglobin. Cyanosis at the oral mucosae begins to become apparent at levels of 10 to 15%, though subjective symptoms are normally not experienced until methaemoglobin levels of the order of 30% are reached. With increases above this level, the patient’s skin colour deepens; later, headache, weakness, malaise and anoxia occur, to be succeeded, if absorption continues, by coma, cardiac failure and death. Most cases of acute poisoning react favourably to treatment and the methaemoglobin disappears completely after two to three days. The consumption of alcohol is conducive to and aggravates acute methaemoglobin poisoning. Haemolysis of the red blood cells can be detected after severe poisoning, and is followed by a process of regeneration which is demonstrated by the presence of reticulocytes. The presence of Heinz bodies in the red blood corpuscles may sometimes also be detected.

 

Cancer. The potent carcinogenic effects of the aromatic amines were first discovered in the workplace as a result of the abnormally high incidence of cancer employees in a dye factory. The cancers were described as "dye cancer", but further analysis very soon pointed to their origin being in the raw materials, of which the most important was aniline. They then became known as "aniline cancers". Later, further definition was possible and b-naphthylamine and benzidine were considered to be the “culprit” chemicals. Experimental confirmation of this was long in coming and difficult. Experimental work on many members of this family has found a number to be animal carcinogens. Since insufficient human evidence is available, they have been classified by the International Agency for Research on Cancer (IARC) for the most part as 2B, probable human carcinogens, that is, having sufficient evidence for animal carcinogenicity but insufficient for human carcinogenicity. In some cases, laboratory work has lead to the discovery of human cancer, as in the case of 4-aminodiphenyl, which was first shown to be carcinogenic for animals (in the liver), after which a number of cases of bladder cancer in humans were brought to light.

 

Dermatitis. Because of their alkaline nature, certain amines, particularly the primary ones, constitute a direct risk of dermatitis. Many aromatic amines can cause allergic dermatitis, such as that due to sensitivity to the "para-amines" (p-aminophenol and particularly

 

p-phenylenediamine). Cross-sensitivity is also possible.

 

Respiratory allergy. A number of cases of asthma due to sensitization to p-phenylenediamine, for example, have been reported.

 

Haemorrhagic cystitis can result from heavy exposure to o- and p-toluidine, particularly the chlorine derivatives, of which chloro-5-o-toluidine is the best example. These haematuria appear to be short-lived and the relationship to development of bladder tumours is not established.

 

Liver injuries. Certain diamines, such as toluenediamine and diaminodiphenylmethane, have potent hepatotoxic effects in experimental animals but serious liver damage resulting from industrial exposure has not been a widely reported. In 1966, however, 84 cases of toxic jaundice were reported from eating bread baked from flour contaminated with 4,4’-diaminodiphenylmethane, and cases of toxic hepatitis have also been reported after occupational exposure.

 

Some of the toxicological properties of the aromatic amines are discussed below. Because the members of this chemical family are very numerous, it is not possible to include them all, and there may be others, not included below, which also have toxic properties.

 

Aminophenols

Neither o- nor p-aminophenol isomers, which are crystalline solids of low volatility, are readily absorbed through the skin, although both may act as skin sensitizers and cause contact dermatitis, which appears to be the greatest hazard arising from their use in industry. Although both isomers can cause serious, even life-threatening methaemoglobinaemia, this seldom arises from industrial exposure, since their physical properties are such that neither compound is readily absorbed into the body. p-Aminophenol is the major metabolite of aniline in humans and is excreted in the urine in conjugated form. Bronchial asthma from the ortho isomer has been reported as well.

 

p-Aminodiphenyl is considered a confirmed human carcinogen by IARC. It was the first compound in which the demonstration of carcinogenic activity in experimental animals preceded the first reports of bladder tumours in exposed workers, where it was used as an antioxidant in rubber manufacture. The substance is clearly a potent bladder carcinogen since in one plant with 315 workers, 55 developed tumours as did 11% of 171 workers in another plant manufacturing 4-aminodiphenyl. The tumours appeared 5 to 19 years after initial exposure, and survival ranged in duration from 1.25 to 10 years.

 

Aniline and its derivatives

It has been demonstrated experimentally that aniline vapour can be absorbed via the skin and respiratory tract in approximately equal amounts; however, the rate of absorption of the liquid through the skin is about 1,000 times greater than that of the vapour. The most frequent cause of industrial poisoning is accidental skin contamination, either directly through accidental contact, or indirectly through contact with soiled clothing or footwear. The use of clean and suitable protective clothing and rapid washing in case of accidental contact constitute the best protection. While the US National Institute for Occupational Health and Safety (NIOSH) recommends that aniline be treated as a suspected human carcinogen, IARC has rated it as a Group 3 chemical, meaning insufficient evidence of animal or human carcinogenicity.

 

p-Chloroaniline is a potent methaemoglobin-former and eye irritant. Animal experiments have provided no evidence of carcinogenicity. 4,4’-Methylene bis(2-chloroaniline), or MbOCA, can be absorbed from contact with dust or from fume inhalation, and in industry, skin absorption may also be an important route for uptake. Laboratory studies showed MbOCA or its metabolites may cause genetic damage in a variety of organisms. In, addition, long-term subcutaneous administration in rats resulted in liver and lung tumours. Thus, MbOCA is regarded as an animal carcinogen and a probable human carcinogen.

 

N,N-Diethylaniline and N,N-dimethylaniline are readily absorbed through the skin, but poisoning may also occur through inhalation of vapours. Their hazards may be considered as similar to those of aniline. They are, in particular, potent methaemoglobin-formers.

 

Nitroanilines. Of the three mono-nitroanilines, the most important is p-nitroaniline. All are used as dye intermediates, but the o- and m- isomers only on a small scale. p-Nitroaniline is readily absorbed through the skin and also by inhalation of dust or vapour. It is a powerful methaemoglobin-former, and is alleged, in serious cases, also to bring about haemolysis, or even liver damage. Cases of poisoning and cyanosis have been reported following exposure while cleaning up spills. The chloronitroanilines are also potent methaemoglobin-formers, leading to haemolysis, and are hepatotoxic. They may give rise to dermatitis by sensitization.

 

p-Nitroso-N,N-dimethylaniline possesses both primary irritant and skin sensitizing properties, and it is a common cause of contact dermatitis. Although, occasionally, workers who develop dermatitis may subsequently work with this compound without further trouble, most will suffer a severe recurrence of the skin lesions on re-exposure, and, in general, it is wise to transfer them to other work to avoid further contact.

 

5-Chloro-o-toluidine is readily absorbed through the skin or by inhalation. Although it (and some of its isomers) may cause methaemoglobin formation, the most striking feature is its irritant effect on the urinary tract, resulting in haemorrhagic cystitis characterized by painful haematuria and frequency of micturition. Microscopic haematuria may be present in men exposed to this compound before the cystitis is manifest, but there is no carcinoenic hazard to humans. However, laboratory experiments have cast doubts on the carcinogenicity of other isomers for certain species of animals.

 

Benzidine and derivatives

Benzidine is a confirmed carcinogen, the manufacture and industrial use of which has caused many cases of papilloma and carcinoma of the urinary tract. Among some working populations, more than 20% of all workers have developed the disease. Recent studies indicate that benzidine may raise the rate of cancer at other sites but there is not agreement on this as yet. Benzidine is a crystalline solid with a significant vapour pressure (that is, it forms vapours readily). Penetration through the skin seems to be the most important pathway for the absorption of benzidine, but there is also a hazard from the inhalation of vapour or fine particles. The carcinogenic activity of benzidine has been established by the many reported cases of bladder tumour in exposed workers and by experimental induction in animals. It is a Group1 confirmed human carcinogen according to IARC ratings. The use of benzidine has been discontinued in most places.

 

3,3’-Dichlorobenzidine is a probable human carcinogen (IARC Class 2B). This conclusion is based on a statistically significantly increased tumor incidence in rats, mice and dogs and positive data on its genotoxicity. The structural relationship to benzidine, a known, powerful human bladder carcinogen, lends further weight to the probability that it is a human carcinogen.

 

Diamino-4,4’-diaminodiphenylmethane. The most striking example of the toxicity of this compound was when 84 persons contracted toxic hepatitis as a result of eating bread baked from flour that was contaminated with the substance. Other cases of hepatitis were noted after occupational exposure through skin absorption. It may also give rise to allergic dermatitis. Animal experiments have led to its being a suspected potential carcinogen, but conclusive results have not been obtained. Diaminodiphenylmethane derivatives have been shown to be carcinogens for laboratory animals.

 

Dimethylaminoazobenzene. The metabolism of DAB has been extensively studied and it has been found that it involves reduction and cleavage of the azo group, demethylation, ring hydroxylation, N-hydroxylation, N-acetylation, protein binding and binding of nucleic acids. DAB shows mutagenic properties after activation. It has carcinogenic power by various routes in the rat and mouse (liver carcinoma), and by oral route it causes carcinoma of the bladder in the dog. The only occupational health observation in humans was of contact dermatitis in factory workers handling DAB.

 

Technical measures should prevent any contact with the skin and mucous membranes. Workers exposed to DAB should wear personal protective equipment and their work should be carried out only in restricted areas. Clothing and equipment after use should be placed in an impervious container for decontamination or disposal. Pre-employment and periodical examinations should focus on liver function. In the US, DAB has been included by OSHA among the cancer suspect agents for humans.

 

Diphenylamine. This chemical can be mildly irritating. It appears that under ordinary industrial conditions it offers little hazard, but the potent carcinogen 4-aminodiphenyl may be present as an impurity during the manufacturing process. This may be concentrated to significant proportions in the tars produced at the distillation stage and will constitute a hazard of bladder cancer. While modern manufacturing procedures have enabled the amount of impurities in this compound to be considerably reduced in the commercial product, appropriate prevention must be taken to prevent unnecessary contact.

 

Naphthylamines

The naphthylamines occur in two isomeric forms, -naphthylamine and -naphthylamine.

 

-Naphthylamine is absorbed through the skin and by inhalation. Contact may cause burns to the skin and eyes. Acute poisoning does not arise from its industrial use, but exposure to commercial grades of this compound in the past has resulted in many cases of papilloma and carcinoma of the bladder. It is possible that these tumours were attributable to the substantial

 

-naphthylamine impurity. This matter is not merely of academic interest, as -naphthylamine with greatly reduced levels of b-naphthylamine impurity is now available.

 

-Naphthylamine is a known human bladder carcinogen. Acute poisoning results in methaemoglobinemia or acute haemorrhagic cystitis. Although at one time extensively used as an intermediate in the manufacture of dyestuffs and antioxidants, its manufacture and use has been almost entirely abandoned throughout the world, and it has been condemned as too dangerous to make and handle without prohibitive precautions. It is readily absorbed through the skin and by inhalation. The question of its acute toxic effects does not arise because of its high carcinogenic potency.

 

Phenylenediamines

Various isomeric forms of the phenylenediamines exist but only the m- and p-isomers are of industrial importance. While p-phenylenediamine can act as a methaemoglobin-former in vitro, methaemoglobinaemia arising from industrial exposure is unknown. p-Phenylenediamine is notorious for its sensitizing properties of the skin and respiratory tract. Regular skin contact readily causes contact dermatitis. Acne and leukoderma have also been reported. The former problem of "fur dermatitis" is much less frequent now owing to improvements in the dyeing process having the effect of removing all traces of p-phenylenediamine. Similarly, asthma, at one time common among fur dyers using this substance, is now relatively rare after improvements in the control of airborne dust. Even with controls, a preliminary skin test is useful prior to possible occupational exposure. m-Phenylenediamine is a strong irritant to the skin and causes eye and respiratory irritation. Conclusions drawn from experiments conducted on the phenylenediamines and their derivatives (e.g. N-phenyl or 4- or 2-nitro) relating to their carcinogenic potential are, up to the present time, either insufficient, inconclusive or negative. Chlorine derivatives that have been tested seem to have a carcinogenic potential in animal tests.

 

The carcinogenic potential of commercial mixtures in the past was of great concern because of the presence of b-naphthylamine, which had been found to exist as an impurity in considerable quantities (running into tens or even hundreds of ppm) in some of the older preparations, and by the discovery, in the case of N-phenyl-2-naphthylamine, PBNA, of b-naphthylamine as a metabolic excretion, though in infinitesimal quantities. The experiments point to a carcinogenic potential for the animals tested but do not permit a conclusive judgment to be made, and the degree of significance of the metabolic findings is not yet known. Epidemiological investigations on a large number of persons working under different conditions have not shown any significant increase in the incidence of cancer among workers exposed to these compounds. The amount of b-naphthylamine that is present in the marketed products today is very low-less than 1 ppm and frequently 0.5 ppm. At the present time it is not possible to draw any conclusions as to the true cancer hazard, and for this reason every precaution should be taken, including the elimination of impurities that may be suspect, and technical protective measures in the manufacture and use of these compounds.

 

 

Other compounds

Toluidine exists in three isomeric forms but only the o- and p- isomers are of industrial importance. o-Toluidine and p-toluidine are readily absorbed through the skin, or inhaled as dust, fume or vapour. They are powerful methaemoglobin-formers, and acute poisoning may be accompanied by microscopic or macroscopic haematuria, but they are much less potent as bladder irritants than 5-chloro-o-toluidine. There is sufficient evidence of carcinogenicity in animals to classify o-toluidine and p-toluidine as suspected human carcinogens.

 

Toluenediamines. Among the six isomers of toluenediamine the one most frequently encountered is the 2,4- which accounts for 80% of the intermediate product in the manufacture of toluene diisocyanate, a further 20% being the 2,6- isomer, which is one of the basic substances for the polyurethanes. Attention was drawn to this compound following the experimental discovery of a carcinogenic potential in laboratory animals. Data on humans are not available.

 

Xylidines. Results of animal experiments indicate that they are primarily liver toxins and act secondarily on the blood. However, other experiments have demonstrated that methaemoglobinaemia and Heinz body formation were readily induced in cats, though not in rabbits.

 

Azo Dyes

In general, azo dyes as a group represent a relatively low order of general toxicity. Many of them have an oral  of more than 1 g/kg when tested in rats and mice, and the rodents can be given lifetime laboratory diets containing more than 1 g of the test chemical per kg of diet. A few may cause contact dermatitis but usually with only mild manifestations; in practice, it is rather difficult to determine whether the dye per se or co-existing material is responsible for the observed skin lesion. In contrast, increasing attention has been focused on the carcinogenic potentials of the azo dyes. Although confirmative epidemiological observations are as yet rare, the data from long-term experiments have accumulated to show that some azo dyes are carcinogenic in laboratory animals. The main target organ under such experimental conditions is the liver, followed by the urinary bladder. The intestine is also involved in some cases. It is, however, very problematic to extrapolate these findings to humans.

 

Most of the carcinogenic azo dyes are not direct carcinogens, but pre-carcinogens. That is, they require conversion by in vivo metabolic activation through proximate carcinogens to be ultimate carcinogens. For example, methylaminoazobenzene first undergoes N-hydroxylation and N-demethylation at the amino group, and then sulphate conjugation takes place with the N-hydroxy derivative forming the ultimate carcinogen which is reactive with the nucleic acid.

 

It should be noted that benzidine-derived diazo dyes may be transformed to the highly carcinogenic chemical benzidine by the body’s normal metabolic processes. The body reduces two azo groups in vivo or by the activity of intestinal bacteria, to benizidine. Thus azo dyes should be handled with prudence.

 

Safety and Health Measures

The most important specific measure for the prevention of spillage or contamination of the work atmosphere by these compounds is proper plant design. Ventilation control of the contaminant should be designed as close to the point of generation as possible. Work clothing should be changed daily and facilities for an obligatory bath or shower at the end of the working period should be provided. Any contamination of skin or clothing should be washed off immediately and the individual kept under medical supervision. Both workers and supervisors should be educated to be aware of the nature and extent of the hazard and to carry out the work in a clean, safe manner. Maintenance work should be preceded with sufficient attention to removal of possible sources of contact with the offending chemicals.

 

Aromatic amino compounds tables

 

__________________________________________________________________________

 

Table 104.29.     Chemical identification

 

CHEMICAL

Synonyms

UN code

CAS-NUMBER

CHEMICAL FORMULA

o-ACETOTOLUIDINE

Acetamide, acetyl-o-toluidine;

o-Methylacetanilide;

2-Methylacetanilide;

2’-Methylacetanilide;

N-(2-methylphenyl)acetamide

120-66-1

1-AMINO-2-METHYLANTHRAQUINONE

Acetate fast orange R;

Acetoquinone light orange JL;

1-Amino-2-methyl-9,10-anthracenedione

82-28-0

 

4-AMINODIPHENYL

p-Aminobiphenyl;

4-Aminobiphenyl;

p-Aminodiphenyl;

Biphenylamine

92-67-1

 

 

o-AMINOPHENOL

2-Amino-1-hydroxybenzene;

2-Aminophenol;

o-Hydroxyaniline;

2-Hydroxyanaline;

Nako yellow 3GA

UN2512

95-55-6

 

p-AMINOPHENOL

4-Amino-1-hydroxybenzene;

4-Aminophenol;

Azol;

BASF Ursol P base;

p-Hydroxyaniline;

4-Hydroxyaniline

UN2512

123-30-8

 

ANILINE

Aminobenzene;

Benzenamine;

Phenylamine

UN1547

62-53-3

ANILINE HYDROCHLORIDE

Aniline chloride;

Hydrochloride benzenamide;

Phenylamine hydrochloride

UN1548

142-04-1

o-ANISIDINE

o-Aminoanisole;

2-Aminoanisole;

1-Amino-2-methoxybenzene;

2-Anisidine;

2-Methoxy-1-aminobenzene;

Methoxyphenylamine

90-04-0

 

p-ANISIDINE

p-Aminoanisole;

4-Aminoanisole;

1-Amino-4-methoxybenzene;

4-Anisidine;

4-Methoxy-1-aminobenzene;

Methoxybenzenamine

104-94-9

 

o-ANISIDINE HYDROCHLORIDE

2-Aminoanisole hydrochloride;

o-Aminoanisole hydrochloride ;

o-Anisylamine hydrochloride;

C.I. 37115;

Fast red BB base;

2-Methoxy-1-aminobenzene hydrochloride;

o-Methoxyaniline hydrochloride;

2-Methoxyaniline hydrochloride

134-29-2

 

AURAMINE

Bis(p-dimethylaminophenyl)methyleneimine;

Brilliant oil yellow;

4,4’-Carbonimidoylbis(N,N-Dimethylbenzenamine);

C.I. 41000B;

C.I. basic yellow;

2, 4,4’-dDmethylaminobenzophenonimide;

Glauramine

492-80-8

 

 

BENZIDINE

4,4’-Bianiline;

4,4’-Biphenyldiamine;

C.I. 37225;

C.I. Azoic diazo component 112;

4,4’-Diaminobiphenyl;

4,4’-Diaminodiphenyl;

4,4’-Diphenylenediamine

UN1885

92-87-5

 

 

m-BROMOANILINE

 

591-19-5

 

p-BROMOANILINE

4-Bromobenzenamine;

p-Bromophenylamine

106-40-1

 

2-CHLORO-4-NITROANILINE

1-Amino-2-chloro-4-nitrobenzene;

o-Chloro-p-nitroaniline;

4-Nitro-2-chloroaniline

121-87-9

 

4-CHLORO-o-PHENYLENEDIAMINE

2-Amino-4-chloroaniline;

C.I. 76015;

4-Chloro-1,2-benzenediamine;

4-Chloro-1,2-diaminobenzene;

4-Chloro-1,2-phenylenediamine;

1,2-Diamino -4-chlorobenzene;

3,4-Diaminochlorobenzene;

3,4-Diamino-1-chlorobenzene

95-83-0

 

4-CHLORO-o-TOLUIDINE

2-Amino-5-chlorotoluene;

Azogene fast red TR;

3-Chloro-6-aminotoluene;

5-Chloro-2-aminotoluene;

4-Chloro-2-methylaniline;

4-Chloro-6-methylaniline;

2-Methyl-4-chloroaniline

95-69-2

 

5-CHLORO-o-TOLUIDINE

2H-1-Benzopyran-2-one;

2H-1-Benzopyran, 2-Oxo-;

Benzo--pyrone;

1,2-Benzopyrone;

Cinnamic acid, o-Hydroxy-, d-lactone;

cis-o-Coumarinic acid lactone;

Coumarinic anhydride;

Cumarin;

o-Hydroxycinnamic acid lactone;

o-Hydroxycinnamic lactone;

NCI C07103;

2-Oxo-1,2-benzopyran;

Rattex;

Tonka bean camphor

95-79-4

 

 

o-CHLOROANILINE

1-Amino-2-Chlorobenzene;

2-Chloroaniline;

2-Chlorobenzenamine

95-51-2

 

m-CHLOROANILINE

m-Aminochlorobenzene;

1-Amino-3-Chlorobenzene;

3-Chloroaniline;

3-Chlorobenzenamine

108-42-9

 

p-CHLOROANILINE

1-Amino-4-chlorobenzene;

4-Chlorobenzenamine;

4-Chlorophenylamine

106-47-8

 

p-CRESIDINE

3-Amino-p-cresol methyl ether;

1-Amino-2-methoxy-5-methylbenzene;

3-Amino-4-methoxytoluene;

2-Amino-4-methylanisole;

5-Methyl-o-anisidine;

Azoic red 36

120-71-8

 

N,N’-DI-2-NAPHTHYL-p-PHENYLENEDIAMINE

Aceto DIPP;

Agerite white;

N,N’-Bis(2-naphthyl)-p-phenylenediamine;

Di--naphthyl-p-phenylenediamine;

N,N’-Di-b-naphthyl-p-phenylenediamine;

DNPD;

DNPDA

93-46-9

 

2,4-DIAMINOANISOLE

C.I. 76050;

M-Diaminoanisole 1,3-diamino-4-methoxybenzene;

2,4-Diamino-1-methoxybenzene;

Furro l;

4-Methoxy-1,3-benzenediamine

615-05-4

 

3,3’-DIAMINOBENZIDINE

3,3’,4,4’-Biphenyltetramine ;

3,3’,4,4’-Diphenyltetramine;

3,3’,4,4’-Tetraaminobiphenyl

91-95-2

 

2,4-DIAMINOPHENOL DIHYDROCHLORIDE

Acrol;

amidol;

2,4-Diaminophenol hydrochloride;

Dianol;

NCI-C60026

137-09-7

 

2,4-DIAMINOTOLUENE

3-Amino-p-toluidine;

5-Amino-o-toluidine;

Azogen developer Hh;

Benzofur MT;

C.I. 76035;

1,3-Diamino-4-methylbenzene;

2,4-Siamino-1-methylbenzene

UN1709

95-80-7

 

2,6-DIAMINOTOLUENE

1,3-Benzenediamine, 2-Methyl-;

2,6-toluylenediamine;

2,6-Tolylenediamine

823-40-5

 

N,N-DIBUTYLANILINE

 

613-29-6

 

2,3-DICHLOROANILINE

 

608-27-5

 

2,4-DICHLOROANILINE

Benzenamine, 2,4-Dichloro-

554-00-7

 

2,5-DICHLOROANILINE

 

95-82-9

 

2,6-DICHLOROANILINE

 

608-31-1

 

3,4-DICHLOROANILINE

1-Amino-3,4-Dichlorobenzene;

4,5-Dichloroaniline;

3,4-Dichlorobenzenamine

95-76-1

 

3,3’-DICHLOROBENZIDINE

C.I. 23060;

Curithane C126;

DCB;

4,4’-Diamino-3,3’-dichlorobiphenyl;

Dichlorobenzidine;

3,3’-Dichloro-4,4’-biphenyldiamine

91-94-1

 

3,3’-DICHLOROBENZIDINE

DIHYDROCHLORIDE

(1,1’-Biphenyl)-4,4’-diamine, 3,3’-Dichloro-, dihydrochloride

612-83-9

 

DICYCLOHEXYLAMINONITRITE

N-Cyclohexylcyclohexanamine nitrite;

Dechan;

Diana;

Dicyclohexylammonium nitrite

UN2687

3129-91-7

 

m-DIETHYLAMINOPHENOL

3-(Diethylamino)phenol

91-68-9

 

N,N-DIETHYLANILINE

N,N-Diethylaminobenzene;

Diethylaniline;

N,N-Diethylbenzenamine;

Diethylphenylamine

UN2432

91-66-7

3,3’-DIMETHOXYBENZIDINE

DIHYDROCHLORIDE

o-Dianisidine dihydrochloride;

3,3’-Dimethoxy-4,4’-Diaminobiphenyl dihydrochloride;

3,3’-Dimethoxy-(1,1-biphenyl)-,4’-diamine dihydrochloride

20325-40-0

 

N,N-DIMETHYL-p-TOLUIDINE

Benzenamine, N,N,4-Trimethyl-;

N,N,4-Trimethylaniline;

p-N,N-Trimethylaniline

99-97-8

 

DIMETHYLAMINOAZOBENZENE

p-Dimethylaminoazobenzene;

N,N-Dimethyl-4-aminoazobenzene, Benzeneazodimethylaniline, 4-Dimethylaminoazobenzene,4-Dimethylaminoazobenzol;

DAB

60-11-7

DIMETHYLANILINE

Dimethylaminobenzene;

N,N-Dimethylbenzenamidne;

Dimethylphenylamine

UN2253

121-69-7

2,4-DINITROANILINE

2,4-Dinitraniline;

2,4-Dinitrobenzenamine

97-02-9

 

N,N’-DIPHENYL-p-PHENYLENEDIAMINE

Agerite;

Agerite DPPD;

1,4-Bis(phenylamino)benzene;

Diphenyl-p-phenylenediamine;

DPPD;

Flexamine g;

JZF;

Nonox DPPD

74-31-7

DIPHENYLAMINE

Anilinobenzene;

benzene C.I. 10355;

No scald;

No scald DPA 283;

N-Phenylaniline;

N-Phenylbenzenamine

122-39-4

1,3-DIPHENYLGUANIDINE

Diphenylguanidine;

N,N’-Diphenylguanidine

102-06-7

N-ETHYLANILINE

Anilinoethane;

N-Ethylaminobenzene;

Ethylaniline;

N-Ethylbenzenamine;

Ethylphenylamine

UN2272

103-69-5

 

N-ISOPROPYL-N’-PHENYL-p-

PHENYLENEDIAMINE

Cyzone;

Elastozone 34;

Flexzone 3c;

4-Isopropylaminodiphenylamine;

N-Phenyl-N’-isopropyl-p-phenylenediamine;

N-2-propyl-N’-phenyl-p-phenylenediamine;

Santoflex 36

101-72-4

 

N-ISOPROPYLANILINE

 

768-52-5

 

MELANINE

Aero;

Ammelide;

Cyanuramide;

Cyanuric triamide;

4,6-Triamino-1,3,5-Triazine;

1,3,5-Triazine-2,4,6-triamine

108-78-1

p-METHYLAMINOPHENOL

4-(Methylamino)phenol

150-75-4

 

METHYLANILINE

Anilinomethane;

(Methylamino)benzene;

Methylphenylamine;

Monomethylaniline

UN2294

100-61-8

 

4,4’-METHYLENE-BIS CHLOROANILINE

Bis-amine;

Bis-amine A;

Bisamine S;

Bis(4-amino-3-chlorophenyl)methane;

Bis(3-chloro-4-aminophenyl)methane;

CL-MDA;

Buamine M;

MBOCA;

MOCA

101-14-4

 

4,4’-METHYLENEBIS(2-METHYLANILINE)

Bis(4-amino-3-methylphenyl)methane;

3,3’-Dimethyl-4,4’-diaminodiphenylmethane;

MBOT;

Me-MDA;

4,4’-Methylenebis(2-methylbenzenamine)

838-88-0

 

2,4’-METHYLENEDIANILINE

2’,4-Bis(aminophenyl)methane;

o,p’-Diaminodiphenylmethane;

2,4’-Diaminodiphenylmethane;

2,4’-Diphenylmethanediamine

1208-52-2

 

4,4-METHYLENEDIANILINE

Ancamine tl;

Araldite hardener 972;

Bis(p-aminophenyl)methane;

Bis(4-aminophenyl)methane;

Curithane;

DADPM;

DAPM;

DDM;

Diaminodiphenylmethane;

Dianilinomethane;

4,4’-Diphenylmethanediamine

UN2651

101-77-9

 

MICHLER’S BASE

4,4’-Bis(dimethylamino)diphenylmethane;

Bis(p-dimethylaminophenyl)methane;

Michler’s methane;

Reduced Michler’s ketone;

Tetramethyldiaminodiphenylmethane

101-61-1

 

MICHLER’S KETONE

Bis(p-(N,N-dimethylamino)phenyl)ketone;

Bis(4-(dimethylamino)phenyl)methanone;

4,4’-Bis(dimethylamino)benzophenone;

Tetramethyldiaminobenzophenone

90-94-8

1,5-NAPHTHALENEDIAMINE

1,5-Diaminonaphthalene;

1,5-Naphthylenediamine;

NCI-C03021

2243-62-1

 

a-NAPHTHYLAMINE

1-Naphthylamine;

1-Aminonaphthalene;

C.I. Azoic diazo component 114;

Naphthalidam;

Naphthalidine

UN2077

134-32-7

 

b-NAPHTHYLAMINE

2-Aminonaphthalene;

C.I. 37270;

Fast scarlet base B;

2-Naphthylamine;

2-Naphthalenamine;

6-Naphthylamine

UN1650

91-59-8

o-NITROANILINE

1-Amino-2-nitrobenzene;

2-Nitroaniline

UN1661

88-74-4

m-NITROANILINE

1-Amino-3-nitrobenzene;

Nitranilin;

m-Nitroaniline;

3-Nitroaniline;

3-Nitrobenzenamine

UN1661

99-09-2

 

p-NITROANILINE

p-Aminonitrobenzene;

1-Amino-4-nitrobenzene;

4-Nitroaniline;

4-Nitrobenzenamine

UN1661

100-01-6

  

p-NITROSO-N,N-DIMETHYLANILINE

 

138-89-6

4,4’-OXYDIANILINE

4-Aminophenyl ether;

Diaminodiphenyl ether;

4,4’-Diaminophenyl oxide;

4,4’-Oxybisaniline;

4,4’-Oxybisbenzenamine

101-80-4

   

N-PHENYL-1-NAPHTHYLAMINE

1-Anilinonaphthalene;

Phenylnaphthylamine;

Phenyl--naphthylamine

90-30-2

 

N-PHENYL-b-NAPHTHYLAMINE

Anilinonaphthalene;

2-Anilinonaphthalene;

N-(2-Naphthyl)aniline;

Phenylaminonaphthalene

135-88-6

m-PHENYLENEBIS(METHYLAMINE)

1,3-Bis(aminomethyl)benzene;

MXDA;

m-Xylene-’-Diamine;

m-Xylylenediamine

1477-55-0

o-PHENYLENEDIAMINE

2-Aminoaniline;

o-Benzenediamine;

1,2-Benzenediamine;

C.I. 76010;

C.I. oxidation base 16;

o-Diaminobenzene;

1,2-Diaminobenzene;

o-Phenylenediamine;

1,2-Phenylenediamine

UN1673

95-54-5

 

m-PHENYLENEDIAMINE

m-Aminoaline;

3-Aminoaniline;

m-Benzenediamine;

1,3-Benzenediamine;

C.I. 76025;

Developer 11;

m-Diaminobenzene;

1,3-diaminobenzene;

m-Phenylenediamine;

Metaphenylenediamine;

1,3-Phenylenediamine

UN1673

108-45-2

 

 

p-PHENYLENEDIAMINE

p-Aminoaniline;

4-Aminoaniline;

p-Benzenediamine;

1,4-Benzenediamine;

Benzofur D;

C.I. 76060;

Pelagol D

UN1673

106-50-3

 

 

p-PHENYLENEDIAMINE HYDROCHLORIDE

p-Aminoaniline dihydrochloride;

4-Aminoaniline dihydrochloride;

p-Benzenediamine dihydrochloride;

1,4-Benzenediamine dihydrochloride;

C.I. 76061;

C.I. oxidation base 10A;

p-Diaminobenzene dihydrochloride;

1,4-Diaminobenzene dihydrochloride

624-18-0

 

N-PHENYLETHANOLAMINE

Aniline, N-(2-hydroxyethyl)-;

2-(Phenylamino)ethanol;

N-Phenylethanolamine

122-98-5

o-TOLIDINE

Bianisidine;

(1,1’-Biphenyl)-4,4’-diamine-3,3’-Dimethyl-;

4,4’-bi-o-toluidine;

C.I. 37230;

C.I. Azoic diazo component 113;

4,4’-Diamino-3,3’-dimethylbiphenyl;

4,4’-Diamino-3,3’-dimethyldiphenyl;

3,3’-Dimethylbenzidin

119-93-7

o-TOLUIDINE

1-Amino-2-methylbenzene;

o-aminotoluene;

2-Aminotoluene;

C.I. 37077;

1-Methyl-2-aminobenzene;

o-Methylaniline

UN1708

95-53-4

 

m-TOLUIDINE

3-Amino-1-methylbenzene;

3-Aminophenylmethane;

m-Aminotoluene;

3-Aminotoluene;

m-Methylaniline;

3-Methylaniline

UN1708

108-44-1

 

p-TOLUIDINE

4-Amino-1-methylbenzene;

p-Aminotoluene;

4-Aminotoluene;

C.I. 37107;

C.I. Azoic coupling component 107;

p-Methylaniline;

4-Methylaniline;

p-Methylbenzenamine;

4-Methylbenzenamine

UN1708

106-49-0

 

 

2,4,5-TRIMETHYLANILINE

1-Amino-2,4,5-trimethylbenzene;

1,2,4-Trimethyl-5-Aminobenzene;

2,4,5-Trimethylaniline

137-17-7

 

TRIPHENYLAMINE

N,N-Diphenylaniline;

N,N-Diphenylbenzenamine

603-34-9

 

XYLIDINE

Acid leather brown 2G;

Acid orange 24;

Aminodimethylbenzene;

Dimethylaminobenzene;

Dimethylaniline;

Dimethylphenylamine

UN1711

1300-73-8

2,3-XYLIDINE

2,3-Dimethylaniline;

2,3-Dimethylbenzenamine;

2,3-Dimethylphenylamine;

o-Xylidine;

2,3-Xylylamine

87-59-2

2,4-XYLIDINE

1-Amino-2,4-dimethylbenzene;

4-Amino-1,3-Dimethylbenzene;

4-Amino-3-methyltoluene;

4-Amino-1,3-xylene;

2,4-Dimethylaniline;

2,4-Dimethylbenzenamine

95-68-1

3,4-XYLIDINE

3,4-Dimethylaminobenzene;

3,4-Dimethylaniline;

3,4-Dimethylbenzenamine;

3,4-Dimethylphenylamine;

3,4-Xylylamine

95-64-7

 

 

__________________________________________________________________________

 

Table 104.30. Health hazards

 

CHEMICAL NAME

CAS-NUMBER

ICSC SHORT-TERM EXPOSURE

ICSC LONG-TERM EXPOSURE

ICSC ROUTES OF EXPOSURE AND SYMPTOMS

US NIOSH TARGET ORGANS & ROUTES OF ENTRY

US NIOSH SYMPTOMS

4-AMINODIPHENYL

92-67-1

eyes; bladder

 

Inhalation: dullness, headache

Skin: may be absorbed

Eyes: redness

Bladder; skin (bladder cancer)

Inh; abs; ing; con

Head, dizz; leth, dysp; ataxia, weak; methemo; urinary burning; acute hemorrhagic cystitis; (carc)

o-AMINOPHENOL

95-55-6

blood

skin

Inhalation: blue lips or finger nails, blue skin, cough, dizziness, headache, laboured breathing, unconsciousness, symptoms may be delayed

Eyes: Redness

 

 

ANILINE

62-53-3

eyes; blood; CNS

liver; kidneys; spleen; skin; blood

Inhalation: blue lips or finger nails, blue skin, headache, dizziness, laboured breathing, convulsions, increased heartbeat, vomiting, weakness, unconsciousness

Skin: may be absorbed

Eyes: redness

Blood; CVS; eyes; liver; kidneys; resp sys  (in animals: tumors of the spleen)

Inh; abs; ing; con

Head, weak, dizz; cyan; ataxia; dysp on effort; tacar; irrit eyes; methemo; cirr; (carc)

ANILINE HYDROCHLORIDE

142-04-1

eyes; skin; resp tract; blood

skin; spleen; kidneys; blood

Inhalation: blue lips or finger nails, blue skin, cough, dizziness, headache, nausea, shortness of breath, sore throat, unconsciousness, vomiting, weakness

Skin: may be absorbed, redness

Eyes: redness, pain

Ingestion: abdominal pain

 

 

o-ANISIDINE

90-04-0

blood

blood

Inhalation: blue lips or finger nails, blue skin, dizziness, drowsiness, headache, nausea, vomiting

Skin: may be absorbed

Blood; kidneys; liver; CVS; CNS

Inh; abs; ing; con

Head, dizz; cyan; RBC Heinz bodies; (carc)

p-ANISIDINE

104-94-9

blood

blood

Inhalation: blue lips or finger nails, blue skin, dizziness, drowsiness, headache, laboured breathing, nausea, vomiting

Skin: may be absorbed, blue lips or fingernails, blue skin

Ingestion: blue lips or fingernails, blue skin

Blood; kidneys; liver; CVS; CNS

Inh; abs; ing; con

Head, dizz; cyan; RBC Heinz bodies; (carc)

BENZIDINE

92-87-5

 

 

 

Bladder; kidneys; liver; skin; blood  (liver, kidney and bladder cancer)

Inh; abs; ing; con

Hema; secondary anemia from hemolysis; acute cystitis; acute liver disorders; derm;  painful, irreg urination; (carc)

o-CHLOROANILINE

95-51-2

eyes; skin

skin; liver; kidneys; blood

Inhalation: blue lips or finger nails, blue skin, convulsions, diarrhoea, dizziness, headache, nausea, shortness of breath, vomiting, weakness

Skin: may be absorbed, redness

Eyes: redness, pain

Ingestion: abdominal pain

 

 

m-CHLOROANILINE

108-42-9

eyes; skin; resp tract; liver; kidneys

blood

Inhalation: blue lips or finger nails, blue skin, dizziness, drowsiness, headache, nausea, shortness of breath, unconsciousness

Skin: may be absorbed, redness, burning sensation

Eyes: redness, pain, severe deep burns

Ingestion: abdominal pain,

 

 

p-CHLOROANILINE

106-47-8

eyes; skin; resp tract; blood

skin ; blood; liver; kidneys; spleen ; bone marrow

Inhalation: blue lips or finger nails, blue skin, dizziness, headache, laboured breathing

Skin: may be absorbed, redness

Eyes: redness, pain

Ingestion: nausea

 

 

2,4-DIAMINOTOLUENE

95-80-7

eyes; skin; resp tract; lungs; heart; liver; blood

skin

Inhalation: blue lips or finger nails, blue skin, dizziness, increased heart rate, laboured breathing, nausea, vomiting, convulsions, respiratory depression

Skin: may be absorbed, redness on contact with molten material - skin burns, blisters

Eyes: redness

Ingestion: abdominal pain, blue skin, headache, nausea, vomiting

Eyes, skin, resp sys, blood, CVS, liver, CNS  (in animals: liver, skin & mammary gland tumors)

Inh; abs; ing; con

Irrit eyes, skin, nose, throat; derm; ataxia, tacar, nau, vomit, convuls, resp depres; methemo, cyan, head, ftg, dizz, bluish skin; liver inj; (carc)

2,6-DIAMINOTOLUENE

823-40-5

eyes; skin; resp tract; blood

skin

Inhalation: blue lips or finger nails, blue skin, cough, dizziness, headache, shortness of breath

Skin: redness

Eyes: redness, pain

Ingestion: laboured breathing

 

 

2,3-DICHLOROANILINE

608-27-5

liver; kidneys

skin ; blood

Inhalation: blue lips or finger nails, blue skin, convulsions, diarrhoea, dizziness, headache, shortness of breath, vomiting, weakness

Skin: may be absorbed, redness

Eyes: redness, pain

 

 

2,4-DICHLOROANILINE

554-00-7

liver; kidneys

skin ; blood

Inhalation: blue skin, dizziness, headache, shortness of breath

Skin: may be absorbed, redness, skin burns

Eyes: redness, pain, severe deep burns

Ingestion: abdominal pain, nausea

 

 

2,5-DICHLOROANILINE

95-82-9

liver; kidneys

skin ; blood

Inhalation: blue skin, dizziness, headache, shortness of breath

Skin: may be absorbed, redness, skin burns

Eyes: redness, pain, severe deep burns

Ingestion: abdominal pain, nausea

 

 

2,6-DICHLOROANILINE

608-31-1

liver; kidneys

skin ; blood

Inhalation: blue skin, dizziness, headache, shortness of breath

Skin: may be absorbed, redness

Eyes: redness, pain

 

 

3,4-DICHLOROANILINE

95-76-1

liver; kidneys

skin; blood

Inhalation: blue skin, dizziness, headache, shortness of breath

Skin: may be absorbed, redness, burning sensation

Eyes: redness, pain, severe deep burns

Ingestion: abdominal pain, nausea

 

 

3,3’-DICHLOROBENZIDINE

91-94-1

resp tract

skin; liver

Inhalation: cough, sore throat

Skin: may be absorbed

Bladder; liver; lung ; skin; GI tract  (in animals: liver & bladder cancer)

Inh; abs; ing; con

Skin sens, derm; head, dizz; caustic burns; frequent urination, dysuria; hema; GI upset; upper resp infection; (carc)

DIMETHYLANILINE

121-69-7

blood

skin

Inhalation: abdominal pain, blue skin, dizziness, headache, ringing in the ears, laboured breathing, unconsciousness, vomiting, visual disturbance

Skin: may be absorbed, redness

Eyes: redness, pain

Blood; kidneys;liver; CVS

Inh; abs; ing; con

Anoxia US NIOSH Symptoms; cyan, weak, dizz, ataxia; methemo

DIMETHYLAMINOAZOBENZENE

60-11-7

 

 

 

Skin; resp sys; liver; kidneys; bladder ( in animals: liver & bladder tumors)

Inh; abs; ing; con

Enlarged liver; liver, kidney dysfunc; contact derm; cough, wheez, dysp; bloody sputum; bronchial secretions; frequent urination, hema, dysuria; (carc)

N,N-DIMETHYL-p-TOLUIDINE

99-97-8

blood; brain; kidneys

 

Inhalation: blue lips or finger nails, blue skin, dizziness, headache, shortness of breath, weakness

Skin: may be absorbed

 

 

2,4-DINITROANILINE

97-02-9

eyes; skin; resp tract; blood

blood

Inhalation: blue lips or finger nails, blue skin, cough, dizziness, headache, laboured breathing, nausea, sore throat

Skin: may be absorbed, redness, blue lips or fingernails, blue skin

Eyes: redness, pain

Ingestion: unconsciousness

 

 

DIPHENYLAMINE

122-39-4

eyes; skin; resp tract

kidneys

Inhalation: cough, sore throat

Skin: redness

Eyes: redness

Eyes; skin; resp sys; CVS; blood; bladder; repro sys

Inh; abs; ing; con

Irrit eyes, skin muc memb; eczema; tacar, hypertension; cough, sneez; methemo; incr BP, heart rate; prot, hema, bladder inj; in animals: terato effects

N-ISOPROPYLANILINE

768-52-5

skin; blood; brain; kidneys

skin ; blood

Inhalation: blue lips or finger nails, blue skin, dizziness, headache, laboured breathing

Skin: may be absorbed, blue lips or fingernails, blue skin

Eyes: redness, pain, blurred vision

Ingestion: nausea

Eyes; skin; resp sys; blood; CVS; liver; kidneys

Inh; abs; ing; con

Irrit eyes, skin; head, weak, dizz; cyan; ataxia; dysp on effort; tacar; methemo

N-ISOPROPYL-N’-PHENYL-p-PHENYLENEDIAMINE

101-72-4

eyes; skin

skin

Inhalation: cough, irritant

Skin: redness, irritant

Eyes: redness, irritant

 

 

METHYLANILINE

100-61-8

eyes; skin; resp tract; blood; brain; kidneys

skin; blood

Inhalation: blue lips or finger nails, blue skin, cough, dizziness, headache, laboured breathing, sore throat

Skin: may be absorbed, redness, pain

Eyes: redness, pain, blurred vision

Ingestion: abdominal pain, blue lips or fingernails, blue skin, dizziness, headache, laboured breathing, nausea

Resp sys; liver; kidneys; blood; CNS

Inh; abs; ing; con

Weak, dizz, head; dysp, cyan; methemo; pulm edema; liver, kidney damage

1,5-NAPHTHALENEDIAMINE

2243-62-1

 

skin

Skin: may be absorbed

 

 

-NAPHTHYLAMINE

134-32-7

 

 

 

Bladder; skin  (bladder cancer)

Inh; abs; ing; con

Derm; hemorrhagic cystitis; dysp, ataxia, methemo; hema; dysuria; (carc)

-NAPHTHYLAMINE

91-59-8

 

 

 

Bladder; skin  (bladder cancer)

Inh; abs; ing; con

Derm; hemorrhagic cystitis; dysp; ataxia; methemo, hema; dysuria; (carc)

o-NITROANILINE

88-74-4

blood

 

Inhalation: blue lips or finger nails, blue skin, dizziness, drowsiness, headache, laboured breathing, nausea, shortness of breath, unconsciousness, weakness

Skin: may be absorbed, blue lips or fingernails, blue skin

 

 

m-NITROANILINE

99-09-2

blood

 

Inhalation: blue lips or finger nails, blue skin, dizziness, drowsiness, headache, laboured breathing, nausea, shortness of breath, unconsciousness, weakness

Skin: may be absorbed, blue lips or fingernails, blue skin

 

 

p-NITROANILINE

100-01-6

blood

liver

Inhalation: blue lips or finger nails, blue skin, dizziness, drowsiness, headache, laboured breathing, nausea, shortness of breath, unconsciousness, weakness

Skin: may be absorbed, blue lips or fingernails, blue skin

Resp sys; blood; heart; liver; abs; ing; con

Irrit nose, throat; cyan, ataxia; tacar, tachypnea; dysp; irrity; vomit, diarr; convuls; resp arrest; anemia; methemo; jaundice

N-PHENYL-1-NAPHTHYLAMINE

90-30-2

 

skin

Skin: redness

 

 

p-PHENYLENEDIAMINE

106-50-3

resp tract; blood; kidneys

skin; resp tract

Inhalation: cough, dizziness, headache, laboured breathing

Skin: redness

Eyes: redness, blurred vision, even permanent loss of vision

Ingestion: abdominal pain, blue lips or fingernails, blue skin, vomiting, weakness, convulsions, coma, death

Resp sys ; skin

Inh; abs; ing; con

Irrit pharynx, larynx; bronchial asthma; sens derm

p-PHENYLENEDIAMINE HYDROCHLORIDE

624-18-0

eyes; skin; resp tract; blood; brain; kidneys

skin; resp tract; liver

Inhalation: cough, dizziness, laboured breathing, see ingestion

Skin: redness

Eyes: blurred vision, even permanent loss of vision

Ingestion: abdominal pain, blue lips or fingernails, blue skin, vomiting, weakness, swelling of the face and neck, convulsions, coma, death

 

 

o-TOLIDINE

119-93-7

eyes; skin; resp tract

skin; blood

Inhalation: cough, weak irritant

Skin: may be absorbed

Eyes; resp sys; liver; kidneys; (in animals: liver, bladder & mammary gland tumors)

Inh; abs; ing; con

Irrit eyes, nose; in animals: liver, kidney damage; (carc)

o-TOLUIDINE

95-53-4

 

 

 

Eyes; skin; blood; kidneys; liver; CVS  (in animals: liver, bladder & mammary gland tumors)

Inh; abs; ing; con

Irrit eyes; anoxia, head, cyan; weak, dizz, drow; micro hema, eye burns; derm;  (carc)

XYLIDINE

1300-73-8

eyes; skin; resp tract; blood

kidneys; liver; red blood cells

Inhalation: blue lips or finger nails, blue skin, dizziness, headache, laboured breathing

Skin: may be absorbed

Eyes: redness, pain, blurred vision

Ingestion: blue lips or fingernails, blue skin, dizziness, headache

Resp sys; blood; liver; kidneys; CVS

Inh; abs; ing; con

Anoxia, cyan, methemo; lung, liver, kidney damage

 

__________________________________________________________________________

 

Table 104.31.      Physical and chemical hazards

 

For UN Class: 1.5 = very insensitive substances which have a mass explosion hazard; 2.1 = flammable gas; 2.3 = toxic gas; 3 = flammable liquid; 4.1 = flammable solid; 4.2 = substance liable to spontaneous combustion; 4.3 = substance which in contact with water emits flammable gases; 5.1 = oxidizing substance; 6.1 = toxic; 7 = radioactive; 8 = corrosive substance

 

CHEMICAL NAME

CAS-NUMBER

PHYSICAL

CHEMICAL

UN CLASS/DIV /  SUBSIDIARY RISKS

4-AMINODIPHENYL

92-67-1

 

On combustion, forms toxic gases:   The solution in water is a weak base  Reacts with strong oxidants  Forms salts with acids such as hydrochloric acid, sulfuric acid, etc. 

 

p-AMINOPHENOL

123-30-8

 

 

6.1

o-AMINOPHENOL

95-55-6

 

The substance decomposes on heating producing toxic fumes (nitrogen oxides)  Reacts violently with oxidants causing fire and explosion hazard

6.1

ANILINE

62-53-3

 

The substance decomposes on heating at temperatures above , or on burning producing toxic and corrosive fumes (ammoia and nitrogen oxides) and flammable vapours  The substance is a weak base  Reacts vigorously with strong oxidants, acids, acetic anhydride, chloromelamine monomers, beta-propiolactone and epichlorohydrin causing fire and explosion hazard  Reacts with metals such as sodium, potassium, calcium, producing flammable hydrogen gas  Attacks copper and its alloys

6.1

ANILINE HYDROCHLORIDE

142-04-1

The vapour is heavier than air

On combustion, forms toxic fumes including nitrogen oxides  On contact with hot surfaces or flames this substance decomposes forming toxic and corrosive fumes of aniline and chlorine compounds and nitrosis gases  The substance decomposes on heating or on contact with acids producing toxic fumes including aniline and hydrochloric acid  Reacts violently with oxidants causing fire and explosion hazard

 

o-ANISIDINE

90-04-0

 

The substance decomposes on heating producing toxic fumes (nitrogen oxides)  Reacts with strong oxidants causing fire and explosion hazard  Reacts with acids, acid chlorides, acid anydrides, chloroformates  Attacks some forms of plastics, rubber and coatings

6.1

p-ANISIDINE

104-94-9

 

The substance decomposes on heating producing toxic fumes (nitrogen oxides)  Reacts with strong oxidants causing fire and explosion hazard  Reacts with acids, acid chlorides, acid anydrides, chloroformates

6.1

o-ANISIDINE HYDROCHLORIDE

134-29-2

 

 

6.1

1,4-BENZENEDIAMINE DIHYDROCHLORIDE

624-18-0

Dust explosion possible if in powder or granular form, mixed with air

The substance decomposes on heating producing toxic and corrosive fumes (nitrogen oxides, hydrogen chloride)

 

BENZIDINE

92-87-5

 

 

6.1

2-CHLORO-4-NITROANILINE

121-87-9

 

 

6.1

o-CHLOROANILINE

95-51-2

 

The substance decomposes on burning producing toxic fumes (nitrous oxides, hydrogen chloride)

6.1

m-CHLOROANILINE

108-42-9

 

The substance decomposes on burning producing toxic fumes (nitrous oxides, hydrogen chloride)  The solution in water is a weak base  Reacts violently with oxidants causing fire and explosion hazard

6.1

p-CHLOROANILINE

106-47-8

 

The substance decomposes on heating above and on burning producing toxic and corrosive fumes of nitrogen oxides and hydrogen chloride  Reacts violently with oxidants

6.1

5-CHLORO-o-TOLUIDINE

95-79-4

 

 

6.1

p-CRESIDINE

120-71-8

 

 

8

2,4-DIAMINOTOLUENE

95-80-7

 

On combustion, forms toxic gases and fumes (carbon monoxide and nitrogen oxides)  Reacts with oxidants, acids, acid anhydrides, and acid chlorides

6.1

2,6-DIAMINOTOLUENE

823-40-5

 

On combustion, forms toxic fumes of nitogen oxides

 

2,3-DICHLOROANILINE

608-27-5

 

The substance decomposes on heating producing toxic fumes (nitrous oxides, hydrogen chloride)

6.1

2,4-DICHLOROANILINE

554-00-7

 

The substance decomposes on heating producing toxic fumes (nitrous oxides, hydrogen chloride)

6.1

2,5-DICHLOROANILINE

95-82-9

 

The substance decomposes on heating producing toxic fumes (nitrous oxides, hydrogen chloride)

6.1

2,6-DICHLOROANILINE

608-31-1

 

The substance decomposes on heating producing toxic fumes (nitrous oxides, hydrogen chloride)

6.1

3,4-DICHLOROANILINE

95-76-1

 

The substance decomposes on heating producing toxic fumes (nitrous oxides, hydrogen chloride)

6.1

3,3’-DICHLOROBENZIDINE

91-94-1

 

The substance decomposes on heating producing toxic and corrosive fumes including nitrogen oxides and hydrogen chloride  dergoes usual reactions of benzidine derivates, eg  formation of diazonium salts and acyl and alkyl derivates

 

DICYCLOHEXYLAMINONITRITE

3129-91-7

 

 

4.1

N,N-DIETHYLANILINE

91-66-7

 

 

6.1

N,N-DIMETHYL-p-TOLUIDINE

99-97-8

 

On combustion, forms toxic and corrosive gases (Reacts violently with strong oxidants causing fire and explosion hazard  Reacts with acids, anhydrides and chlorides  Attacks many plastics

 

DIMETHYLANILINE

121-69-7

 

The substance decomposes on heating or on burning producing highly toxic fumes (aniline, nitrogen oxides)  The substance is a weak base  Reacts with oxidants

6.1

2,4-DINITROANILINE

97-02-9

 

May explode on heating, friction or contamination  The substance decomposes on heating producing toxic fumes (nitrogen oxides)  Reacts violently with oxidants  Reacts violently with chlorine and hydrochloric acid evolving gases

6.1

DIPHENYLAMINE

122-39-4

Dust explosion possible if in powder or granular form, mixed with air

On combustion, forms toxic gases of carbon and nitrogen oxides  Reacts with strong oxidants and acids

 

N-ETHYLANILINE

103-69-5

 

 

6.1

N-ISOPROPYL-N’-PHENYL-p-

PHENYLENEDIAMINE

101-72-4

 

On combustion, forms toxic gases (The substance decomposes producing toxic fumes (nitrogen oxides)

 

p-METHYLAMINOPHENOL

150-75-4

 

 

6.1

METHYLANILINE

100-61-8

 

The substance decomposes on heating and on burning producing toxic fumes including aniline, nitrogen oxides  Reacts violently with strong acids and oxidants  Attacks some plastic

6.1

1,5-NAPHTHALENEDIAMINE

2243-62-1

 

The substance decomposes on heating producing toxic fumes (nitrogen oxides)

 

-NAPHTHYLAMINE

134-32-7

 

 

6.1

-NAPHTHYLAMINE

91-59-8

 

 

6.1

o-NITROANILINE

88-74-4

Dust explosion possible if in powder or granular form, mixed with air

On combustion, forms toxic fumes of nitrogen oxides  The substance is a strong oxidant and reacts with combustible and reducing materials  Reacts with organic materials in presence of moisture causing fire hazard

6.1

m-NITROANILINE

99-09-2

Dust explosion possible if in powder or granular form, mixed with air

On combustion, forms toxic fumes of nitrogen oxides  The substance is a strong oxidant and reacts with combustible and reducing materials  Reacts with organic materials in presence of moisture causing fire hazard

6.1

p-NITROANILINE

100-01-6

Dust explosion possible if in powder or granular form, mixed with air

May explode on heating  On combustion, forms toxic fumes of nitrogen oxides  The substance is a strong oxidant and reacts with combustible and reducing materials  Reacts with organic materials in presence of moisture causing fire hazard

6.1

N-PHENYL-1-NAPHTHYLAMINE

90-30-2

 

On combustion, forms toxic fumes (The substance decomposes on heating or on burning producing toxic fumes (nitrogen oxides)

 

o-PHENYLENEDIAMINE

95-54-5

 

 

6.1

m-PHENYLENEDIAMINE

108-45-2

 

 

6.1

p-PHENYLENEDIAMINE

106-50-3

 

The substance decomposes on heating and on burning producing toxic fumes (nitrogen oxides)  The substance is a strong reducing agent and reacts violently with oxidants

6.1

o-TOLIDINE

119-93-7

 

The substance decomposes on heating and on burning producing toxic fumes including nitrogen oxides  The substance is degraded by light

 

o-TOLUIDINE

95-53-4

 

 

6.1

m-TOLUIDINE

108-44-1

 

 

6.1

p-TOLUIDINE

106-49-0

 

 

6.1

XYLIDINE

1300-73-8

 

The substance decomposes on burning producing hazardous oxides of nitrogen  Reacts with strong oxidants  Reacts with hypochlorites forming explosive chloramines

6.1

2,3-XYLIDINE

87-59-2

 

 

6.1

2,4-XYLIDINE

95-68-1

 

 

6.1

3,4-XYLIDINE

95-64-7

 

 

6.1

 

__________________________________________________________________________

 

Table 104.32.    Physical and  chemical properties

 

CHEMICAL NAME

CAS-NUMBER

COLOUR/FORM

BOILING POINT (°C)

MELTING POINT (°C)

MOLECULAR WEIGHT

SOLUBILITY IN WATER

RELATIVE DENSITY (WATER=1)

RELATIVE VAPOUR DENSITY (AIR=1)

VAPOUR PRESSURE/ (KPA)

INFLAM.

Limits

FLASH POINT (°C)

AUTO IGNITION POINT (°C)

o-ACETOLUIDINE

120-66-1

crystals; colourless

296

110

149.2

sl sol

1.168

@ 15 °C

 

 

 

 

 

1-AMINO-2-METHYLANTHRAQUINONE

82-28-0

 

 

205.5

237.3

insol

 

 

 

 

 

 

2-AMINOANTHRAQUINONE

177-79-3

red or orange-brown needles

sublimes

303-6

233.23

insol

 

 

 

 

 

 

4-AMINODIPHENYL

92-67-1

colourless crystals which turn purple on contact with air

302

53

169.2

sl sol

1.160

5.8

@ boiling point

 

 

153 cc

450

o-AMINOPHENOL

95-55-6

crystals, rapidly becoming brown; white rhombic bipyramidal needles from benzene; colourless rhombic needles or plates

153 sublimes

174

109.12

sol

1.328

 

 

 

190

 

p-AMINOPHENOL

123-30-8

orthorhombic plates from water; white plates from water; colourless crystals; white or reddish yellow crystals

284 decomp

188

109.13

sl sol

 

 

 

 

 

 

ANILINE

62-53-3

oily liquid, colourless when pure; colourless with a bluish fluorescence when freshly distilled

184

-6

93.12

sol

1.022

3.22

0.04

1.2 ll

11 ul

70 cc

615

ANILINE HYDROCHLORIDE

142-04-1

crystals

245

198

526.8

v sol

1.22

4.46

 

 

193

 

o-ANISIDINE

90-04-0

pale yellowish liquid; reddish or yellowish coloured oil; colourless to pink liquid

225

5

123.2

sl sol

1.0923

4.25

<0.133

@ 30 °C

 

118 oc

 

p-ANISIDINE

104-94-9

tablets from water, rhombic plates; crystals; fused crystalline mass

246

57

123.15

sol

1.071

@ 57 °C/4 °C

4.28

<13 Pa

 

107

 

AURAMINE

492-80-8

yellow or colourless plates from alcohol

 

136

267.4

insol

 

 

2.5x

 mm Hg

@ 25 °C 

 

 

 

1,4-BENZENEDIAMINE DIHYDROCHLORIDE

624-18-0

crystals

 

 

181.06

sol

 

6.2

 

 

 

 

BENZIDINE

92-87-5

white or slightly-reddish, crystalline powder; needles, grayish, yellow crystalline powder

400

120

184.23

sl sol

1.250

6.36

 

 

 

 

2-CHLORO-4-NITROANILINE

121-87-9

yellow needles from petroleum ether-carbon disulfide, water, 20% acetic acid

 

108

172.57

misc

 

 

 

 

 

 

o-CHLOROANILINE

95-51-2

amber liquid

208.8

-14

127.57

insol

1.2114

@ 22 °C/4 °C

4.41

0.05

 

108

>500

m-CHLOROANILINE

108-42-9

colourless to light amber liquid

230.5

-10

127.57

insol

1.2161

4.4

9 Pa

 

118 cc

>540

p-CHLOROANILINE

106-47-8

orthorhombic crystals from alcohol or petroleum ether; rhombic prisms; colourless crystals

232

72.5

127.6

sol

1.4

4.4

2 Pa

2.2 ll

? ul

120-123

685

4-CHLORO-o-PHENYLENEDIAMINE

95-83-0

 

 

76

142.6

sl sol

 

 

 

 

 

 

5-CHLORO-o-TOLUIDINE

95-79-4

grayish-white solid

237 ( at 722 mm Hg)

26

141.6

 

 

 

 

 

 

 

p-CRESIDINE

120-71-8

white crystals

235

52

137.2

sl sol

 

 

1.02x

 mm Hg

@ 25 °C 

 

 

 

N,N’-DI-2-NAPHTHYL-p-

PHENYLENEDIAMINE

93-46-9

 

 

235

360.43

 

 

 

 

 

 

 

2,4-DIAMINOANISOLE

615-05-4

 

 

67.5

138.16

 

 

 

 

 

 

 

3,3’-DIAMINOBENZIDINE

91-95-2

solid

 

178-180

 

 

 

 

 

 

 

 

4,4’-DIAMINODIPHENYLMETHANE

101-77-9

 

398-399

92.5

198.25

sl sol

 

 

 

 

 

 

2,4-DIAMINOPHENOL

DIHYDROCHLORIDE

137-09-7

grayish-white crystals; needles

 

205

197.08

v sol

 

 

 

 

 

 

2,4-DIAMINOTOLUENE

95-80-7

needles from water or crystals from alcohol; prisms; colourless crystals

292

99

122.2

v sol

 

4.2

0.13

@ 106.5 °C

 

149

 

2,6-DIAMINOTOLUENE

823-40-5

colourless crystals

289

106

122.17

sol

 

 

2.13

@ 150 °C

 

 

 

N,N-DIBUTYLANILINE

613-29-6

amber liquid

267-275

 

 

insol

0.904

 

 

 

110

 

2,3-DICHLOROANILINE

608-27-5

needles from petroleum ether icsc: colourless crystals

252

24

162.02

insol

 

5.6

< 0.01 Pa

@ 25 °C

 

>112 cc

 

2,4-DICHLOROANILINE

554-00-7

prisms from acetone; needles from diluted alcohol or petroleum ether

245

64

162.0

sl sol

1.567

5.6

<1 Pa

@ 25 °C

 

 

 

2,5-DICHLOROANILINE

95-82-9

light brown or amber-coloured crystalline mass; needles from petroleum ether

251

50

162.0

sl sol

1.54

5.6

<1 Pa

@ 25 °C

 

139

>540

2,6-DICHLOROANILINE

608-31-1

crystals

97

39

 

insol

 

5.6

 

 

 

 

3,4-DICHLOROANILINE

95-76-1

needles from petroleum ether; fine, light-tan crystals

272

71-72

162.03

insol

1.36

5.6

2 Pa

2.8

@ 152 °C ll

7.2

@ 179 °C ul

166 oc

269

3,3’-DICHLOROBENZIDINE

91-94-1

needles from alcohol or benzene; gray or purple crystalline solid.

402

132-133

253.13

insol

 

 

6x

 Pa 

 

 

350

DICYCLOHEXYLAMINE NITRITE

3129-91-7

 

 

 

228.32

 

 

 

 

 

 

 

m-DIETHYLAMINOPHENOL

91-68-9

white, crystalline solid

276-280

78

165.23

sol

 

 

 

 

 

 

N,N-DIETHYLANILINE

91-66-7

colourless to yellow liquid; brown oily liquid

216

-38

149.23

sl sol

0.9307

1.0

 

 

 

 

N,N-DIMETHYL-p-TOLUIDINE

99-97-8

liquid

211

 

135.20

insol

0.9366

4.7

0.02

1.2 ll

7 ul

83

 

DIMETHYLAMINOAZOBENZENE

60-11-7

yellow crystalline leaflets

decomp

114-117

225.28

13.6 ppm

 

 

3.3x

mm Hg (est).

 

 

 

DIMETHYLANILINE

121-69-7

oily liquid; pale yellow

194

2.5

121.2

sl sol

0.956

4.17

67 Pa

 

62

371

2,4-DINITROANILINE

97-02-9

yellow needles from diluted acetone, greenish-yellow plates from alcohol.

56.7

188

183.12

insol

1.615 g/ml

@ 14 °C

6.31

5.94x

 mm Hg

@ 25 °C 

 

224 cc

 

N,N’-DIPHENYL-p-PHENYLENEDIAMINE

74-31-7

colourless leaflets from alcohol; commercial grades are greenish-brown; gray powder

220-225

@ 0.5 mm Hg

150-151

260.32

insol

1.20

9.0

 

 

 

 

DIPHENYLAMINE

122-39-4

monoclinic leaflets from diluted alcohol; crystals; solid or liquid, very pale tan-amber to brown

302

53

169.2

insol

1.16

5.82

133 Pa

@ 108 °C

 

153 oc

634

1,3-DIPHENYLGUANIDINE

102-06-7

monoclinic needles; white powder

170 D

150

211.3

sl sol

1.13

 

 

 

 

 

N-ETHYLANILINE

103-69-5

colourless liquid; clear to straw-coloured, yellow-brown oil

204.5

-63.5

121.2

insol

0.9625

4.2

1 mm Hg

@ 38.5 °C

 

 

 

HYDROXYLAMINE

7803-49-8

large white flakes or white needles; colourless liquid

56.5

@ 22 mm Hg

32.05

33.04

v sol

1.2255

@ 0 °C/4 °C

 

 

 

 

 

HYDROXYLAMINE HYDROCHLORIDE

5470-11-1

crystals

 

decomp

 

83 g/100 ml

@ 17 °C

1.7

 

 

 

 

 

HYDROXYLAMINE SULPHATE

10039-54-0

colourless crystals

 

177

 

sol

 

 

 

 

 

 

N-ISOPROPYL-N’-PHENYL-p-

PHENYLENEDIAMINE

101-72-4

dark gray to black flakes

 

72.5

226.3

insol

1.04

@ 25 °C

 

 

 

 

 

N-ISOPROPYLANILINE

768-52-5

yellowish liquid

203

 

135.2

insol

0.9526 25 °C

 

 

 

878

 

MELAMINE

108-78-1

monoclinic prisms; colourless; white

 

<250

126.13

sl sol

1.573

@ 14 °C

4.34

50 mm Hg

@ 315 °C

 

 

 

p-METHYLAMINOPHENOL

150-75-4

colourless needles

 

87

123.17

sol

 

 

5.77x

 mm Hg

@ 25 °C 

 

 

 

METHYLANILINE

100-61-8

colourless to reddish-brown oily liquid

196

-57

107.15

insol

0.989

3.70

133 Pa

@ 36 °C

 

795 cc

 

4,4’-METHYLENE BIS(2-CHLOROANILINE)

101-14-4

tan coloured pellets

 

110

267.15

insol

1.44

 

1.3x

 torr

@ 60 °C 

 

 

 

MICHLER’S BASE

101-61-1

lustrous leaflets; yellowish leaflets or glistening plates

390

91.5

254.36

insol

 

 

 

 

 

 

MICHLER’S KETONE

90-94-8

white to greenish leaflets; leaf in alcohol, needles in benzene

>360 decomp

172

268.35

insol

 

 

 

 

 

 

1,5-NAPHTHALENEDIAMINE

2243-62-1

colourless crystals

sublimes

190

158.2

sl sol

1.4

 

 

 

 

 

-NAPHTHYLAMINE

134-32-7

needles from diluted ethanol and ether; yellow rhombic needles; white crystals; needles, become red on exposure to air or a reddish, crystalline mass

300.8

50

143.18

sl sol

1.0228

4.93

1 mm Hg

@ 104.3 °C

 

157 cc

 

-NAPHTHYLAMINE

91-59-8

colourless crystals which darken in air to a reddish-purple colour

306

113

143.18

sol

1.061

@ 98 °C/4 °C

4.95

1 mm Hg

@108.0 °C

 

157

 

o-NITROANILINE

88-74-4

yellow-orange crystals from boiling water; plates or needles; orange solid

284

71

138.1

sl sol

0.9015

@ 25 °C/4 °C

 

133 Pa

@ 104 °C

 

168

521

m-NITROANILINE

99-09-2

yellow crystals from water; yellow rhombic needles

306

114

138.1

sl sol

0.9011

@ 25 °C/4 °C

 

0.005 Pa

@ 25 °C

 

 

 

p-NITROANILINE

100-01-6

yellow monoclinic needles; bright yellow powder

332

146

138.12

1 g/1250 ml

1.424

4.77

0.2 Pa

 

199

180

4,4’-OXYDIANILINE

101-80-4

colourless crystals

>300

186-187

200.2

insol

 

 

3.07x

 mm Hg

@ 25°

 

 

 

N-PHENYL-1-NAPHTHYLAMINE

90-30-2

powder

335

62

219.27

sl sol

1.2

 

 

 

 

 

N-PHENYL--NAPHTYLAMINE

135-88-6

needles from methanol; white to yellowish crystals; gray to tan flakes or powder

395.5

108

219.29

insol

1.24

 

 

 

 

 

m-PHENYLENEBIS(METHYLAMINE)

1477-55-0

colourless liquid

247

 

136.2

v sol

1.052

 

0.03 mm Hg

@ 25 °C

 

 

 

o-PHENYLENEDIAMINE

95-54-5

brownish-yellow leaf from water; plates from chloroform

257

103

108.14

sol

 

 

 

1.5 ll

? ul

 

 

m-PHENYLENEDIAMINE

108-45-2

white crystals becoming red on exposure to air; colourless needles; rhombic crystals from alcohol; colourless rhombic needles

285

63.5

108.14

v sol

1.139

1.1309

@ 5°C

1 mm Hg

@ 99.8 °C

 

 

 

p-PHENYLENEDIAMINE

106-50-3

white to slightly red crystals; white plates from benzene, ether

267

146

108.14

sl sol

1.14

3.72

<1 mm

@ 21 °C

1.5 ll

? ul

156

 

N-PHENYLETHANOLAMINE

122-98-5

 

286

 

137.17

sl sol

1.0945

 

 

 

 

 

o-TOLIDINE

119-93-7

white to reddish crystals or crystal powder

300

131.5

212.28

sl sol

1

 

 

 

 

 

o-TOLUIDINE

95-53-4

light yellow liquid becoming reddish brown on exposure to air and light; colourless liquid

200.2

-14.7-16.3

107.15

sl sol

1.008

3.69

0.32 torr

 

 

 

m-TOLUIDINE

108-44-1

colourless liquid

203

-30.4

107.15

sl sol

0.9889

3.90

1 mm Hg

@ 41 °C

 

861

 

p-TOLUIDINE

106-49-0

lustrous plates or leaflets; white solid; colourless leaflets

200.5

44

107.15

sl sol

1.046

3.9

0.34 torr

 

 

 

2,4,5-TRIMETHYLANILINE

137-17-7

white crystals; needles obtained from water as solvent

235

68

135.2

insol

0.957

@ 25 °C

 

 

 

 

 

TRIPHENYLAMINE

603-34-9

monoclinic crystals from methanol, ethyl acetate, benzene; colourless

365

127

245.3

insol

0.774

@ 0 °C/0 °C

 

 

 

 

 

XYLIDINE

1300-73-8

exists in 6 isomeric forms varying from a light yellow to a brown liquid; all isomers except ortho-4-xylidine are liquids above 27 °C

213-226

-15 - 51

121.18

sl sol

0.97-0.99

4.17

20 Pa

1 ll

7 ul

91

405

2,3-XYLIDINE

87-59-2

liquid

221.5

< -15

121.2

sl sol

0.9931

 

0.1 mm Hg

@ 25 °C

1.0 ll

? ul

97 cc

 

2,4-XYLIDINE

95-68-1

colourless liquid

214

-14.3

121.2

sl sol

0.9723

 

1 mm Hg

@ 52.6 °C

 

 

 

3,4-XYLIDINE

95-64-7

plates of prisms from petroleum ether

226

51

121.2

sl sol

1.076

@ 18 °C