Diazoaminobenzene

Description

Diazoaminobenzene (DAAB) is an aromatic amine that is a suspected carcinogen. It is harmful if inhaled, ingested, or absorbed through the skin. It causes skin irritation and severe irritation to eyes. DAAB can be made by diazotizing aniline dissolved in hydrochloric acid with sodium nitrite and then adding a concentrated solution of sodium acetate. DAAB is listed in the US Environmental Protection Agency’s Toxic Substances Control Act Inventory. DAAB has three major use areas: intermediate, complexing agent, and polymer additive. Use as an intermediate is reported in several industry sectors, including organic synthesis, dye manufacture, and agrochemical manufacture (insecticides). DAAB is also a versatile metal complexing agent. A series of metabolism studies in rodents and human liver slices, electron spin resonance spectroscopy studies, short-term dermal toxicity studies in rodents, and acute bone marrow micronucleus studies in mice demonstrated that DAAB is metabolized and shares similar genotoxic and toxicological properties to the known human carcinogen, benzene, and the known rodent carcinogen, aniline.

Chemical Properties

ochre powder

Uses

Diazoaminobenzene is used as a chemical intermediate, complexing agent, and polymer additive (Mathews and De Costa 1999). It has uses associated with organic synthesis and dye and insecticide manufacture (Lewis 1997), and it is an effective dopant for laser ablation (micro-machining) of polymethylmethacrylate (Bolle et al. 1990). Diazoaminobenzene has been identified as a low-level contaminant in the dyes D&C red no. 33, FD&C yellow no. 5 (tartrazine), and FD&C yellow no. 6; all three are permitted for use in drugs and cosmetics, and the latter two are permitted in food (FDA 2010).

Uses

1,3-Diphenyltriazene can be used to prepare degradable polyester foam material.

Uses

DAAB is used as a chemical intermediate, a complexing agent, and as a polymer additive. DAAB has been used to promote adhesion of natural rubber to steel tire cords. It has also been used as a blowing agent in the production of a foamed polymeric material. In addition, DAAB is used in the manufacture of dyes and insecticides. DAAB is also an impurity in certain color additives used in cosmetics, food products, and pharmaceuticals. In addition, it has been reported to show semiconducting properties and to be useful as a dopant for poly methylmethacrylate in semiconductor manufacture.

General Description

Orange solid.

Air & Water Reactions

Dust can be explosive when suspended in air at specific concentrations. Insoluble in water.

Reactivity Profile

1,3-DIPHENYLTRIAZENE is an azo compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides. 1,3-DIPHENYLTRIAZENE explodes when heated to above 150°C. A mixture of the triazine and acetic anhydride exploded violently upon warming, Ber., 1891, 24, 4160.

Health Hazard

ACUTE/CHRONIC HAZARDS: 1,3-DIPHENYLTRIAZENE may explode if subjected to severe shock or heat.

Fire Hazard

Flash point data for 1,3-DIPHENYLTRIAZENE are not available, however, 1,3-DIPHENYLTRIAZENE is probably combustible.

Safety Profile

Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Strongly explosive when shocked or heated to 98'C. Mixture with acetic anhydride explodes when warmed. When heated to decomposition it emits toxic fumes of NOx,.

Carcinogenicity

Diazoaminobenzene is reasonably anticipated to be a human carcinogen based on (1) evidence from studies in experimental animals andwith human tissue demonstrating that diazoaminobenzene is metabolized to benzene, a known human carcinogen, and (2) evidence that diazoaminobenzene causes genetic damage. Studies in rats and mice have shown that the metabolism of diazoaminobenzene to benzene is quantitative. Benzene was listed in the First Annual Report onCarcinogens in 1980 based on human epidemiological studies dem-causes cancer at numerous tissue sites in rodents.

Environmental Fate

DAAB is a respiratory tract, skin, and eye irritant. DAAB yields benzene and aniline as metabolites. The proposed metabolic pathway forDAAB is that it is cleaved reductively by liver enzymes or gut flora to form aniline, benzene, and nitrogen. DAAB metabolism also results in the formation of a reactive phenyl radical, which could account for an additional risk of toxicity or carcinogenicity. The erythrocyte and lymphoid systems are major targets of DAAB toxicity. Induction of lymphoid atrophy of the thymus and other lymphoid tissues were observed, as well as methemoglobin formation, accompanying anemia, increased spleen weights, and regenerative hematopoiesis. Analysis of organ weights indicated possible chemical-related effects in the thymus, heart, spleen, kidney, and liver of rats and/or mice. Increases in the incidences of several skin lesions, including hyperplasia of the epidermis and hair follicles, and inflammation in rats and mice and ulceration in female mice were observed.

Toxicity evaluation

DAAB is an aromatic amine that exists as small golden yellow crystals at room temperature. It is insoluble in water (water solubility 0.5 g l^-1) but freely soluble in ethyl alcohol, ethyl ether, benzene, pyridine, and hexane. It is stable under normal temperatures and pressures. DAAB melts at 98°C, decomposes at 130°C with major decomposition at 188°C, and explodes at its boiling point of 150°C. When heated to decomposition, it emits toxic fumes of NOx. The decomposition products of DAAB include benzene, o- and p-aminodiphenyl, diphenylamine, and azobenzene.