| Description | Diazoaminobenzene (DAAB) is an aromatic amine that isa suspected carcinogen. It is harmful if inhaled, ingested, orabsorbed through the skin. It causes skin irritation and severeirritation to eyes. DAAB can be made by diazotizing anilinedissolved in hydrochloric acid with sodium nitrite and thenadding a concentrated solution of sodium acetate. DAAB islisted in the US Environmental Protection Agency’s ToxicSubstances Control Act Inventory. DAAB has three major useareas: intermediate, complexing agent, and polymer additive.Use as an intermediate is reported in several industry sectors,including organic synthesis, dye manufacture, and agrochemicalmanufacture (insecticides). DAAB is also a versatile metalcomplexing agent. A series of metabolism studies in rodentsand human liver slices, electron spin resonance spectroscopystudies, short-term dermal toxicity studies in rodents, and acutebone marrow micronucleus studies in mice demonstrated thatDAAB is metabolized and shares similar genotoxic and toxicologicalproperties to the known human carcinogen, benzene,and the known rodent carcinogen, aniline. |
| Chemical Properties | ochre powder |
| Uses | DAAB is used as a chemical intermediate, a complexing agent,and as a polymer additive. DAAB has been used to promoteadhesion of natural rubber to steel tire cords. It has also beenused as a blowing agent in the production of a foamed polymericmaterial. In addition, DAAB is used in the manufactureof dyes and insecticides. DAAB is also an impurity in certaincolor additives used in cosmetics, food products, and pharmaceuticals.In addition, it has been reported to show semiconductingproperties and to be useful as a dopant for polymethylmethacrylate in semiconductor manufacture. |
| Uses | 1,3-Diphenyltriazene can be used to prepare degradable polyester foam material. |
| 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). |
| 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 yieldsbenzene and aniline as metabolites. The proposed metabolicpathway forDAAB is that it is cleaved reductively by liver enzymesor gut flora to form aniline, benzene, and nitrogen. DAABmetabolism also results in the formation of a reactive phenylradical, which could account for an additional risk of toxicity orcarcinogenicity. The erythrocyte and lymphoid systems are majortargets of DAAB toxicity. Induction of lymphoid atrophy of thethymus and other lymphoid tissues were observed, as well asmethemoglobin formation, accompanying anemia, increasedspleen weights, and regenerative hematopoiesis. Analysis oforgan weights indicated possible chemical-related effects in thethymus, heart, spleen, kidney, and liver of rats and/or mice.Increases in the incidences of several skin lesions, includinghyperplasia of the epidermis and hair follicles, and inflammationin rats and mice and ulceration in female mice were observed. |
| Toxicity evaluation | DAAB is an aromatic amine that exists as small golden yellowcrystals at room temperature. It is insoluble in water (watersolubility 0.5 g l-1) but freely soluble in ethyl alcohol, ethylether, benzene, pyridine, and hexane. It is stable under normaltemperatures and pressures. DAAB melts at 98°C, decomposesat 130°C with major decomposition at 188°C, and explodes atits boiling point of 150°C. When heated to decomposition, itemits toxic fumes of NOx. The decomposition products ofDAAB include benzene, o- and p-aminodiphenyl, diphenylamine,and azobenzene. |
