92-67-1

Colorless to yellowish-brown crystals or light brown solid.

4-AMINOBIPHENYL(92-67-1) is a weak base. Incompatible with acids and acid anhydrides. Forms salts with hydrochloric acid and sulfuric acid. Can be diazotized, acetylated and alkylated. . May react with strong oxidizing agents.

Is oxidized by air (darkens on oxidation). Insoluble in water.

Toxic by ingestion, inhalation, skin absorp- tion. Confirmed carcinogen. Bladder and liver can- cer.

4-Aminobiphenyl is no longer manufactured commercially and is only used for research purposes. 4-Aminobiphenyl was formerly used as a rubber antioxidant and as a dye intermediate. Is a contaminant in 2-aminobiphenyl.

This chemical is probably combustible.

Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3143 Dyes, solid, toxic, n.o.s. or Dye intermediates, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides and acid anhydrides.

4-Aminobiphenyl is a combustible, colorless to tan crystalline solid that turns purple on exposure to air. May be used in a liquid solution. Floral odor.

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Controlled incineration whereby oxides of nitrogen are removed from the effluent gas by scrubber, catalytic or thermal devices.

Colorless to yellow-brown crystalline solid with a floral-like odor. Becomes purple on exposure to air.

ChEBI: An aminobiphenyl that is biphenyl substituted by an amino group at position 4.

Because of its carcinogenic effects, 4-aminobiphenyl has not been produced commercially in the United States since the mid 1950s (Koss et al. 1969). It was present in the drug and cosmetic color additive D&C yellow no. 1; however, use of this color additive was discontinued in the late 1970s (HSDB 2009). 4-Aminobiphenyl has beenreported to be formed by the decomposition of 1,3-diphenyltriazeneproduced by the reaction of diazoaniline and aniline during manufacture of the dye D&C red no. 33 (Bailey 1985). In 2009, 4-aminobiphenyl (for use in research) was available from 11 U.S. suppliers, including one company that supplied bulk quantities (ChemSources 2009). 4-Aminobiphenyl also has been reported as a contaminant in diphenylamine (HSDB 2009).

Journal of the American Chemical Society, 97, p. 7184, 1975 DOI: 10.1021/ja00857a049
Tetrahedron Letters, 39, p. 1313, 1998 DOI: 10.1016/S0040-4039(97)10877-2

4-Aminodiphenyl exposure is associated with a high incidence of bladder cancer in humans.

4-aminobiphenyl is prepared by reduction of 4-nitrobiphenyl, which, together with the 2-nitro derivatives, is obtained by nitration of biphenyl.

4-Aminobiphenyl is known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans.
Cancer of the urinary bladder was first reported to be associated with occupational exposure to 4-aminobiphenyl in a descriptive epidemiological study (published in the mid 1950s), in which 11% (19 of 171) of workers in a plant manufacturing 4-aminobiphenyl developed urinary-bladder cancer. These workers had been exposed to 4-aminobiphenyl for 1.5 to 19 years between 1935 and 1955. Publication of this study led to an effort to discontinue production and useof 4-aminobiphenyl. Starting in 1955, 541 workers who had been exposed to 4-aminobiphenyl were followed for an additional 14 years; 43 men (7.9%) developed histologically confirmed urinary-bladder cancer. In a survey of workers at a plant producing a variety of chemicals, the risk of mortality from urinary-bladder cancer was elevated tenfold, and all of the men who died of urinary-bladder cancer had worked at the plant during the period when 4-aminobiphenyl was used (1941 through 1952). The International Agency for Research onCancer concluded that there was sufficient evidence of the carcinogenicity of 4-aminobiphenyl in humans (IARC 1972, 1987).
Since 4-aminobiphenyl was listed in the First Annual Report on Carcinogens, most research on its carcinogenicity has focused on exposure from cigarette smoking. Epidemiological studies have reported the incidence of urinary-bladder cancer to be 2 to 10 times as high among cigarette smokers as among nonsmokers. Higher levels of 4-aminobiphenyl adducts (4-aminobiphenyl metabolites bound to DNA or protein) were detected in bladder tumors (DNA adducts) and red blood cells (hemoglobin adducts) from smokers thanfrom nonsmokers (Feng et al. 2002). In a case-control study, levels of 4-aminobiphenyl–hemoglobin adducts were higher in smokers with urinary-bladder cancer than in a control group of similarly exposed smokers (Del Santo et al. 1991). A Taiwanese study reported that 4-aminobiphenyl–hemoglobin adducts were associated with increased risk of liver cancer (Wang et al. 1998).

4-Aminobiphenyl is one of a number of chemicals that cause methemoglobinemia, or conversion of hemoglobin to methemoglobin, which reduces the ability of the blood to carry oxygen to the tissues. In addition, the active metabolite is believed to produce cancer through its reaction with cellular DNA. In animal studies, the observed incidence of 4-aminobiphenyl adducts with bladder epithelium DNA correlated well with the observed bladder tumor incidence.

Ring oxidation of 4-aminobiphenyl occurred only to a minor extent in microsomes. In contrast, N-oxidation of 4,4'-methylene-bis-(2-chloroaniline) is preferentially catalyzed by the phenobarbital-induced enzymes P- 450PB-B and P-450PB-D to cause ring oxidation and methylene carbon oxidation. 4,4'-Methylene-bis-(2- chloroaniline) ring oxidation and methylene carbon oxidation show varied cytochrome P-450 selectivity and accounted for 14-79% of total oxidation products.

Crystallise it from water or EtOH. [Beilstein 12 IV 3241.] CARCINOGENIC.

4-Aminobiphenylmay have been released into the environment during its production and use as a rubber antioxidant and dye intermediate; however, sources suggest that it was no longer in significant production by the early 1970s. 4-Aminobiphenyl is easily oxidizable and probably undergoes photolysis but there is little actual data on these processes. If released on land it is expected to adsorb moderately to soil, probably binding to humic materials, and undergo redox reactions. If released to surface water, it is expected to adsorb to sediment, and probably undergo photolysis and oxidation. It may be degraded by oxidation by alkoxy radicals, which are photochemically produced in eutrophic waters, with an estimated half-life of 14 days. 4-Aminobiphenyl is biodegradable and biodegradation may well occur in both soil and water but there are no rates available for soil or surface waters. It has a low potential for bioconcentration. In the atmosphere, degradation should occur due to direct photolysis, oxidation by ambient oxygen, and photochemically produced hydroxyl radicals (estimated half-life 6–7 h in the vapor phase).