| Identification | More | [Name]
4-AMINOBIPHENYL | [CAS]
92-67-1 | [Synonyms]
[1,1'-BIPHENYL]-4-AMINE
4-AMINOBIPHENYL
4-BIPHENYLAMINE
4-BIPHENYLYLAMINE
4-PHENYLANILINE
AKOS BBS-00000786
BIPHENYL-4-YLAMINE HYDROCHLORIDE
LABOTEST-BB LTBB000626
p-Aminophenylbenzene
4-adp
4-Aminobifenyl
4-aminobiphenyle
4-Aminodifenil
4-Aminodiphenyl
4-Bifenylamin
Aniline, p-phenyl-
biphenyl-4-ylamine
Biphenylamine
p-Aminobiphenyl
p-Aminodiphenyl | [EINECS(EC#)]
202-177-1 | [Molecular Formula]
C12H11N | [MDL Number]
MFCD00007879 | [Molecular Weight]
169.22 | [MOL File]
92-67-1.mol |
| Chemical Properties | Back Directory | [Description]
4-Aminobiphenyl is an aromatic amine (arylamine) that exists at room temperature as a colorless crystalline solid with a floral odor. It is slightly soluble in cold water, but readily soluble in hot water. It is soluble in ethanol, ether, acetone, chloroform, and lipids. It oxidizes in air and emits toxic fumes when heated to decomposition (Akron 2009). | [Appearance]
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. | [Melting point ]
52-54 °C(lit.)
| [Boiling point ]
191 °C15 mm Hg(lit.)
| [density ]
1.1154 (rough estimate) | [vapor pressure ]
6 x 10-5 mmHg at 20–30 °C (quoted, Mercer et al., 1990) | [refractive index ]
1.5785 (estimate) | [Fp ]
>110°C | [storage temp. ]
-20°C Freezer | [solubility ]
Soluble in Dichloromethane, DMSO and Methanol | [form ]
powder | [pka]
4.35(at 18℃) | [color ]
Brown to Dark Yellow | [Stability:]
Stable, but slowly reacts with oxygen in the air. Combustible. Incompatible with strong oxidizing agents, acids, acid anhydrides, acid chlorides. | [Water Solubility ]
842 mg/L at 20–30 °C (quoted, Mercer et al., 1990) | [Usage]
Induces chromosomal instability in human cancer cells. | [Merck ]
13,1235 | [BRN ]
386533 | [Henry's Law Constant]
(x 1010 atm?m3/mol):
3.89 at 25 °C (calculated, Mercer et al., 1990) | [InChIKey]
DMVOXQPQNTYEKQ-UHFFFAOYSA-N | [Uses]
In the United States, 4-aminobiphenyl now is used only in laboratoryresearch. It formerly was used commercially as a rubber antioxidant, as a dye intermediate, and in the detection of sulfates (HSDB 2009). | [CAS DataBase Reference]
92-67-1(CAS DataBase Reference) | [IARC]
1 (Vol. 1, Sup 7, 99, 100F) 2012 | [NIST Chemistry Reference]
4-Aminobiphenyl(92-67-1) | [EPA Substance Registry System]
92-67-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xn | [Risk Statements ]
R45:May cause cancer.
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 3077 9/PG 3
| [WGK Germany ]
3
| [RTECS ]
DU8925000
| [Autoignition Temperature]
842 °F | [TSCA ]
Yes | [HazardClass ]
6.1(a) | [PackingGroup ]
I | [HS Code ]
29214990 | [Safety Profile]
Confirmed human carcinogen with experimental carcinogenic and tumorigenic data. Poison by ingestion and intraperitoneal routes. Human mutation data reported. An irritant. Effects resemble those of benzidine. See also BENZIDINE. Slight to moderate fire hazard when exposed to heat, flames (sparks), or powerful oxidzers. To fight fire, use water spray, mist, dry chemical. When heated to decomposition it emits toxic fumes of NOx,. See also AROMATIC AMINES. | [Hazardous Substances Data]
92-67-1(Hazardous Substances Data) | [Toxicity]
Acute oral LD50 for rats 200 mg/kg, mice 50 mg/kg (quoted, Verschueren, 1983). |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Potassium carbonate-->Sodium hypochlorite-->Triphenylphosphine-->Biphenyl-->Palladium (II) Acetate-->Diphenylphosphoryl azide-->4-Bromoaniline-->4-Biphenylcarboxylic acid-->Phenylboronic acid-->4-Nitrobiphenyl | [Preparation Products]
Acid Orange 67-->4-Iodobiphenyl-->4-methoxy-2-phenylaniline-->N-(4-biphenyl)-(9,9-dimethylfluoren-2--yl)Amine-->[1,1':2',1''-Terphenyl]-4'-amine-->[1,1'-Biphenyl]sulfonic acid, 4,4''-[(9,10-dihydro-9,10-dioxo-1,4-anthracenediyl)diimino]bis-, disodium salt |
| Hazard Information | Back Directory | [General Description]
Colorless to yellowish-brown crystals or light brown solid. | [Reactivity Profile]
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. | [Air & Water Reactions]
Is oxidized by air (darkens on oxidation). Insoluble in water. | [Hazard]
Toxic by ingestion, inhalation, skin absorp-
tion. Confirmed carcinogen. Bladder and liver can-
cer.
| [Potential Exposure]
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. | [Fire Hazard]
This chemical is probably combustible. | [First aid]
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. | [Shipping]
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 | [Incompatibilities]
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. | [Chemical Properties]
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. | [Waste Disposal]
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.
| [Physical properties]
Colorless to yellow-brown crystalline solid with a floral-like odor. Becomes purple on exposure to
air. | [Definition]
ChEBI: An aminobiphenyl that is biphenyl substituted by an amino group at position 4. | [Production Methods]
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). | [Synthesis Reference(s)]
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 | [Health Hazard]
4-Aminodiphenyl exposure is
associated with a high incidence of bladder
cancer in humans. | [Synthesis]
4-aminobiphenyl is prepared by reduction of 4-nitrobiphenyl, which, together with the 2-nitro derivatives, is obtained by nitration of biphenyl.
| [Carcinogenicity]
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). | [Environmental Fate]
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. | [Metabolic pathway]
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. | [Purification Methods]
Crystallise it from water or EtOH. [Beilstein 12 IV 3241.] CARCINOGENIC. | [Toxicity evaluation]
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). |
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