4-Aminobiphenyl

4-Aminobiphenyl
Names
Preferred IUPAC name
[1,1′-Biphenyl]-4-amine
Other names
4-Aminobiphenyl, xenylamine, 4-ABP
4-Aminodiphenyl[1]
p-Aminobiphenyl[1]
p-Aminodiphenyl[1]
4-Phenylaniline[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.980 Edit this at Wikidata
EC Number
  • 202-177-1
KEGG
RTECS number
  • DU8925000
UNII
UN number 3077
  • InChI=1S/C12H11N/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,13H2 checkY
    Key: DMVOXQPQNTYEKQ-UHFFFAOYSA-N checkY
  • InChI=1/C12H11N/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,13H2
    Key: DMVOXQPQNTYEKQ-UHFFFAOYAX
  • c1ccccc1c2ccc(N)cc2
Properties
C12H11N
Molar mass 169.227 g·mol−1
Appearance White solid
Odor Floral[1]
Density 1.16 g/cm3[2]
Melting point 52 to 54 °C (126 to 129 °F; 325 to 327 K)[2]
Boiling point 302 °C (576 °F; 575 K)[2]
Slightly soluble in cold water, soluble in hot water[3]
Vapor pressure 20 mbar (191 °C)[2]
Acidity (pKa) 4.35 (conjugate acid; 18 °C, H2O)[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 potential occupational carcinogen[1]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 147 °C (297 °F; 420 K)
450 °C (842 °F; 723 K)
NIOSH (US health exposure limits):
REL (Recommended)
 carcinogen[1]
IDLH (Immediate danger)
 N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

4-Aminobiphenyl (4-ABP) is an organic compound with the formula C6H5C6H4NH2. It is an amine derivative of biphenyl. It is a colorless solid, although aged samples can appear colored. 4-Aminobiphenyl was commonly used in the past as a rubber antioxidant and an intermediate for dyes.[5] Exposure to this aryl-amine can happen through contact with chemical dyes and from inhalation of cigarette smoke.[6] Researches showed that 4-aminobiphenyl is responsible for bladder cancer in humans and dogs by damaging DNA.[7] Due to its carcinogenic effects, commercial production of 4-aminobiphenyl ceased in the United States in the 1950s.[8]

  1. ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0025". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b c d Record of CAS RN 92-67-1 in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 8. April 2009.
  3. ^ Humans, IARC Working Group on the Evaluation of Carcinogenic Risk to (2010). Some Aromatic Amines, Organic Dyes, and Related Exposures. International Agency for Research on Cancer.
  4. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 978-1498754286.
  5. ^ Humans, IARC Working Group on the Evaluation of Carcinogenic Risk to (2012). 4-AMINOBIPHENYL. International Agency for Research on Cancer.
  6. ^ Radomski, J.L. (1979). "The Primary Aromatic Amines: Their Biological Properties and Structure-Activity Relationships". Annual Review of Pharmacology and Toxicology. 19: 129–157. doi:10.1146/annurev.pa.19.040179.001021. PMID 378100.
  7. ^ Babu, S.R. (1996). "Glucuronide Conjugates of +Aminobiphenyl and Its Hydroxy Metabolites". Biochemical Pharmacology. 51 (12): 1679–1685. doi:10.1016/0006-2952(96)00165-7. PMID 8687483.
  8. ^ Koss, L.G. (1969). "Further cytologic and histologic studies of bladder lesions in workers exposed to para-aminodiphenyl: progress report". Journal of the National Cancer Institute. 43 (1): 233–243. doi:10.1002/ijc.21173. PMID 15880493.