4-aminobiphenyl
Also known as p-Aminodiphenyl, 4-Phenylaniline, 4-amino-1,1'-biphenyl, p-Aminobiphenyl, (1,1'-Biphenyl)-4-amine, Xenylamine, Biphenylamine, 4-Aminodiphenyl
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. Exposure to this aryl-amine can happen through contact with chemical dyes and from inhalation of cigarette smoke. Researches showed that 4-aminobiphenyl is responsible for bladder cancer in humans and dogs by damaging DNA. Due to its carcinogenic effects, commercial production of 4-aminobiphenyl ceased in the United
Research
907 papers- Secondhand smoking, 4-aminobiphenyl, and bladder cancer: two meta-analyses.Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology · 2009
- 4-Aminobiphenyl and DNA reactivity: case study within the context of the 2006 IPCS Human Relevance Framework for Analysis of a cancer mode of action for humans.Critical reviews in toxicology · 2006
- 4-Aminobiphenyl.Report on carcinogens : carcinogen profiles · 2004
- 4-Aminobiphenyl.Report on carcinogens : carcinogen profiles · 2011
- 4-Aminobiphenyl.Report on carcinogens : carcinogen profiles · 2002
via PubMed
Article
9 sectionsContents
- Synthesis and reactivity
- Mechanism of action
- General mechanism
- 4-ABP leading to mutation in p53 gene
- Metabolism process in humans
- Toxicity
- Human toxicity
- Animal toxicity
- References
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. Exposure to this aryl-amine can happen through contact with chemical dyes and from inhalation of cigarette smoke. Researches showed that 4-aminobiphenyl is responsible for bladder cancer in humans and dogs by damaging DNA. Due to its carcinogenic effects, commercial production of 4-aminobiphenyl ceased in the United States in the 1950s.
==Synthesis and reactivity== Like other aniline derivatives, 4-aminobiphenyl is weakly basic. It is prepared by reduction of 4-nitrobiphenyl: