Benzidine
描述
Benzidine is the organic compound with the formula (C6H4NH2)2. it is an aromatic amine. It is prepared in a two step process from nitrobenzene. First, the nitrobenzene is converted to 1,2-diphenylhydrazine, usually using iron powder as the reducing agent. Treatment of this hydrazine with mineral acids induces a rearrangement reaction to 4,4'-benzidine. Smaller amounts of other isomers are also formed. The benzidine rearrangement, which proceeds intramolecularly, is a classic mechanistic puzzle in organic chemistry. This aromatic amine is a component of a test for cyanide and also in the production of dyes. Benzidine has been linked to bladder and pancreatic cancer. Since August 2010 benzidine dyes are included in the EPA's List of Chemicals of Concern.
类别
"Industrial/Workplace Toxin", "Pollutant", "Airborne Pollutant", "Synthetic Toxin"
同义词
"4'-Amino[1,1'-biphenyl]-4-ylamine", "4, 4'-Biphenylenediamine", "4,4'-Bianiline", "4,4'-Biphenyldiamine", "4,4'-Biphenylenediamine", "4,4'-Diamino-1,1'-biphenyl", "4,4'-Diaminobiphenyl", "4,4'-Diaminodiphenyl", "4,4'-Diphenylenediamine", "Benzidin", "Biphenyl -4,4'-ylenediamine", "Fast Corinth Base B", "p,p'-Bianiline", "p,p'-Diaminobiphenyl", "p,p'-Dianiline", "p,p-Bianiline", "p-Diaminodiphenyl", "[1,1'-Biphenyl]-4,4'-diamine", "{[1,} 1'-Biphenyl]-4,4'-diamine"
IUPAC 名称
4-(4-aminophenyl)aniline
简化分子线性输入规范
NC1=CC=C(C=C1)C1=CC=C(N)C=C1
InChI 标识符
InChI=1S/C12H12N2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8H,13-14H2
键
InChIKey=HFACYLZERDEVSX-UHFFFAOYSA-N
类型
Benzene and substituted derivatives
子类
Biphenyls and derivatives
另外分类
"Aniline and substituted anilines", "Hydrocarbon derivatives", "Organopnictogen compounds", "Primary amines"
取代基
"Amine", "Aniline or substituted anilines", "Aromatic homomonocyclic compound", "Benzidine", "Hydrocarbon derivative", "Organic nitrogen compound", "Organonitrogen compound", "Organopnictogen compound", "Primary amine"
分子框架
Aromatic homomonocyclic compounds
地位
Detected and Not Quantified
蜂窝位置
"Cytoplasm", "Extracellular"
熔点/沸点/溶解度
120°C//0.322 mg/mL at 25°C
暴露途径
Oral (L95) ; inhalation (L95) ; dermal (L95)
毒性机制
N-acetylated benzidine metabolites are believed to form adducts with nucleic acids. Carcinogenesis is initiated when they are activated by peroxidation by prostaglandin H synthetase, oxidation by cytochrome P-450, or O-esterification by O-acetyltransferase or N,O-acetyltransferase. Benzidine has also been shown to bind to RNA and hemoglobin. (L95, A55)
代谢
Benzidine is absorpted following inhalation, oral, and dermal routes of exposure. Metabolism involves multiple and complex enzymatic pathways, including cytochrome P-450 and flavin monooxygenase systems, peroxidation by prostaglandin H synthase, and oxidation by lipoxygenases. The main reactions involved are N-acetylation, N-oxidation, and N-glucuronidation. Benzidine and its metabolites are excreted in the urine and faeces. (L95)
毒性值
LD50: 309 mg/kg (Oral, Rat) (T14)
LD50: 110 mg/kg (Intraperitoneal, Mouse) (T14)
致癌性
1, carcinogenic to humans. (L135)
用途/来源
Benzidine was used to produce dyes for cloth, paper, and leather. (L95)
健康影响
Benzidine is a known human carcinogen, most often associated with cancer of the urinary bladder. If benzidine comes in contact with skin it may cause a skin allergy. Liver, kidney, immune, and neurological effects have also been observed in animals exposed to benzidine. (L95)
维基百科链接
http://en.wikipedia.org/wiki/Benzidine
创建于
2009-03-06 18:57:56 UTC
更新于
2014-12-24 20:20:55 UTC