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Name Description
id 24
T3DB ID T3D0026
Name Benzidine
Class SmallMolecule
Description 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.
Categories "Industrial/Workplace Toxin", "Pollutant", "Airborne Pollutant", "Synthetic Toxin"
Types "Organic Compound", "Aromatic Hydrocarbon", "Amine", "Pollutant", "Metabolite", "Industrial/Workplace Toxin", "Synthetic Compound"
Synonyms "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"
CAS Number 92-87-5
Chemical Formula C12H12N2
Average Molecular Mass 184.24
Monoisotopic Mass 184.10
IUPAC Name 4-(4-aminophenyl)aniline
Traditional Name benzidine
SMILES NC1=CC=C(C=C1)C1=CC=C(N)C=C1
InChI Identifier InChI=1S/C12H12N2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8H,13-14H2
InChI Key InChIKey=HFACYLZERDEVSX-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Benzenoids
Class Benzene and Substituted Derivatives
Sub Class Biphenyls and Derivatives
Direct Parent Biphenyls and Derivatives
Alternate Parents "Substituted Anilines", "Primary Aromatic Amines"
Geometric Description Aromatic Homomonocyclic Compounds
Substituents "aniline", "primary aromatic amine", "primary amine", "organonitrogen compound", "Aromatic Homomonocyclic Compound", "Amine", "Substituted Aniline", "Benzidine"
Descriptors
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Cytoplasm", "Extracellular"
Biofluids
Tissues
Pathways
State Solid
Appearance White powder.
Melting Point 120°C
Boiling Point
Solubility 0.322 mg/mL at 25°C
LogP 1.34
Route of Exposure Oral (L95) ; inhalation (L95) ; dermal (L95)
Mechanism of Toxicity 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)
Metabolism 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)
Toxicity LD50: 309 mg/kg (Oral, Rat) (T14) LD50: 110 mg/kg (Intraperitoneal, Mouse) (T14)
Lethal Dose
Carcinogenicity 1, carcinogenic to humans. (L135)
Uses/Sources Benzidine was used to produce dyes for cloth, paper, and leather. (L95)
Minimum Risk Level
Health Effects 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)
Symptoms
Treatment
DrugBank ID
HMDB ID HMDB41835
PubChem Compound ID 7111
ChEMBL ID CHEMBL15901
ChemSpider ID 6844
KEGG Compound ID C16444
UniProt ID 0
OMIM ID 0
ChEBI ID 0
BioCyc ID
CTD ID C029876
Stitch ID Benzidine
PDB ID
ACToR ID 139
Wikipedia Link http://en.wikipedia.org/wiki/Benzidine
Creation Date 2009-03-06 18:57:56
Update Date 2014-12-24 20:20:55