benzidine
Also known as 4,4'-Bianiline, 4,4'-Biphenyldiamine, 1,1'-Biphenyl-4,4'-diamine, 4,4'-Diaminobiphenyl, p-Diaminodiphenyl, 4,4'-Biphenylenediamine, 4,4'-Diamino-1,1'-biphenyl, 4,4'-Diaminodiphenyl
Benzidine (trivial name), also called '''1,1'-biphenyl-4,4'-diamine''' (systematic name), is an organic compound with the formula (C6H4NH2)2. It is an aromatic amine. It is a component of a test for cyanide. Related derivatives are used in the production of dyes. Benzidine has been linked to bladder and pancreatic cancer.
Chemical data
- Formula
- C12H12N2
- Molecular weight
- 184.24 g/mol
- IUPAC name
- 4-(4-aminophenyl)aniline
- SMILES
- C1=CC(=CC=C1C2=CC=C(C=C2)N)N
- InChIKey
- HFACYLZERDEVSX-UHFFFAOYSA-N
- XLogP
- 1.3
- Polar surface area
- 52 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Article
5 sectionsContents
- Synthesis and properties
- Applications
- Related 4,4’-benzidines
- Safety
- References
Benzidine (trivial name), also called '''1,1'-biphenyl-4,4'-diamine''' (systematic name), is an organic compound with the formula (C6H4NH2)2. It is an aromatic amine. It is a component of a test for cyanide. Related derivatives are used in the production of dyes. Benzidine has been linked to bladder and pancreatic cancer.
==Synthesis and properties== Benzidine 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. 400px