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 Å²
H-bond donors: 2
H-bond acceptors: 2
Formal charge: 0

via PubChem

Wikidata facts

Mass: 184.1

Show 12 more facts

Commons category: Benzidine
chemical formula: C₁₂H₁₂N₂
median lethal dose (LD50): 309
NIOSH Pocket Guide ID: 0051
density: 1.25
melting point: 120
boiling point: 752
solubility: 0.04
ceiling exposure limit: 0.008
minimal lethal dose: 200
time-weighted average exposure limit: 0.001
canonical SMILES: C1=CC(=CC=C1C2=CC=C(C=C2)N)N

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Article

5 sections

Contents

Synthesis and properties
Applications
Related 4,4’-benzidines
Safety
References

==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