ChemFOnt: Showing chemical card for Benzidine (CFc000022687)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:15:06 UTC

Chemfont ID

CFc000022687

Molecule Identification

Common Name

Benzidine

Definition

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. Benzidine, the trivial name for 4,4'-diaminobiphenyl, is the solid organic compound with the formula (C6H4NH2)2. 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1,1'-Biphenyl)-4,4'-diamine	ChEBI
4,4'-Bianiline	ChEBI
4,4'-Biphenyldiamine	ChEBI
4,4'-Biphenylenediamine	ChEBI
4,4'-Diamino-1,1'-biphenyl	ChEBI
4,4'-Diaminobiphenyl	ChEBI
4,4'-Diaminodiphenyl	ChEBI
4,4'-Diphenylenediamine	ChEBI
C.I. azoic diazo component 112	ChEBI
p,P'-bianiline	ChEBI
p,P'-diaminodiphenyl	ChEBI
p-Diaminodiphenyl	ChEBI
4'-Amino[1,1'-biphenyl]-4-ylamine (acd/name 4.0)	HMDB
4, 4'-Biphenylenediamine	HMDB
Biphenyl -4,4'-ylenediamine	HMDB
Fast corinth base b	HMDB
p,P'-diaminobiphenyl	HMDB
p,P'-dianiline	HMDB
p,p-Bianiline	HMDB
Rcra waste number u021	HMDB
[1,1'-Biphenyl]-4,4'-diamine	HMDB
[1,1'-Biphenyl]-4,4'-diamine (acd/name 4.0)	HMDB
{[1,} 1'-biphenyl]-4,4'-diamine	HMDB
Benzidine hydrochloride	HMDB
Benzidine acetate	HMDB
Benzidine monosulfate	HMDB
Benzidine dihydrochloride	HMDB

Chemical Formula

C₁₂H₁₂N₂

Average Molecular Weight

184.2371

Monoisotopic Molecular Weight

184.100048394

IUPAC Name

4-(4-aminophenyl)aniline

Traditional Name

benzidine

CAS Registry Number

92-87-5

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

HFACYLZERDEVSX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzidines. These are organic compounds containing the benzidine skeleton, made up of a biphenyl ring system substituted at the 4- and 4'-positions with a unsubstituted amine group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Benzidines

Alternative Parents

Substituents

Benzidine
Aniline or substituted anilines
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

biphenyls (CHEBI:80495 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0041835)
Extracellular (HMDB: HMDB0041835)

Source

Exogenous

Exogenous (HMDB: HMDB0041835)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.4 g/L	ALOGPS
logP	1.59	ALOGPS
logP	1.96	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	4.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.04 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.6 m³·mol⁻¹	ChemAxon
Polarizability	21.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041835

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6844

KEGG Compound ID

C16444

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzidine

METLIN ID

Not Available

PubChem Compound

7111

PDB ID

Not Available

ChEBI ID

80495

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Benzidine (CFc000022687)

MOL for CFc000022687 (Benzidine)

3D MOL for CFc000022687 (Benzidine)

3D SDF for CFc000022687 (Benzidine)

3D-SDF for CFc000022687 (Benzidine)

PDB for CFc000022687 (Benzidine)

3D PDB for CFc000022687 (Benzidine)

SMILES for CFc000022687 (Benzidine)

INCHI for CFc000022687 (Benzidine)

Structure for CFc000022687 (Benzidine)

3D Structure for CFc000022687 (Benzidine)