ContaminantDB: 3,3'-Dichlorobenzidine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (50)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:57:58 UTC

Update Date

2026-03-27 02:14:36 UTC

Accession Number

CHEM000036

Identification

Common Name

3,3'-Dichlorobenzidine

Class

Small Molecule

Description

3,3'-Dichlorobenzidine is a manufactured chemical used in pigments for printing inks, textiles, plastics and enamels, paint, leather, and rubber. (3)

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 2B
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Aromatic Hydrocarbon
Industrial Precursor/Intermediate
Industrial/Workplace Toxin
Organic Compound
Organochloride
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,3-Dichlorobenzidine	MeSH
3,3' Dichlorobenzidine	MeSH
3,3 Dichlorobenzidine	MeSH

Chemical Formula

C₁₂H₁₀Cl₂N₂

Average Molecular Mass

253.127 g/mol

Monoisotopic Mass

252.022 g/mol

CAS Registry Number

91-94-1

IUPAC Name

4-(4-amino-3-chlorophenyl)-2-chloroaniline

Traditional Name

3,3'-dichlorobenzidine

SMILES

NC1=CC=C(C=C1Cl)C1=CC=C(N)C(Cl)=C1

InChI Identifier

InChI=1S/C12H10Cl2N2/c13-9-5-7(1-3-11(9)15)8-2-4-12(16)10(14)6-8/h1-6H,15-16H2

InChI Key

HUWXDEQWWKGHRV-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 3,3'-disubstituted benzidines. These are organic compounds containing a benzidine skeleton, which is substituted only at the 3- and 3'-positions.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

3,3'-disubstituted benzidines

Alternative Parents

Substituents

3,3'-disubstituted benzidine
Polychlorinated biphenyl
Chlorinated biphenyl
Aniline or substituted anilines
Halobenzene
Chlorobenzene
Aryl halide
Aryl chloride
Amine
Primary amine
Organopnictogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organochlorine compound (CHEBI:82315 )
biphenyls (CHEBI:82315 )
monochlorobenzenes (CHEBI:82315 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Gray to purple crystalline solid.

Experimental Properties

Property	Value
Melting Point	132-133°C
Boiling Point	Not Available
Solubility	0.0031 mg/mL at 25 °C [BANERJEE,S et al. (1980)]

Predicted Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	3.6	ALOGPS
logP	3.17	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	2.95	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	70.2 m³·mol⁻¹	ChemAxon
Polarizability	25.46 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-1190000000-24f73fe267571f991098	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-0950000000-e1d8ac0da5f211c65d65	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0f89-0920000000-a0acaebe463099f8c45d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udi-0390000000-a504760a935655f0ad6e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-e14c2cb52287428839f2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014i-0090000000-44b7f2dc526920f9e3e3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-2da30e4a6dae2b880e5e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0090000000-d03397aa4295ebecf622	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0itc-0950000000-5e7d8b51b049c2f2b5f9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-1dcd7bb117f620a82c50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-9f8332f0967b437df6ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uxr-1190000000-1624efdbdce5c9812b31	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-ad50fe771c7f0687b3dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0190000000-2d307ba5c02f87017af3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-016u-0950000000-98304cf4c8eb8aac02f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-2090000000-a02e0d659edcaa44b74c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ue9-5190000000-b984bc558f86e89cff59	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9100000000-dd9cc100e68f2a032543	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-2490000000-b903f233a630b1efdf6d	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (3) ; inhalation (3) ; dermal (3)

Mechanism of Toxicity

3,3’-Dichlorobenzidine's mechanism of toxicity derives mainly from the adduction of DNA by its metabolites. The formation of nitroso derivatives during metabolism, yielding a sulfinic acid amide with hemoglobin in erythrocytes, is suggested to be a mechanism for this adduct formation. 3,3’-Dichlorobenzidine can act on the aryl hydrocarbon receptor to induce the activity of cytochrome p-450 enzymes, which metabolize 3,3’-dichlorobenzidine, along with other polyhalogenated aromatics, into their toxic intermediates. (3, 1, 2)

Metabolism

3,3'-Dichlorobenzidine is absorbed via ingestion, inhalation, and dermal routes. The major path of metabolism is believed to be N-acetylation via hepatic N-acetyltransferases, producing metabolites such as N-acetyl-3,3’-dichlorobenzidine and N,N-diacetyl-3,3’-dichlorobenzidine. 3,3'-Dichlorobenzidine may also be activated to toxic intermediates by certain cytochrome P-450 monooxygenases. Metabolites are excreted primarily in urine and to a lesser extent in faeces. (3)

Toxicity Values

LD50: 8 g/kg (Dermal, Rat) (5) LD50: 3.82 g/kg (Oral, Rat) (5)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (4)

Uses/Sources

3,3'-Dichlorobenzidine is used in pigments for printing inks, textiles, plastics and enamels, paint, leather, and rubber. (3)

Minimum Risk Level

Not Available

Health Effects

The salt form of 3,3'-dichlorobenzidine may cause respiratory infections, stomach upset, and dermatitis. 3,3'-Dichlorobenzidine is also believed to be a possible carcinogen. (3)

Symptoms

The salt form of 3,3'-dichlorobenzidine may cause sore throat, respiratory infections, stomach upset, headache, dizziness, caustic burns, and dermatitis. (3)

Treatment

Treatment for 3,3'-dichlorobenzidine poisoning is usually supportive. (3)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0245999

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

3,3'-Dichlorobenzidine

Chemspider ID

6803

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

C19225

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

3,3'-Dichlorobenzidine (CHEM000036)

Structure for CHEM000036: 3,3'-Dichlorobenzidine