3,3'-Dichlorobenzidine (CHEM000036)

Record Information
Version1.0
Creation Date2009-03-06 18:57:58 UTC
Update Date2026-08-18 15:30:38 UTC
Accession NumberCHEM000036
Identification
Common Name3,3'-Dichlorobenzidine
ClassSmall 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
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,3-DichlorobenzidineMeSH
3,3' DichlorobenzidineMeSH
3,3 DichlorobenzidineMeSH
Chemical FormulaC12H10Cl2N2
Average Molecular Mass253.127 g/mol
Monoisotopic Mass252.022 g/mol
CAS Registry Number91-94-1
IUPAC Name4-(4-amino-3-chlorophenyl)-2-chloroaniline
Traditional Name3,3'-dichlorobenzidine
SMILESNC1=CC=C(C=C1Cl)C1=CC=C(N)C(Cl)=C1
InChI IdentifierInChI=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 KeyHUWXDEQWWKGHRV-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct Parent3,3'-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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceGray to purple crystalline solid.
Experimental Properties
PropertyValue
Melting Point132-133°C
Boiling PointNot Available
Solubility0.0031 mg/mL at 25 °C [BANERJEE,S et al. (1980)]
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.6ALOGPS
logP3.17ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)2.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.04 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.2 m³·mol⁻¹ChemAxon
Polarizability25.46 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (3)
Mechanism of Toxicity3,3’-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)
Metabolism3,3'-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 ValuesLD50: 8 g/kg (Dermal, Rat) (5) LD50: 3.82 g/kg (Oral, Rat) (5)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (4)
Uses/Sources3,3'-Dichlorobenzidine is used in pigments for printing inks, textiles, plastics and enamels, paint, leather, and rubber. (3)
Minimum Risk LevelNot Available
Health EffectsThe 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)
SymptomsThe salt form of 3,3'-dichlorobenzidine may cause sore throat, respiratory infections, stomach upset, headache, dizziness, caustic burns, and dermatitis. (3)
TreatmentTreatment for 3,3'-dichlorobenzidine poisoning is usually supportive. (3)
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0245999
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link3,3'-Dichlorobenzidine
Chemspider ID6803
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDC19225
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References