4-Aminobiphenyl (CHEM000203)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2009-03-06 18:58:20 UTC
Update Date2026-04-03 01:07:18 UTC
Accession NumberCHEM000203
Identification
Common Name4-Aminobiphenyl
ClassSmall Molecule
Description4-Aminobiphenyl is an amine derivative of biphenyl. It is used to manufacture azo dyes. It is a known human carcinogen and so it has been largely replaced by less toxic compounds. It is similar to benzidine.
Contaminant Sources
  • Clean Air Act Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 1
  • My Exposome Chemicals
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Aromatic Hydrocarbon
  • Cigarette Toxin
  • Food Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-Amino-1,1'-biphenylChEBI
4-AminodiphenylChEBI
4-BiphenylamineChEBI
Biphenyl-4-ylamineChEBI
p-AminodiphenylChEBI
p-BiphenylamineChEBI
p-PhenylanilineChEBI
p-XenylamineChEBI
ParaaminodiphenylChEBI
(1,1'-Biphenyl)-4-amineHMDB
(4-Phenyl-phenyl)-amineHMDB
4-AminobifenylHMDB
4-AminodifenilHMDB
4-BifenylaminHMDB
4-Biphenylamine hydrochlorideHMDB, MeSH
4-BiphenylylamineHMDB
4-PhenylanilineHMDB
AminobiphenylHMDB
Biphenyl-4-amineHMDB
BiphenylamineHMDB
P-AminobiphenylHMDB
XenylaminHMDB
XenylamineHMDB
[1,1'-Biphenyl]-4-amineHMDB
[1,1'-Biphenyl]-4-amine (acd/name 4.0)HMDB
[1,1'-Biphenyl]-4-ylamine (acd/name 4.0)HMDB
{[1,1'-biphenyl]-4-amine}HMDB
4-Biphenylnitrenium ionMeSH, HMDB
4-AminobiphenylChEBI
Chemical FormulaC12H11N
Average Molecular Mass169.222 g/mol
Monoisotopic Mass169.089 g/mol
CAS Registry Number92-67-1
IUPAC Name[1,1'-biphenyl]-4-amine
Traditional Name4-aminobiphenyl
SMILESNC1=CC=C(C=C1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C12H11N/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,13H2
InChI KeyDMVOXQPQNTYEKQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentBiphenyls and derivatives
Alternative Parents
Substituents
  • Biphenyl
  • Aniline or substituted anilines
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • 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 Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point53.5°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.89ALOGPS
logP2.79ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)4.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity55.89 m³·mol⁻¹ChemAxon
Polarizability19.49 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-6900000000-485d158d46307e7e68a3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-6900000000-485d158d46307e7e68a3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1900000000-7cc97adc9c729451bd04Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-ea4ddfd09aa02c5ce68dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-bf153c3905690bdc5b59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-3900000000-2b96b507b444a3cfbeffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-8b7346091e37cac9abd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-8b7346091e37cac9abd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2900000000-c5ddef1d7d563f1bb3d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-f04809ed8d3ffdb9e395Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-f04809ed8d3ffdb9e395Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-0900000000-b4d0aef74055dd87486fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-c8884063706b25aca801Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-c8884063706b25aca801Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-0e190a36e93b266cb602Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-5900000000-2d12ae7fb469d0456cacSpectrum
Toxicity Profile
Route of ExposureOral (10) ; inhalation (10) ; dermal (10)
Mechanism of Toxicity4-Aminobiphenyl requires metabolic activation in order to exert its toxicity. This is catalyzed by N-hydroxylation via cytochrome P450 1A2, then followed by O-sulfation and O-acetylation by sulfotransferase 1A1 and arylamine N-acetyltransferase 2. The metabolites of 4-aminobiphenyl may form adducts with DNA, inducing mutations. 4-Aminobiphenyl and its metabolites may also cross the placenta and have fetal effects. (1, 2, 3, 4)
Metabolism4-Aminobiphenyl exposure can be assayed by measuring the extent of adduct formation with hemoglobin. 4-Aminobiphenyl metabolism is catalyzed by N-hydroxylation via cytochrome P450 1A2. It is then followed by O-sulfation and O-acetylation by sulfotransferase 1A1 and arylamine N-acetyltransferase 2. The urinary metabolites of 4-aminobiphenyl include 4-acetylaminobiphenyl, 4'-hydroxy-4-aminobiphenyl, 2'-hydroxy-4-acetylaminobiphenyl, 4'-hydroxy-4-acetylaminobiphenyl, 3'-hydroxy, 4'-methoxy-4-acetylaminobiphenyl, 4'-hydroxy, 3'-methoxy-4-acetylaminobiphenyl, and 3',4'-dihydroxy-4-acetylaminobiphenyl. (10, 4)
Toxicity ValuesLD50: 205 mg/kg (Oral, Mouse) (9)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (7)
Uses/Sources4-Aminobiphenyl is used to manufacture azo dyes and is also found in tobacco smoke. (8, 2)
Minimum Risk LevelNot Available
Health Effects4-Aminobiphenyl is a known human carcinogen. It may also cause methemoglobinemia. (7, 10)
SymptomsSymptoms of 4-aminobiphenyl may include dyspnea, headache, dizziness, lethargy, and ataxia. (10)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0013195
FooDB IDFDB029326
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link4-Aminobiphenyl
Chemspider ID6835
ChEBI ID1784
PubChem Compound ID7102
Kegg Compound IDC10998
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12778203
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15880493
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20433335
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=841184
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=8847111