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Record Information
Version1.0
Creation Date2016-05-19 01:31:11 UTC
Update Date2016-11-09 01:09:15 UTC
Accession NumberCHEM003977
Identification
Common Name4-Dimethylaminoazobenzene
ClassSmall Molecule
DescriptionNot Available
Contaminant Sources
  • Clean Air Act Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
N,N-Dimethyl-4-(phenylazo)benzenamineKegg
Dimethyl yellowKegg
Methyl yellowKegg
4-(dimethylamino)PhenylazobenzeneKegg
Chemical FormulaC14H15N3
Average Molecular Mass225.295 g/mol
Monoisotopic Mass225.127 g/mol
CAS Registry Number60-11-7
IUPAC NameN,N-dimethyl-4-[(E)-2-phenyldiazen-1-yl]aniline
Traditional Namedimethylaminoazobenzene
SMILESCN(C)C1=CC=C(C=C1)\N=N\C1=CC=CC=C1
InChI IdentifierInChI=1S/C14H15N3/c1-17(2)14-10-8-13(9-11-14)16-15-12-6-4-3-5-7-12/h3-11H,1-2H3/b16-15+
InChI KeyJCYPECIVGRXBMO-FOCLMDBBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzobenzenes
Sub ClassNot Available
Direct ParentAzobenzenes
Alternative Parents
Substituents
  • Azobenzene
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary amine
  • Azo compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0383 mg/mLALOGPS
logP4.63ALOGPS
logP4.49ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)3.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.96 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.81 m3·mol-1ChemAxon
Polarizability26.2 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID4-DIMETHYLAMINOPHENYLAZOBENZENE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID5829
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDC03764
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. (2002) 4-Dimethylaminoazobenzene. Report on carcinogens : carcinogen profiles / U.S. Dept. of Health and Human Services, Public Health Service, National Toxicology Program;Rep Carcinog;2002 ;10:103 (PMID: 15323046)
2. (2004) 4-Dimethylaminoazobenzene. Report on carcinogens : carcinogen profiles / U.S. Dept. of Health and Human Services, Public Health Service, National Toxicology Program;Rep Carcinog;2004 ;11:III103-4 (PMID: 21089865)
3. (2011) 4‑Dimethylaminoazobenzene. Report on carcinogens : carcinogen profiles / U.S. Dept. of Health and Human Services, Public Health Service, National Toxicology Program;Rep Carcinog;2011 ;12:167-8 (PMID: 21852828)
4. HECHT G (1952) The effects of dimethylaminoazobenzene. Naunyn-Schmiedebergs Archiv für experimentelle Pathologie und Pharmakologie;Naunyn Schmiedebergs Arch Exp Pathol Pharmakol;1952 ;215(5-6):610-8 (PMID: 12977253)
5. ROBINSON PJ, RYAN AJ, WRIGHT SE (1964) METABOLISM OF SOME DIMETHYLAMINOAZOBENZENE DERIVATIVES. The Journal of pharmacy and pharmacology;J. Pharm. Pharmacol.;1964 Dec;16:SUPPL:80-2T (PMID: 14265946)
6. ISHIDATE M, TAMURA Z, NAKAJIMA T, SAMEJIMA K (1962) Metabolites of p-dimethylaminoazobenzene in rat bile. Chemical & pharmaceutical bulletin;Chem. Pharm. Bull.;1962 Jan;10:75-6 (PMID: 13956819)
7. FONES WS, WHITE J (1949) Preparation of p-dimethylaminoazobenzene containing isotopic nitrogen. Archives of biochemistry;Arch Biochem;1949 Jan;20(1):118-24 (PMID: 18104402)
8. Suzuki H, Komatsu K, Imamura T, Miyazaki A, Kobayashi T, Nomura M (2006) Genotoxicity studies OF p-dimethylaminoazobenzene (DAB). The Journal of toxicological sciences;J Toxicol Sci;2006 Oct;31(4):399-405 (PMID: 17077593)
9. HARRIS PN, CLOWES GH (1952) Observations on carcinogenesis by 4-dimethylaminoazobenzene. Cancer research;Cancer Res.;1952 Jul;12(7):471-9 (PMID: 14936017)
10. KOLTHOFF IM, JOHNSON WF (1946) Solubilization of p-dimethylaminoazobenzene in soap solutions. The Journal of physical chemistry;J Phys Chem;1946 Sep;50(5):440-2 (PMID: 20281662)