Canmetcon
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Record Information
Version1.0
Creation Date2016-05-19 01:31:10 UTC
Update Date2016-11-09 01:09:15 UTC
Accession NumberCHEM003976
Identification
Common Name4-Aminoazobenzene
ClassSmall Molecule
DescriptionNot Available
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
4-(phenylazo)BenzenamineChEBI
4-(Phenyldiazenyl)anilineChEBI
4-AABChEBI
4-amino-1,1'-AzobenzeneChEBI
4-phenylazo-PhenylamineChEBI
4-PhenylazophenylamineChEBI
AABChEBI
Aniline yellowChEBI
P-AAZBChEBI
P-AminoazobenzeneChEBI
Chemical FormulaC12H11N3
Average Molecular Mass197.241 g/mol
Monoisotopic Mass197.095 g/mol
CAS Registry Number60-09-3
IUPAC Name4-[(E)-2-phenyldiazen-1-yl]aniline
Traditional Name4-aminoazobenzene
SMILESNC1=CC=C(C=C1)\N=N\C1=CC=CC=C1
InChI IdentifierInChI=1S/C12H11N3/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,13H2/b15-14+
InChI KeyQPQKUYVSJWQSDY-CCEZHUSRSA-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
  • Benzenoid
  • Monocyclic benzene moiety
  • Azo compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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 Solubility0.0295 mg/mLALOGPS
logP4.02ALOGPS
logP3.55ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)3.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.74 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.08 m3·mol-1ChemAxon
Polarizability21.91 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-9400000000-bddc382469003b252cc4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-9300000000-a745c70b5e39c99cfa4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-3900000000-9e32d1b72d3dd5cabee2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-9100000000-12cff3865d35f9f32f3bView in MoNA
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 IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAniline_Yellow
Chemspider ID5828
ChEBI ID233869
PubChem Compound IDNot Available
Kegg Compound IDC19187
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. http://www.ncbi.nlm.nih.gov/pubmed/?term=11084593
2. http://www.ncbi.nlm.nih.gov/pubmed/?term=13233869
3. http://www.ncbi.nlm.nih.gov/pubmed/?term=13243097
4. http://www.ncbi.nlm.nih.gov/pubmed/?term=14906551
5. http://www.ncbi.nlm.nih.gov/pubmed/?term=17899332
6. http://www.ncbi.nlm.nih.gov/pubmed/?term=18321769
7. http://www.ncbi.nlm.nih.gov/pubmed/?term=18844695
8. http://www.ncbi.nlm.nih.gov/pubmed/?term=23760354
9. http://www.ncbi.nlm.nih.gov/pubmed/?term=3607307
10. http://www.ncbi.nlm.nih.gov/pubmed/?term=6010711
11. http://www.ncbi.nlm.nih.gov/pubmed/?term=7265110
12. http://www.ncbi.nlm.nih.gov/pubmed/?term=8365123
13. TUNG TC, LIN JK (1964) THE INTERACTION OF NUCLEIC ACIDS WITH 4-DIMETHYL-AMINOAZOBENZENE AND 4-AMINOAZOBENZENE. [Tsa chih] [Journal of the] Alumni of the University of Takau. Gaoxiong yi xue yuan. Tong xue hui;Tsa Chih Gaoxiong Yi Xue Yuan Tong Xue Hui;1964 Apr;63:187-96 (PMID: 14198794)
14. TUNG TC, LIN JK (1964) THE INTERACTION OF RIBOFLAVIN WITH 4-DIMETHYLAMINOAZOBENZENE AND 4-AMINOAZOBENZENE. [Tsa chih] [Journal of the] Alumni of the University of Takau. Gaoxiong yi xue yuan. Tong xue hui;Tsa Chih Gaoxiong Yi Xue Yuan Tong Xue Hui;1964 May;63:225-32 (PMID: 14198351)
15. Hashimoto Y, Watanabe HK, Degawa M (1981) Mutagenicity of 4-aminoazobenzene, N-hydroxy-4-aminoazobenzene, 4-nitrosoazobenzene, 4-nitroazobenzene, and their ring methoxylated derivatives on Salmonella. Gann = Gan;Gann;1981 Dec;72(6):921-9 (PMID: 7042447)
16. Halasz I, Lukić K, Vancik H (2007) Hydrogen phosphate and dihydrogen phosphate salts of 4-aminoazobenzene. Acta crystallographica. Section C, Crystal structure communications;Acta Crystallogr C;2007 Jan;63(Pt 1):o61-4 (PMID: 17206059)
17. Watanabe HK, Hashimoto Y, Abe I, Sato H (1982) Carcinogenicities of 3-methoxy-4-aminoazobenzene, N-hydroxy-3-methoxy-4-aminoazobenzene and related azo dyes in the mouse. Gann = Gan;Gann;1982 Feb;73(1):136-40 (PMID: 7117744)
18. Kadlubar FF, Miller JA, Miller EC (1976) Microsomal N-oxidation of the hepatocarcinogen N-methyl-4-aminoazobenzene and the reactivity of N-hydroxy-N-methyl-4-aminoazobenzene. Cancer research;Cancer Res.;1976 Mar;36(3):1196-1206 (PMID: 814998)
19. Lin JK, Sung SS (1975) Comparative studies on the carcinogenecities of N, N-dimethyl-4-aminoazobenzene and N'-acetyl-N'-methyl-4'-amino-N, N-dimethyl-4-aminoazobenzene in a normal diet. Taiwan yi xue hui za zhi. Journal of the Formosan Medical Association;Taiwan Yi Xue Hui Za Zhi;1975 Aug;74(8):534-40 (PMID: 816989)
20. Fujii K (1983) Induction of tumors in transplacental or neonatal mice administered 3'-methyl-4-dimethylaminoazobenzene or 4-aminoazobenzene. Cancer letters;Cancer Lett.;1983 Jan;17(3):321-5 (PMID: 6403219)
21. Liu Y, Zhao YL, Chen Y, Guo DS (2005) Assembly behavior of inclusion complexes of beta-cyclodextrin with 4-hydroxyazobenzene and 4-aminoazobenzene. Organic & biomolecular chemistry;Org. Biomol. Chem.;2005 Feb;3(4):584-91 (PMID: 15703792)
22. Naimy NK, Namkung MJ, Flther TL (1969) Thin-layer chromatography of fluorinated 4-aminoazobenzene and its N-methylated and 4'-ethyl derivatives. Journal of chromatography;J. Chromatogr.;1969 Sep;43(4):537-8 (PMID: 5811003)