Record Information
Version1.0
Creation date2010-04-08 22:06:17 UTC
Update date2019-11-26 03:00:05 UTC
Primary IDFDB004550
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nameo-Toluidine
DescriptionO-toluidine, also known as 2-aminotoluene or 1-amino-2-methylbenzene, is a member of the class of compounds known as aminotoluenes. Aminotoluenes are organic aromatic compounds containing a benzene that carries a single methyl group and one amino group. O-toluidine is soluble (in water) and a strong basic compound (based on its pKa). O-toluidine can be found in tea, which makes O-toluidine a potential biomarker for the consumption of this food product. O-toluidine is formally rated as a carcinogenic (IARC 1) potentially toxic compound. The chemical properties of the toluidines are quite similar to those of aniline, and toluidines have properties in common with other aromatic amines. Due to the amino group bonded to the aromatic ring, the toluidines are weakly basic. The toluidines are poorly soluble in pure water but dissolve well in acidic water due to formation of ammonium salts, as usual for organic amines. ortho- and meta-toluidines are viscous liquids, but para-toluidine is a flaky solid. This difference is related to the fact that the p-toluidine molecules are more symmetrical. p-Toluidine can be obtained from reduction of p-nitrotoluene. p-Toluidine reacts with formaldehyde to form Tröger's base .
CAS Number95-53-4
Structure
Thumb
Synonyms
SynonymSource
1-Amino-2-methylbenzeneChEBI
1-Methyl-2-aminobenzeneChEBI
2-Amino-1-methylbenzeneChEBI
2-AminotolueneChEBI
2-Methyl-1-aminobenzeneChEBI
2-MethylbenzamineChEBI
2-MethylbenzenamineChEBI
2-ToluidineChEBI
O-AminotolueneChEBI
O-MethylanilineChEBI
O-MethylbenzenamineChEBI
O-TolylamineChEBI
2-Methyl-anilineHMDB
2-Methyl-benzenamineHMDB
2-MethylanilineHMDB, MeSH
2-Methylphenylamine (acd/name 4.0)HMDB
O-ToluideHMDB
O-ToluidinHMDB
O-Toluidine (acd/name 4.0)HMDB
O-ToluidynaHMDB
ortho-ToluidineHMDB, MeSH
Rcra waste number u328HMDB
2-Toluidine sulfateMeSH
2-Toluidine hydrochlorideMeSH
2-Toluidine perchlorateMeSH
2-Toluidine, (ar)-isomerMeSH
2-Toluidine, lithium saltMeSH
2-Methylaniline hydrochloridebiospider
Aniline, 2-methyl-biospider
Benzenamine, 2-methyl-biospider
O-aminotoluenebiospider
O-methylanilinebiospider
O-methylbenzenaminebiospider
O-toluidebiospider
O-toluidinbiospider
O-TOLUIDINE (SEE ALSO O-TOLUIDINE HYDROCHLORIDE 636-21-5)biospider
O-toluidine hydrochloridebiospider
o-Toluidine, liquid or solid [UN1708] [Poison]biospider
O-toluidynabiospider
O-tolylaminebiospider
Predicted Properties
PropertyValueSource
Water Solubility10.8 g/LALOGPS
logP1.32ALOGPS
logP1.66ChemAxon
logS-1ALOGPS
pKa (Strongest Basic)4.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.8 m³·mol⁻¹ChemAxon
Polarizability12.29 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H9N
IUPAC name2-methylaniline
InChI IdentifierInChI=1S/C7H9N/c1-6-4-2-3-5-7(6)8/h2-5H,8H2,1H3
InChI KeyRNVCVTLRINQCPJ-UHFFFAOYSA-N
Isomeric SMILESCC1=CC=CC=C1N
Average Molecular Weight107.1531
Monoisotopic Molecular Weight107.073499293
Classification
Description Belongs to the class of organic compounds known as aminotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and one amino group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassToluenes
Direct ParentAminotoluenes
Alternative Parents
Substituents
  • Aminotoluene
  • 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
Ontology
Physiological effect

Health effect:

Disposition

Source:

Role

Indirect biological role:

Biological role:

Environmental role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateliquid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point-16.3 oC
Boiling PointNot Available
Experimental Water Solubility16.6 mg/mL at 25 oCHUYSKENS,P et al. (1975)
Experimental logP1.32HANSCH,C ET AL. (1995)
Experimental pKa4.44
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-5900000000-f04208345695340d7d9fSpectrum
GC-MSo-Toluidine, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-ee7fe6869533a6858f94Spectrum
GC-MSo-Toluidine, non-derivatized, GC-MS Spectrumsplash10-0a4i-6900000000-68480e71423ffd272f9dSpectrum
GC-MSo-Toluidine, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-ee7fe6869533a6858f94Spectrum
GC-MSo-Toluidine, non-derivatized, GC-MS Spectrumsplash10-0a4i-6900000000-68480e71423ffd272f9dSpectrum
Predicted GC-MSo-Toluidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-7900000000-661d661a8df390a5081aSpectrum
Predicted GC-MSo-Toluidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-052f-9500000000-1da8fd338a6e499f67b8Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-e311b1811a6d3a59268aSpectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-1c57a6134b99aef82338Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-1843caa3f26f243817ebSpectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-e44d3c280fede3615b13Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-3cd853f6114cba521a13Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-b4d6fdb227e5b9621611Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-2900000000-2f6e21711a72ca0477a8Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4l-7900000000-c0f650fc70669757d0e6Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9400000000-bcd0a7b786b0217f655cSpectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9100000000-4312ff484c74be498895Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-4e34b2af3ed0df18b3b2Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0006-9000000000-8facfe25a950827aa822Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-00kf-9000000000-978c9096a7e167a13bc3Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-59dad1d5d1802381bc6aSpectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-31d6e4c02cb1c35d7e2dSpectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-ee83d5d19af792cc8783Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-4faf1f04148279e9331aSpectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0006-9000000000-4b5d5bc4707cf980910eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-a715018533d6dc4e8052Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-0370f837fa70b324ecfeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fc0-9000000000-f0196e420945b736f49bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-1000f1353d3e835b7498Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-3b8b19ef01e3a1cb8a0dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9800000000-aecf80c0988d8154d1e9Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID7242
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDO-TOLUIDINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).