Showing Compound o-Toluidine (FDB004550)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:17 UTC

Update date

2019-11-26 03:00:05 UTC

Primary ID

FDB004550

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

o-Toluidine

Description

O-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 Number

95-53-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1-Amino-2-methylbenzene	ChEBI
1-Methyl-2-aminobenzene	ChEBI
2-Amino-1-methylbenzene	ChEBI
2-Aminotoluene	ChEBI
2-Methyl-1-aminobenzene	ChEBI
2-Methylbenzamine	ChEBI
2-Methylbenzenamine	ChEBI
2-Toluidine	ChEBI
O-Aminotoluene	ChEBI
O-Methylaniline	ChEBI
O-Methylbenzenamine	ChEBI
O-Tolylamine	ChEBI
2-Methyl-aniline	HMDB
2-Methyl-benzenamine	HMDB
2-Methylaniline	HMDB, MeSH
2-Methylphenylamine (acd/name 4.0)	HMDB
O-Toluide	HMDB
O-Toluidin	HMDB
O-Toluidine (acd/name 4.0)	HMDB
O-Toluidyna	HMDB
ortho-Toluidine	HMDB, MeSH
Rcra waste number u328	HMDB
2-Toluidine sulfate	MeSH
2-Toluidine hydrochloride	MeSH
2-Toluidine perchlorate	MeSH
2-Toluidine, (ar)-isomer	MeSH
2-Toluidine, lithium salt	MeSH
2-Methylaniline hydrochloride	biospider
Aniline, 2-methyl-	biospider
Benzenamine, 2-methyl-	biospider
O-aminotoluene	biospider
O-methylaniline	biospider
O-methylbenzenamine	biospider
O-toluide	biospider
O-toluidin	biospider
O-TOLUIDINE (SEE ALSO O-TOLUIDINE HYDROCHLORIDE 636-21-5)	biospider
O-toluidine hydrochloride	biospider
o-Toluidine, liquid or solid [UN1708] [Poison]	biospider
O-toluidyna	biospider
O-tolylamine	biospider

Predicted Properties

Property	Value	Source
Water Solubility	10.8 g/L	ALOGPS
logP	1.32	ALOGPS
logP	1.66	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Basic)	4.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	35.8 m³·mol⁻¹	ChemAxon
Polarizability	12.29 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C7H9N

IUPAC name

2-methylaniline

InChI Identifier

InChI=1S/C7H9N/c1-6-4-2-3-5-7(6)8/h2-5H,8H2,1H3

InChI Key

RNVCVTLRINQCPJ-UHFFFAOYSA-N

Isomeric SMILES

CC1=CC=CC=C1N

Average Molecular Weight

107.1531

Monoisotopic Molecular Weight

107.073499293

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Toluenes

Direct Parent

Aminotoluenes

Alternative Parents

Substituents

Aminotoluene
Aniline or substituted anilines
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aminotoluene (CHEBI:66892 )

Ontology

Physiological effect

Health effect:

Health condition:

Cancer

Disposition

Source:

Environmental:

Tobacco smoke

Role

Indirect biological role:

Carcinogen

Biological role:

Nutrient

Environmental role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	liquid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	-16.3 oC
Boiling Point	Not Available
Experimental Water Solubility	16.6 mg/mL at 25 oC	HUYSKENS,P et al. (1975)
Experimental logP	1.32	HANSCH,C ET AL. (1995)
Experimental pKa	4.44
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-5900000000-f04208345695340d7d9f	Spectrum
GC-MS	o-Toluidine, non-derivatized, GC-MS Spectrum	splash10-0a4i-5900000000-ee7fe6869533a6858f94	Spectrum
GC-MS	o-Toluidine, non-derivatized, GC-MS Spectrum	splash10-0a4i-6900000000-68480e71423ffd272f9d	Spectrum
GC-MS	o-Toluidine, non-derivatized, GC-MS Spectrum	splash10-0a4i-5900000000-ee7fe6869533a6858f94	Spectrum
GC-MS	o-Toluidine, non-derivatized, GC-MS Spectrum	splash10-0a4i-6900000000-68480e71423ffd272f9d	Spectrum
Predicted GC-MS	o-Toluidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-7900000000-661d661a8df390a5081a	Spectrum
Predicted GC-MS	o-Toluidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-052f-9500000000-1da8fd338a6e499f67b8	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0006-9000000000-e311b1811a6d3a59268a	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0006-9000000000-1c57a6134b99aef82338	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0006-9000000000-1843caa3f26f243817eb	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0006-9000000000-e44d3c280fede3615b13	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-3cd853f6114cba521a13	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-0900000000-b4d6fdb227e5b9621611	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4i-2900000000-2f6e21711a72ca0477a8	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0a4l-7900000000-c0f650fc70669757d0e6	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0006-9400000000-bcd0a7b786b0217f655c	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0006-9100000000-4312ff484c74be498895	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0006-9000000000-4e34b2af3ed0df18b3b2	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0006-9000000000-8facfe25a950827aa822	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-00kf-9000000000-978c9096a7e167a13bc3	Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-0006-9000000000-59dad1d5d1802381bc6a	Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-0006-9000000000-31d6e4c02cb1c35d7e2d	Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-0006-9000000000-ee83d5d19af792cc8783	Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-0006-9000000000-4faf1f04148279e9331a	Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-0006-9000000000-4b5d5bc4707cf980910e	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-a715018533d6dc4e8052	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-0370f837fa70b324ecfe	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fc0-9000000000-f0196e420945b736f49b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-1000f1353d3e835b7498	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-3b8b19ef01e3a1cb8a0d	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9800000000-aecf80c0988d8154d1e9	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

7242

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

O-TOLUIDINE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Showing Compound o-Toluidine (FDB004550)

Structure for FDB004550 (o-Toluidine)