ChemFOnt: Showing chemical card for o-Toluidine (CFc000333544)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:44 UTC

Chemfont ID

CFc000333544

Molecule Identification

Common Name

o-Toluidine

Definition

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 .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	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

Chemical Formula

C₇H₉N

Average Molecular Weight

107.1531

Monoisotopic Molecular Weight

107.073499293

IUPAC Name

2-methylaniline

Traditional Name

toluidine

CAS Registry Number

95-53-4

SMILES

CC1=CC=CC=C1N

InChI Identifier

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

InChI Key

RNVCVTLRINQCPJ-UHFFFAOYSA-N

Chemical Taxonomy

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 )

Functional Ontology

Physiological effect

Health effect

Cancer

Cancer (HMDB: HMDB0041965)

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0041965)
Extracellular (HMDB: HMDB0041965)

Source

Exogenous

Exogenous (HMDB: HMDB0041965)

Environmental

Tobacco Smoke (HMDB: HMDB0041965)

Not Available

Indirect biological role

Carcinogen (HMDB: HMDB0041965)

Environmental role

Air pollutant (HMDB: HMDB0041965)

Biological role

Carcinogenic agent (HMDB: HMDB0041965)
Nutrient (HMDB: HMDB0041965)

Physical Properties

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