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467278

Sigma-Aldrich

N-Methyl-o-toluidine

≥95%

Synonym(s):

2,N-Dimethylaniline, 2-Methyl-N-methylaniline, N,2-Dimethylaniline, N,2-Dimethylbenzenamine, N,o-Dimethylaniline, N-(2-Methylphenyl)methylamine, N-Methyl-2-methylaniline, N-Methyl-2-methylbenzenamine, N-Methyl-N-(o-tolyl)amine, N-Methyl-o-methylaniline, o,N-Dimethylaniline, Methyl(o-tolyl)amine, NSC 9395

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About This Item

Linear Formula:
CH3C6H4NHCH3
CAS Number:
611-21-2
Molecular Weight:
121.18
EC Number:
210-260-9
MDL number:
MFCD00025627
UNSPSC Code:
12352100
PubChem Substance ID:
24870394
NACRES:
NA.22

Assay

≥95%

bp

177-204 °C/740 mmHg (lit.)

density

0.981 g/mL at 25 °C (lit.)

SMILES string

CNc1ccccc1C

InChI

1S/C8H11N/c1-7-5-3-4-6-8(7)9-2/h3-6,9H,1-2H3

InChI key

GUAWMXYQZKVRCW-UHFFFAOYSA-N

General description

N-Methyl-o-toluidine can be synthesized by reacting o-toluidine and benzotriazole.

Application

N-Methyl-o-toluidine may be used in the preparation of 2-substituted N-methylindoles.
Reactant for:
  • Palladium-catalyzed coupling reactions
  • Palladium-catalyzed amination of bromoindazoles

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 3 - STOT RE 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

174.9 °F - closed cup

Flash Point(C)

79.4 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A Practical Synthetic Method for N-Methyl-o-Toluidine.
Katritzky AR and Akutagawa K.
Organic preparations and procedures international, 21(3), 340-341 (1989)
Jaakko Laakia et al.
Talanta, 132, 889-893 (2014-12-06)
Eight selected isomeric amines were ionized using atmospheric pressure chemical ionization and atmospheric pressure photoionization producing a protonated molecule [M+H](+) for each amine. The mobility of these ions was measured by ion mobility spectrometry. The amine compound class was shown
Carbon dioxide: a reagent for the simultaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack. XVI, A novel synthetic method for the side-chain functionalization of N-methyl-o-toluidine and for the preparation of 2-substituted N-methylindoles.
Katritzky AR, et al.
Heterocycles, 30(1), 407-414 (1990)

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