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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.)

functional group

amine

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.[1]

Application

N-Methyl-o-toluidine may be used in the preparation of 2-substituted N-methylindoles.[2]
Dye intermediate
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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

467278-100ML:4548173155425
467278-VAR:
467278-BULK:
467278-25ML:4548173155432

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Certificates of Analysis (COA)

Lot/Batch Number
BGBB7387
BGBB7460
21712JA
18722HO
01109TA

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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)
A Practical Synthetic Method for N-Methyl-o-Toluidine.
Katritzky AR and Akutagawa K.
Organic preparations and procedures international, 21(3), 340-341 (1989)

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