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409928

Sigma-Aldrich

N,N-Dimethyl-o-toluidine

99%

Synonym(s):

2,N,N-Trimethylaniline, 2-Methyl-N,N-dimethylaniline, N,N,2-Trimethylaniline, N,N,2-Trimethylbenzenamine, N,N-Dimethyl-2-methylaniline, N,N-Dimethyl-o-methylaniline, o-Methyl-N,N-dimethylaniline, o-Methyldimethylaniline

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About This Item

Linear Formula:
CH3C6H4N(CH3)2
CAS Number:
609-72-3
Molecular Weight:
135.21
EC Number:
210-199-8
MDL number:
MFCD00035789
UNSPSC Code:
12352100
PubChem Substance ID:
24865677
NACRES:
NA.22

Quality Level

200

Assay

99%

form

liquid

refractive index

n20/D 1.525 (lit.)

bp

76 °C/18 mmHg (lit.)

density

0.929 g/mL at 25 °C (lit.)

SMILES string

CN(C)c1ccccc1C

InChI

1S/C9H13N/c1-8-6-4-5-7-9(8)10(2)3/h4-7H,1-3H3

InChI key

JDEJGVSZUIJWBM-UHFFFAOYSA-N

Related Categories

General description

Complexing ability of N,N-dimethyl-o-toluidine with iodine has been evaluated. Influence of tetramethylethylenediamine on the lithiation of o- and p-N,N-dimethyl-o-toluidine has been studied.

Application

N,N-Dimethyl-o-toluidine may be employed as starting reagent for the synthesis of roseoflavin.

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

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(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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Effect of tetramethylethylenediamine on the metalation of o- and p-N,N-dimethyltoluidines with n-butyllithium. Deuteration and electrophilic condensation of intermediate lithioamines.
Ludt RE, et al.
The Journal of Organic Chemistry, 35(5), 1288-1296 (1970)
Molecular Complexes and Their Spectra. X. Molecular Complexes between Iodine and N, N-Dimethylaniline Derivatives.
Tsubomura H.
Journal of the American Chemical Society, 82(1), 40-45 (1960)
Photo-dynamics of roseoflavin and riboflavin in aqueous and organic solvents.
Zirak P, et al.
Chemical Physics, 358(1), 111-122 (2009)
Ségolène Villotte et al.
Molecules (Basel, Switzerland), 25(1) (2020-01-08)
Iodonium salts are well established photoacid generators, cationic photoinitiators, as well as additives commonly used in photoredox catalytic cycles. However, as a strong limitation, iodonium salts are characterized by low light absorption properties for λ > 300 nm so that

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