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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

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

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 1

Flash Point(F)

145.4 °F - closed cup

Flash Point(C)

63 °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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Photo-dynamics of roseoflavin and riboflavin in aqueous and organic solvents.
Zirak P, et al.
Chemical Physics, 358(1), 111-122 (2009)
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)
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)
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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