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D145750

Sigma-Aldrich

N,N-Dimethylaniline

99%

Synonym(s):

N,N-Dimethylphenylamine, DMA, Dimethylaniline, Dimethylphenylamine

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About This Item

Linear Formula:
C6H5N(CH3)2
CAS Number:
121-69-7
Molecular Weight:
121.18
Beilstein:
507140
EC Number:
204-493-5
MDL number:
MFCD00008304
UNSPSC Code:
12352100
PubChem Substance ID:
329798700

Quality Level

100

Assay

99%

form

liquid

refractive index

n20/D 1.557 (lit.)

bp

193-194 °C (lit.)

mp

1.5-2.5 °C (lit.)

density

0.956 g/mL at 25 °C (lit.)

SMILES string

CN(C)c1ccccc1

InChI

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

InChI key

JLTDJTHDQAWBAV-UHFFFAOYSA-N

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General description

N,N-dimethylaniline (DMA) is N,N-disubstituted aniline. The thermo-physical and thermodynamic properties of the binary mixtures of DMA with anisole (ANS) and tert-butyl methyl ether (MTBE) have been reported. In acidic buffers it forms N,N,N′,N′-tetramethylbenzidine at a platinum electrode due anodic oxidation. DMA combines with diazonium salts to form methyl orange under alkaline condition. It forms ortho- and para-nitro derivatives via nitration reaction using N-bromosuccinimide/silver(I) nitrate reagent system in acetonitrile.

Application

N,N-dimethylaniline (DMA) may be used as a catalyst for reductive lithiation.
Reagent in new methodology for symmetrical and unsymmetrical photoconductor squaranes.

Legal Information

DuPont product

replaced by

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Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 2 - Carc. 2

WGK

WGK 3

Flash Point(F)

167.0 °F

Flash Point(C)

75 °C

Regulatory Information

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Fundamental Difference in Reductive Lithiations with Preformed Radical Anions versus Catalytic Aromatic Electron-Transfer Agents: N,N-Dimethylaniline as an Advantageous Catalyst.
Kennedy N, et al.
Angewandte Chemie (International Edition in English), 128(1), 391-394 (2016)
Aromatic nitration under neutral conditions using N-bromosuccinimide/silver (I) nitrate.
Nowrouzi N, et al.
Tetrahedron Letters, 53(36), 4841-4842 (2012)
Canadian Journal of Chemistry, 71, 494-494 (1993)
Anodic oxidation studies of N,N-dimethylaniline. I. Voltammetric and spectroscopic investigations at platinum electrodes.
Mizoguchi T and Adams RN.
Journal of the American Chemical Society, 84(11), 2058-2061 (1962)
Molecular interaction study through experimental and theoretical volumetric, acoustic and refractive properties of binary liquid mixtures at several temperatures 1. N,N-dimethylaniline with aryl, and alkyl ethers.
Master ZR and Malek NI.
Journal of Molecular Liquids, 196, 120-134 (2014)
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