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D189006

Sigma-Aldrich

4,N,N-Trimethylaniline

99%

Synonym(s):

4-Dimethylaminotoluene, N,N-Dimethyl-p-toluidine

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About This Item

Linear Formula:
CH3C6H4N(CH3)2
CAS Number:
Molecular Weight:
135.21
Beilstein/REAXYS Number:
774409
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor density

>1 (vs air)

assay

99%

form

liquid

expl. lim.

7 %

refractive index

n20/D 1.546 (lit.)

bp

211 °C (lit.)
90-92 °C/10 mmHg (lit.)

density

0.937 g/mL at 25 °C (lit.)

SMILES string

CN(C)c1ccc(C)cc1

InChI

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

InChI key

GYVGXEWAOAAJEU-UHFFFAOYSA-N

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Application

4,N,N-Trimethylaniline is a tertiary amine that can undergo iron-catalyzed oxidative C-C coupling with phenylacetylene and benzamide in the presence of tert-butylperoxide to form N,4-dimethyl-N-(3-phenylprop-2-ynyl)benzenamine and N-((methyl(p-tolyl)amino)methyl)benzamide, respectively.

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Aquatic Chronic 3 - Carc. 1B - Repr. 2 - Skin Sens. 1 - STOT RE 2 Oral

target_organs

Reproductive organs

Storage Class

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

wgk_germany

WGK 3

flash_point_f

168.8 °F - closed cup

flash_point_c

76 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


Certificates of Analysis (COA)

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Chemoselective C? H Bond Activation: Ligand and Solvent Free Iron-Catalyzed Oxidative C? C Cross-Coupling of Tertiary Amines with Terminal Alkynes. Reaction Scope and Mechanism.
Volla C M R, et al.
Organic Letters, 11(8), 1701-1704 (2009)
M Noda et al.
Journal of biomedical materials research. Part A, 83(1), 123-129 (2007-03-27)
Resin composites are widely used in dentistry, and are polymerized in situ using a blue-light activated, free-radical polymerization mechanism. Blue light (400-500nm) is used to activate camphoroquinone (CQ), which decomposes to form free radicals that are stabilized by dimethyl-p-toludine (DMPT).
Jennifer L Moreau et al.
Journal of biomedical materials research. Part A, 81(3), 594-602 (2006-12-21)
There is an increasing need to develop new biomaterials as tissue engineering scaffolds. Unfortunately, many of the materials that have been studied for these purposes are polyesters that hydrolytically degrade into acidic products, which may harm the surrounding tissue, and
S Makihira et al.
Mycoses, 45(8), 300-305 (2003-02-08)
The effects of four liquid components of denture acrylic resin on host cell activity and fungal adhesion were investigated in this study. The low concentration (1 micromol l(-1)) of the liquid components caused no change in the activities and morphologies
Y Nomura et al.
Journal of materials science. Materials in medicine, 17(1), 29-32 (2006-01-04)
The polymerization initiators for resins cured using visible light usually consist of a photosensitizer, primarily camphorquinone (CQ), and a reducing agent, which is often a tertiary amine (DMPT, DMAEMA), while the initiator used for self-curing resins consists of benzoyl peroxide

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