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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:
99-97-8
Molecular Weight:
135.21
Beilstein/REAXYS Number:
774409
EC Number:
202-805-4
MDL number:
MFCD00008316
UNSPSC Code:
12352100
PubChem Substance ID:
24893566
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
GHS06,GHS08

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)
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
Yi-Ching Li et al.
Journal of biomedical materials research. Part B, Applied biomaterials, 84(1), 58-63 (2007-04-25)
9-Fluorenone (9F), the aromatic photosensitizer, is widely used as an initiator in visible-light (VL) cured resin systems. There is growing concern that 9F may produce genetic damage by inducing mutation. In this study, 9F in the presence or absence of
Chiemi Hirabayashi et al.
Dental materials journal, 21(4), 314-321 (2003-03-01)
Polymerization characteristics of poly (methyl methacrylate)(PMMA)/(methyl methacrylate) (MMA) resin initiated by tributylborane (TBB) were compared with those by benzoyl peroxide (BPO)/N,N-dimethyl-p-toluidine and camphorquinone (CQ)/N,N-dimethylaminoethyl methacrylate from the aspects of temporal changes of residual MMA and molecular weight up to 4
Yi-Ching Li et al.
Journal of biomedical materials research. Part B, Applied biomaterials, 82(1), 23-28 (2006-10-17)
Camphorquinone (CQ) is widely used as an initiator in modern visible-light (VL) cured resin systems. CQ is also characterized as a potential allergenic compound. To date, there is growing concern that CQ may produce genetic damage by inducing mutation. In
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