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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)
Sachiko Kaihara et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 68(1), 67-73 (2007-09-25)
While many synthetic, hydrolytically degradable hydrogels have been developed for biomedical applications, there are only a few examples whose polymer backbone does not form acidic products upon degradation. In order to address this concern, we proposed to develop a hydrogel
Kyle Winter et al.
Biomaterials, 26(26), 5321-5329 (2005-04-09)
Previous investigations have found that visible-light (VL)-irradiated camphorquinone (CQ), in the presence of a tertiary amine (e.g., N,N-dimethyl-p-toluidine, DMT), generates reactive oxygen species and causes oxidative DNA damage in vitro. In this study, oxidative DNA damage produced by VL-irradiated CQ/DMT
Anuradha Prakki et al.
Dental materials : official publication of the Academy of Dental Materials, 25(1), 26-32 (2008-09-02)
The purpose of this study was to evaluate the effect of two additives, propionaldehyde/aldehyde or 2,3-butanedione/diketone, on mechanical properties of Bis-GMA-based composites containing TEGDMA, propoxylated Bis-GMA (CH(3)Bis-GMA) or propoxylated fluorinated Bis-GMA (CF(3)Bis-GMA). Three control composites, Bis-GMA/diluent monomer (25/75 mol%), and
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
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