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Merck

D189006

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24893566
EC Number:
202-805-4
Beilstein/REAXYS Number:
774409
MDL number:
MFCD00008316
Assay:
99%
Form:
liquid

Key Documents

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InChI key

GYVGXEWAOAAJEU-UHFFFAOYSA-N

InChI

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

SMILES string

CN(C)c1ccc(C)cc1

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.)

Quality Level

200

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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

target_organs

Respiratory Tract,Blood

Storage Class

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

flash_point_f

168.8 °F - closed cup

flash_point_c

76 °C - closed cup

ppe

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

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Acute Tox. 4 Inhalation - Aquatic Chronic 3 - Carc. 1B - Repr. 2 - Skin Sens. 1 - STOT RE 2

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Certificates of Analysis (COA)

Lot/Batch Number
MKDB0466
MKCZ8048
MKCZ1599
MKCX3268
MKCX2827

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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
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
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).
Richard Milner
Journal of biomedical materials research. Part B, Applied biomaterials, 68(2), 180-185 (2004-01-23)
Commercially available acrylic bone cements are two-component systems based on the polymerization of methyl methacrylate around poly(methyl methacrylate) particles. When benzoyl peroxide (BPO), which is the initiator, in the powder component meets accelerator (N,N-dimethyl-p-toluidine (DMpT)) in the liquid component, radicals
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