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Sigma-Aldrich

4,N,N-Trimethylaniline

catalyst grade (for peroxide polymerization), ≥98.5% (GC)

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Synonym(s):
4-Dimethylaminotoluene, N,N-Dimethyl-p-toluidine
Linear Formula:
CH3C6H4N(CH3)2
CAS Number:
99-97-8
Molecular Weight:
135.21
Beilstein:
774409
EC Number:
202-805-4
MDL number:
MFCD00008316
PubChem Substance ID:
57650079
NACRES:
NA.22

grade

catalyst grade (for peroxide polymerization)

Quality Level

200

vapor density

>1 (vs air)

Assay

≥98.5% (GC)

form

liquid

expl. lim.

7 %

refractive index

n20/D 1.546 (lit.)
n20/D 1.547

bp

211 °C (lit.)
90-92 °C/10 mmHg (lit.)

density

0.936 g/mL at 20 °C
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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General description

4,N,N-Trimethylaniline is a N-methyl-N-alkylaniline. Its reaction with vinyl ether catalyzed by CuCl2 has been reported to afford tetrahydroquinolines. Its radical cation undergoes reaction with the anthracene radical anion and generation of electrogenerated chemiluminescence (ECL) has been observed.

Caution

may discolor to yellowish-green on storage

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Aquatic Chronic 3 - STOT RE 2 Oral

Target Organs

Reproductive organs

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

168.8 °F - closed cup

Flash Point(C)

76 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Xianghua Yang et al.
Molecules (Basel, Switzerland), 11(12), 978-987 (2007-11-17)
Tetrahydroquinoline skeletons can be formed by a CuCl2-catalyzed one-pot reaction of N-methyl-N-alkylanilines and vinyl ethers in the presence of t-butyl-hydroperoxide.
Jacob B Ketter et al.
Journal of the American Chemical Society, 126(32), 10183-10189 (2004-08-12)
Electrogenerated chemiluminescence (ECL) arising from the reaction of radical ions has previously be shown to arise from a variety of states including excited singlets, triplets, excimers, and exciplexes. In this work we describe two systems that form emissive states in
Julie M Hasenwinkel et al.
Journal of biomedical materials research, 59(3), 411-421 (2002-01-05)
Porous-free, two-solution bone cements have been developed in our laboratory as an alternative to commercial powder/liquid formulations. Each pair of solutions consist of poly(methyl methacrylate) (PMMA) powder dissolved in methyl methacrylate (MMA) monomer, with benzoyl peroxide (BPO) added to one
Kouhei Masuki et al.
Dental materials journal, 26(6), 861-869 (2008-01-22)
The aim of this study was to examine the apoptotic and necrotic influence of four dental resin polymerization initiators--namely benzoyl peroxide (BPO), camphorquinone (CQ), dimethylaminoethyl methacrylate (DMAEMA), and dimethyl-para-toluidine (DMPT)--on human gingival fibroblast (HGF) cells. To this end, the growth
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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