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41690

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
UNSPSC Code:
12352100
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.

Application

  • Charge-transfer complexes for redox polymerization: 4,N,N-Trimethylaniline used for on-demand amine/peroxide redox polymerization. This research offers a new perspective on the use of 4,N,N-Trimethylaniline in creating controlled polymer structures, which is crucial for various industrial and pharmaceutical applications (Garra et al., 2018).

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 - Carc. 1B - Repr. 2 - Skin Sens. 1 - STOT RE 2 Oral

Target Organs

Reproductive organs

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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
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.
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
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