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T19526

Sigma-Aldrich

Tetramethylammonium chloride

reagent grade, ≥98%

Synonym(s):

TMA

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About This Item

Linear Formula:
(CH3)4N(Cl)
CAS Number:
75-57-0
Molecular Weight:
109.60
Beilstein/REAXYS Number:
3911201
EC Number:
200-880-8
MDL number:
MFCD00011628
UNSPSC Code:
12352100
PubChem Substance ID:
57654658
NACRES:
NA.21

grade

reagent grade

Quality Level

200

assay

≥98%

mp

>300 °C (lit.)

SMILES string

[Cl-].C[N+](C)(C)C

InChI

1S/C4H12N.ClH/c1-5(2,3)4;/h1-4H3;1H/q+1;/p-1

InChI key

OKIZCWYLBDKLSU-UHFFFAOYSA-M

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General description

Tetramethylammonium chloride is a quaternary ammonium salt commonly used as a catalyst due to its thermal stability and also tolerance towards strong aqueous bases or nucleophiles.

Application

Tetramethylammonium chloride along with N-hydroxyphthalimide and xanthone may be used as an efficient chloride catalytic system for the aerobic oxidation of hydrocarbons to form the corresponding oxygenated compounds. It may also be used as a phase transfer catalyst for the synthesis of aryl fluorides via selective chloride/fluoride exchange reaction of activated aryl chlorides with potassium fluoride in solid-liquid phase.

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Aquatic Chronic 2 - Skin Irrit. 2 - STOT SE 1 Oral

target_organs

Central nervous system

Storage Class

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

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW0078
MKCV2969
MKCT4602
MKCR3028
MKCQ0446

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A free radical process for oxidation of hydrocarbons promoted by nonmetal xanthone and tetramethylammonium chloride under mild conditions.
Du Z, et al.
Tetrahedron Letters, 50(15), 1677-1680 (2009)
Tetramethylammonium chloride as a selective and robust phase transfer catalyst in a solid?liquid halex reaction: the role of water.
Sasson Y, et al.
Chemical Communications (Cambridge, England), 3, 297-298 (1996)
Min Bum Park et al.
Journal of the American Chemical Society, 135(6), 2248-2255 (2012-11-29)
A solid understanding of the molecular-level mechanisms responsible for zeolite crystallization remains one of the most challenging issues in modern zeolite science. Here we investigated the formation pathway for high-silica LTA zeolite crystals in the simultaneous presence of tetraethylammonium (TEA(+))
Seonki Hong et al.
Science advances, 4(9), eaat7457-eaat7457 (2018-09-12)
Biological functions depend on biomolecular assembly processes. Assemblies of lipid bilayers, actins, microtubules, or chromosomes are indispensable for cellular functions. These hierarchical assembly processes are reasonably predictable by understanding chemical structures of the defined building blocks and their interactions. However
Markus Welcker et al.
Genes & development, 27(23), 2531-2536 (2013-12-04)
The Fbw7 tumor suppressor targets a broad network of proteins for ubiquitylation. Here we show critical functions for Fbw7 dimerization in regulating the specificity and robustness of degradation. Dimerization enables Fbw7 to target substrates through concerted binding to two suboptimal
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