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Merck
CN

386529

Chlorotrimethylsilane

purified by redistillation, ≥99%

Synonym(s):

TMSCl, TMCS, Trimethylchlorosilane, Trimethylsilyl chloride

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About This Item

Linear Formula:
(CH3)3SiCl
CAS Number:
75-77-4
Molecular Weight:
108.64
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
24864097
EC Number:
200-900-5
Beilstein/REAXYS Number:
1209232
MDL number:
MFCD00000502

Key Documents

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Product Name

Chlorotrimethylsilane, purified by redistillation, ≥99%

InChI key

IJOOHPMOJXWVHK-UHFFFAOYSA-N

InChI

1S/C3H9ClSi/c1-5(2,3)4/h1-3H3

SMILES string

C[Si](C)(C)Cl

vapor density

3.7 (vs air)

vapor pressure

100 mmHg ( 25 °C)

assay

≥99%

form

liquid

autoignition temp.

752 °F

purified by

glass distillation
redistillation

expl. lim.

6.4 %

impurities

<0.1% dichlorodimethylsilane

refractive index

n20/D 1.387 (lit.)

bp

57 °C (lit.)

mp

−40 °C (lit.)

density

0.856 g/mL at 25 °C (lit.)

Quality Level

200

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Application

Chlorotrimethylsilane (TMSCl) can be used as:       
  • A reagent to protect alcohol and amine groups via the formation of trimethylsilyl ethers and trimethylsilyl amines.      
  • A catalyst for the preparation of 1,3-diphenyl-2-propenone derivatives (chalcones) as antimicrobial agents.        
  • A trapping agent for the anions generated during acyloin condensation reaction.       
  • A better alternative catalyst to the toxic mercuric chloride for the activation of samarium (Sm) during the cyclopropanation of both allylic and α-allenic alcohols.
  •  A catalyst in the transesterification of triglycerides with alcohols to form fatty acid alkyl esters.        
  • A reagent along with lithium bromide for the conversion of alcohols to the corresponding bromides.       
  • A reagent in Fischer glycosidation.       
  • A source of acid catalyst in the reductive benzylation reaction using benzaldehyde and Et3SiH.
  • A reagent to synthesize sodium trimethylsilanethiolate (Me3SiSNa) by reacting with sodium sulfide, which is an odorless alternative method of synthesizing Me3SiSNa from foul-smelling bis(trimethylsilyl)sulfide and sodium methoxide.

General description

Chlorotrimethylsilane is a chloroorganosilane compound mainly used for silylation reactions.

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Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1A

supp_hazards

EUH014

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

-18.4 °F - closed cup

flash_point_c

-28 °C - closed cup

ppe

Faceshields, Gloves, Goggles

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SHBT3527
SHBT3526
BCCN9259
SHBS5421
SHBS5420

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Acyloin Condensation in which Chlorotrimethylsilane is used as a Trapping Agent: 1, 2-Bis (trimethylsilyloxy) cyclobutene and 2-Hydroxycyclobutanone: Trimethylsilane, 1-cyclobuten-1, 2-ylenedioxybis-and Cyclobutanone, 2-hydroxy-
Bloomfield JJ and Nelke JM
Organic Syntheses, 57, 1-1 (2003)
TMSCl as a mild and effective source of acidic catalysis in Fischer glycosidation and use of propargyl glycoside for anomeric protection
Izumi M, et al.
Bioscience, Biotechnology, and Biochemistry, 66(1), 211-214 (2002)
Jukun Xiong et al.
Environmental pollution (Barking, Essex : 1987), 219, 596-603 (2016-06-29)
To reveal the emission patterns of brominated flame retardants (BFRs) in the Beijiang River, South China, concentrations of polybrominated diphenyl ethers (PBDEs) and phenolic BFRs (2,4,6-tribromophenol (TBP), pentabromophenol (PeBP), tetrabromobisphenol A (TBBPA)), and bisphenol A (BPA) in water and sediments
Potassium dodecatangestocobaltate trihydrate (K5CoW12O40{\textperiodcentered} 3H2O): a mild and efficient catalyst for deprotection of dioxolanes and trimethylsilyl ethers
Habibi MH, et al.
Tetrahedron Letters, 42(38), 6771-6774 (2001)
Guozhong Zhao et al.
Frontiers in microbiology, 11, 579808-579808 (2021-01-26)
Japanese soy sauce has become more acceptable by Chinese consumers due to its umami taste. However, the volatile flavor compounds and taste characters have not been fully clarified. This study aimed to explore the flavor characteristics of three kinds of
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