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386529

Sigma-Aldrich

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
Beilstein:
1209232
EC Number:
200-900-5
MDL number:
MFCD00000502
UNSPSC Code:
12352302
PubChem Substance ID:
24864097
NACRES:
NA.22

vapor density

3.7 (vs air)

Quality Level

200

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.)

SMILES string

C[Si](C)(C)Cl

InChI

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

InChI key

IJOOHPMOJXWVHK-UHFFFAOYSA-N

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General description

Chlorotrimethylsilane is a chloroorganosilane compound mainly used for silylation reactions.

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.

Signal Word

Danger

Hazard Classifications

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

Supplementary Hazards

EUH014

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

-18.4 °F - closed cup

Flash Point(C)

-28 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chlorotrimethylsilane in combination with sodium sulfide as the equivalent of sodium trimethylsilanethiolate in organic reactions.
Shiao M
The Journal of Organic Chemistry, 58(17), 4742-4744 (1993)
Houben-Weyl Methods of Molecular Transformations Vol. 4: Compounds of Groups 15 (As, Sb, Bi) and Silicon Compounds
Sci. Synth., 261-261 (2014)
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
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)
Chlorotrimethylsilane as a mild and effective source of acid catalyst in reductive benzylation
Izumi M and Fukase K
Chemistry Letters (Jpn), 34(4), 594-595 (2005)
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