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386529

Sigma-Aldrich

Chlorotrimethylsilane

purified by redistillation, ≥99%

Synonym(s):
Trimethylsilyl chloride, TMSCl, TMCS, Trimethylchlorosilane
Linear Formula:
(CH3)3SiCl
CAS Number:
Molecular Weight:
108.64
Beilstein:
1209232
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

vapor density

3.7 (vs air)

vapor pressure

100 mmHg ( 25 °C)

assay

≥99%

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.

Packaging

1, 2 L in Sure/Seal™
25, 100, 4×100 mL in Sure/Seal™

signalword

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

Storage Class Code

3 - Flammable liquids

WGK Germany

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

Certificate of Analysis

Certificate of Origin

Lijie Zhou et al.
Polymers, 11(4) (2019-04-21)
Under the current situation of frequent oil spills, the development of green and recyclable high-efficiency oil-absorbing aerogel materials has attracted wide attention from researchers. In this study, we report a high-strength, three-dimensional hydrophobic cellulose nanofiber (CNF)/polyvinyl alcohol (PVA)/graphene oxide (GO)...
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)
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)
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)
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...

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