386529

Chlorotrimethylsilane

purified by redistillation, ≥99%

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

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS02,GHS06,GHS05
• signalword: Danger
• hcodes: H225,H301 + H331,H312,H314
• pcodes: P210 - P233 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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
• wgk_germany: WGK 1
• ppe: Faceshields, Gloves, Goggles