BIS(TRIMETHYLSILYL)CHLOROMETHANE

Physical properties

bp 57–60°C(15 mmHg); flash point 48 °C; d 0.892 gmL?1 (25 °C).

Uses

Silane, 1,1
-(Chloromethylene)bis[1,1,1]- trimethyl- can be used as versatile C1 building block; broad application in Peterson olefination reactions; Grignard reagent participates readily in Kumada cross-coupling reactions with aryl and vinyl halides; useful in synthesis of methylenephosphine analogs and as sterically demanding ligand for a number of main group and transition metal complexes.

Uses

Chlorobis(trimethylsilyl)methane can be used as a reagent for the preparation of:

• Para-bis(trimethylsilyl)ethylstyrene (PBTES) monomer, which is used to synthesize corresponding network polymer of styrene.
• Bis(trimethylsilyl)methyl magnesium chloride (Grignard reagent), which is used in the synthesis of bis(trimethylsilyl) allyl compounds by reacting with alkenyl bromide via the Kumada coupling reaction.
• N-[Bis(trimethylsilyl)methyl]heterocumulenes.

Preparation

a convenient one-pot procedure has been developed by Kemp and Cowley in which trimethylsilylchloride reacts with dichloromethane in the presence of nBuLi at ?110°Cto give bis(trimethylsilyl)dichloromethane.1 This intermediate is sequentially treated with nBuLi and ethanol to yield chlorobis(trimethylsilyl)methane. A number of other syntheses have been described