(Chloromethyl)dimethylphenylsilane

[1833-51-8] C9H13ClSi (MW 184.74) InChI = 1S/C9H13ClSi/c1-11(2,8-10)9-6-4-3-5-7-9/h3-7H,8H2,1-2H3 InChIKey = RJCTVFQQNCNBHG-UHFFFAOYSA-N (masked hydroxyl group,7, 8, 11, 26-31 preparation of SMOM-Cl,4 C-alkylating agent,5-10 N-alkylating agent,12-17 O-alkylating agent,18, 19, 21, 22 S-alkylating agent,23 preparation of Grignard reagents,27-33 alkene formation,28e,35 preparation of organolithium reagents40-45) Alternate names: [(chloromethyl)dimethylsilyl]benzene; chloromethylphenyldimethylsilane; dimethylphenylsilylmethyl chloride; phenyldimethyl(chloromethyl)silane. Physical data: bp 106–107 °C/15 mmHg; d 1.024 g cm−3 Preparative Methods: can be prepared either by the reaction of phenylmagnesium bromide with chloro(chloromethyl)dimethylsilane in ether at reflux,1 or by the reaction of phenylmagnesium bromide with chloro(chloromethyl)dimethylsilane in the presence of catalytic (N,N,N′,N′-tetramethylethylenediamine)zinc in 1,4-dioxane at 20 °C.2 Purification: for most applications, the material may be used as received. For applications requiring rigorous exclusion of impurities and oxygen, the material may be further purified by stirring with phosphorus pentoxide followed by distillation. Handling, Storage, and Precautions: reagent is stable to normal temperatures and pressures. Causes skin irritation and serious eye irritation. May cause respiratory irritation. Wear suitable personal protective equipment and use in a fume hood.