Magnesium (phenyl)bromodichlorosilane (1.15 mL, 9.6 mmol) was added dropwise to a solution of dichlorodimethylsilane (5 mL) in Et₂O at 0 °C. The phenyl magnesium bromide was prepared from 4-bromobenzene (1.0 mL, 9.6 mmol) and magnesium powder particles (0.25 g, 10.6 mmol). The reaction mixture was brought to room temperature and stirred for 24 hours. After the reaction was complete, pentane was added to the reaction mixture. The precipitate was filtered off, and volatile substances were evaporated by rotary evaporation. The residue was purified by vacuum distillation (85 °C/6 mmHg) to obtain Chlorodimethylphenylsilane.
clear colorless to light yellow liquid
Chlorodimethylphenylsilane is used in the synthesis of enantioenriched allenylsilanes through an ortho-ester Claisen rearrangement of chiral and silylpropargylic alcohols.
Chlorodimethylphenylsilane can be used for nucleophilic silylation; alcohol derivatization; antenna chromophores; enolate capture; and Kumada-FlemingTamao oxidation.
Chlorodimethylphenylsilane is a combustible liquid, it can causes severe skin burns and eye damage.
Like other chlorosilanes, this compound can be destructive to tissue of the mucous membranes, upper respiratory tract, eyes and skin. Store in a cool dry place; the compound is moisture sensitive.
Fractionate it through a 1.5 x 18inch column packed with stainless steel helices, or a spinning band column. [Daudt & Hyde J Am Chem Soc 74 386 1952, Lewis et al. J Am Chem Soc 70 1115 1948, Eaborn J Chem Soc 494 1953.] It is used for standardising MeLi or MeMgBr which form Me3PhSi which is estimated by GC. [Maienthal et al. J Am Chem Soc 76 6392 1954, House & Respess J Organomet Chem 4 95 1965, Beilstein 16 IV 1475.] TOXIC and MOISTURE SENSITIVE.
