Product Name
(Chloromethyl)Dimethylphenylsilane
Synonyms
chloromethyl-phenyldimethylsilane; dimethylphenylchloromethylsilane; (dimethylphenylsilyl)-methyl chloride; (Chloromethyl)dimethyl(phenyl)silane; PhMe2SiCH2Cl; Dichloromethyldimethylphenylsilane; Phenyldimethyl(chloromethyl)silane; Me2PhSiCH2Cl; ChloroMethyldiMethylphenylsilane; (Chloromethyl)dimethylphenylsilane; Silane,(chloromethyl)dimethylphenyl;
IUPAC Name
chloromethyl-dimethyl-phenylsilane
Molecular Weight
184.73 g/mol
Molecular Formula
C9H13ClSi
Boiling Point
223.8ºC at 760mmHg
Appearance
Transparent liquid
Application
(Chloromethyl)dimethylphenylsilane is primarily utilized as a versatile starting material in organic synthesis Initially reported in 1949 its main use was to convert into corresponding Grignard reagents Over time its applications have broadened to include heteroatom and carbon alkylation as well as the formation of various organometallic and organolanthanide reagents One of its distinct advantages over similar compounds like (chloromethyl)trimethylsilane is its capacity for Fleming oxidation which allows it to act as a masked hydroxyl group This property is especially useful for creating C- and N-substituted adducts However users must be cautious of its tendency to rearrange under certain conditions Additionally (chloromethyl)dimethylphenylsilane serves as a precursor for synthesizing (phenyldimethylsilyl)methoxymethyl chloride a hydroxyl protecting group known as SMOM-Cl It is effectively employed in the silylmethyl group installation on carbon through base-promoted C-alkylation working well with substrates like terminal alkynes dihydropyrazines malonic esters phenylacetonitriles sulfoxides and imines Occasionally conversion to its iodide form is preferred before alkylation These transformations typically require strong basic conditions and careful temperature control
Hazard Statements
Xi: Irritant;