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  • (Chloromethyl)Dimethylphenylsilane

  • (Chloromethyl)Dimethylphenylsilane

    Catalog Number
    ACM1833518
    CAS Number
    1833-51-8
    Product Name
    (Chloromethyl)Dimethylphenylsilane
    Structure
    Category
    Salt
    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
    Flash Point
    91.1ºC
    Purity
    95%+
    Density
    0.99g/cm³
    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
    Exact Mass
    184.04800
    Hazard Statements
    Xi: Irritant;
    Packaging
    10 g; 100 g;
    Safety Description
    26-36
    WGK Germany
    3
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