CAS 1833-51-8 (Chloromethyl)Dimethylphenylsilane

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(Chloromethyl)Dimethylphenylsilane

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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 serves multiple purposes in synthetic chemistry. Originally introduced in 1949, its primary use was as a precursor for the corresponding Grignard reagent. Over time, its applications expanded to encompass heteroatom and carbon alkylation, as well as conversion into diverse organometallic and organolanthanide reagents. Compared to its analogue, (chloromethyl)trimethylsilane, it holds the distinct advantage of undergoing Fleming oxidation, thereby functioning effectively as a masked hydroxyl group. This property is valuable for C-substituted and N-substituted adducts. However, it is important to consider its tendency to rearrange under varying conditions, which can limit its utility. A notable application of (chloromethyl)dimethylphenylsilane is as a precursor for (phenyldimethylsilyl)methoxymethyl chloride (SMOM-Cl), used as a hydroxyl protecting group. Furthermore, it can be employed to attach a silylmethyl group onto carbon through base-promoted C-alkylation, working with various substrates such as terminal alkynes and dihydropyrazines. While it can be used directly for alkylation, conversion to the iodide form via Finkelstein displacement may be desired under certain circumstances. Generally, except for reactions involving malonic esters, this transformation requires strong basic conditions and a meticulous temperature control regime.

Exact Mass

184.04800

Hazard Statements

Xi: Irritant;

Packaging

10 g; 100 g;

Safety Description

26-36

WGK Germany

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