CHLOROMETHYLDIMETHYLPHENYLSILANE

CHLOROMETHYLDIMETHYLPHENYLSILANE Basic information
Product Name:CHLOROMETHYLDIMETHYLPHENYLSILANE
Synonyms:(chloromethyl)dimethylphenyl-silan;Dichloromethyldimethylphenylsilane;Phenyldimethyl(chloromethyl)silane;CHLOROMETHYLDIMETHYLPHENYLSILANE;Silane, (chloromethyl)dimethylphenyl-;Dimethylphenylsilyldichloromethane;Chloromethylphenyldimethylsilane;Phenyl(chloromethyl)dimethylsilane
CAS:1833-51-8
MF:C9H13ClSi
MW:184.74
EINECS:217-392-6
Product Categories:Chemical Synthesis;Organometallic Reagents;Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Organometallic Reagents;Organosilicon;Others
Mol File:1833-51-8.mol
CHLOROMETHYLDIMETHYLPHENYLSILANE Structure
CHLOROMETHYLDIMETHYLPHENYLSILANE Chemical Properties
Boiling point 106-107 °C/15 mmHg (lit.)
density 1.024 g/mL at 25 °C (lit.)
refractive index n20/D 1.520(lit.)
Fp 196 °F
storage temp. 2-8°C
form clear liquid
color Colorless to Almost colorless
Specific Gravity1.031
Hydrolytic Sensitivity4: no reaction with water under neutral conditions
BRN 2935991
CAS DataBase Reference1833-51-8(CAS DataBase Reference)
EPA Substance Registry SystemSilane, (chloromethyl)dimethylphenyl- (1833-51-8)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-26/36
RIDADR 1993
WGK Germany 3
TSCA Yes
HS Code 29319000
MSDS Information
ProviderLanguage
SigmaAldrich English
CHLOROMETHYLDIMETHYLPHENYLSILANE Usage And Synthesis
Physical propertiesbp 106–107°C/15 mmHg; d 1.024 g cm?3
UsesThe first reported preparation and use of (chloromethyl)dimethylphenylsilane was in 1949.At the time, the main utility of (chloromethyl)dimethylphenylsilane was as the starting material for conversion to the corresponding Grignard reagent (see below). Since then, it has also been used for heteroatom alkylation, carbon alkylation, and conversion to a variety of organometallic and organolanthanide reagents. The main advantage of this reagent over the closely related (chloromethyl)trimethylsilane is the ability of (chloromethyl)dimethylphenylsilane to undergo a Fleming oxidation, thus allowing (chloromethyl)dimethylphenylsilane to serve as a masked hydroxyl group. This utility has been exploited for both the C-substituted and Nsubstituted adducts. A major disadvantage of the use of (chloromethyl)dimethylphenylsilane is its propensity to undergo rearrangements under a variety of conditions (see below). (Chloromethyl) dimethylphenylsilane is used as the precursor for the preparation of (phenyldimethylsilyl)methoxymethyl chloride (SMOM-Cl), a hydroxyl protecting group.
(Chloromethyl)dimethylphenylsilane (1) can be utilized to install a silylmethyl group on carbon via base promoted C-alkylation of terminal alkynes,dihydropyrazines,malonic esters,phenylacetonitriles,sulfoxides,and imines.Although has been used directly in the alkylation, conversion to the corresponding iodide via Finkelstein displacement (eq 1) prior to alkylation is sometimeswarranted. Except for the malonic esters (eq 2), strongly basic conditions and lowtemperatures (with slow warming) are generally employed in the transformation (eqs 3 and 4).	CHLOROMETHYLDIMETHYLPHENYLSILANE
Preparationcan be prepared either by the reaction of phenylmagnesium bromide with chloro(chloromethyl)dimethylsilane in ether at reflux,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.
CHLOROMETHYLDIMETHYLPHENYLSILANE Preparation Products And Raw materials
2-ETHYLBUTYLZINC BROMIDE 3-CHLOROPHENYLMAGNESIUM BROMIDE Magnesium, bromocyclobutyl- 1-ETHYLPENTYLZINC BROMIDE DIMETHYLPHENYLSILYLMETHYLMAGNESIUM CHLORIDE, 0.50 M in 2-MeTHF 1-ETHYLBUTYLZINC BROMIDE 2-BUTYLZINC BROMIDE PHENYLETHYNYLMAGNESIUM BROMIDE TRI-N-OCTYLALUMINIUM PHENYLTRIMETHYLSILANE CHLOROMETHYLPHENYLSILANE CHLOROMETHYLDIMETHYLSILANE CHLOROMETHYL(4-CHLOROPHENYL)DIMETHYLSILANE (CHLOROMETHYL)METHYLBIS(PENTAFLUOROPHENYL)SILANE DIMETHYLSILANE Chloromethyltrimethylsilane CHLOROMETHYLDIMETHYLPHENYLSILANE Chloromethyl silane

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