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ChemicalBook--->CAS DataBase List--->1833-51-8

1833-51-8

1833-51-8 Structure

1833-51-8 Structure
IdentificationMore
[Name]

CHLOROMETHYLDIMETHYLPHENYLSILANE
[CAS]

1833-51-8
[Synonyms]

CHLOROMETHYLDIMETHYLPHENYLSILANE
(chloromethyl)dimethylphenyl-silan
Dichloromethyldimethylphenylsilane
Phenyldimethyl(chloromethyl)silane
Silane, (chloromethyl)dimethylphenyl-
Chloromethylphenyldimethylsilane
Phenyl(chloromethyl)dimethylsilane
Dimethylphenylsilyldichloromethane
[EINECS(EC#)]

217-392-6
[Molecular Formula]

C9H13ClSi
[MDL Number]

MFCD00040858
[Molecular Weight]

184.74
[MOL File]

1833-51-8.mol
Chemical PropertiesBack Directory
[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 Gravity]

1.031
[Hydrolytic Sensitivity]

4: no reaction with water under neutral conditions
[BRN ]

2935991
[CAS DataBase Reference]

1833-51-8(CAS DataBase Reference)
[EPA Substance Registry System]

Silane, (chloromethyl)dimethylphenyl- (1833-51-8)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[RIDADR ]

1993
[WGK Germany ]

3
[TSCA ]

Yes
[HS Code ]

29319000
Hazard InformationBack Directory
[Physical properties]

bp 106–107°C/15 mmHg; d 1.024 g cm?3
[Uses]

The 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).

[Preparation]

can 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.
Spectrum DetailBack Directory
[Spectrum Detail]

CHLOROMETHYLDIMETHYLPHENYLSILANE(1833-51-8)MS
CHLOROMETHYLDIMETHYLPHENYLSILANE(1833-51-8)1HNMR
CHLOROMETHYLDIMETHYLPHENYLSILANE(1833-51-8)13CNMR
CHLOROMETHYLDIMETHYLPHENYLSILANE(1833-51-8)IR1
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

1833-51-8(sigmaaldrich)
[TCI AMERICA]

Chloromethyldimethylphenylsilane,>95.0%(GC)(1833-51-8)
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