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HomeProduct name listCHLOROMETHYLDIMETHYLPHENYLSILANE

CHLOROMETHYLDIMETHYLPHENYLSILANE

  • CAS NO.:1833-51-8
  • Empirical Formula: C9H13ClSi
  • Molecular Weight: 184.74
  • MDL number: MFCD00040858
  • EINECS: 217-392-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-06-08 17:06:38
CHLOROMETHYLDIMETHYLPHENYLSILANE Structural

What is CHLOROMETHYLDIMETHYLPHENYLSILANE?

Physical properties

bp 106–107°C/15 mmHg; d 1.024 g cm?3

The Uses of CHLOROMETHYLDIMETHYLPHENYLSILANE

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).	CHLOROMETHYLDIMETHYLPHENYLSILANE

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.

Properties of CHLOROMETHYLDIMETHYLPHENYLSILANE

Boiling point: 106-107 °C/15 mmHg (lit.)
Density  1.024 g/mL at 25 °C (lit.)
refractive index  n20/D 1.520(lit.)
Flash point: 196 °F
storage temp.  2-8°C
form  clear liquid
Specific Gravity 1.031
color  Colorless to Almost colorless
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 information for CHLOROMETHYLDIMETHYLPHENYLSILANE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for CHLOROMETHYLDIMETHYLPHENYLSILANE

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