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
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).
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 | n |
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) |
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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