1833-51-8 Usage
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.
Check Digit Verification of cas no
The CAS Registry Mumber 1833-51-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,3 and 3 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1833-51:
(6*1)+(5*8)+(4*3)+(3*3)+(2*5)+(1*1)=78
78 % 10 = 8
So 1833-51-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H13ClSi/c1-11(2,8-10)9-6-4-3-5-7-9/h3-7H,8H2,1-2H3
1833-51-8Relevant articles and documents
Martel,Aly
, p. 61,67,70 (1971)
The β-silicon effect. 4: Substituent effects on the solvolysis of 1-alkyl-2-(aryldimethylsilyl)ethyl trifluoroacetates
Fujiyama, Ryoji,Alam, Md. Ashadul,Shiiyama, Aiko,Munechika, Toshihiro,Fujio, Mizue,Tsuno, Yuho
experimental part, p. 819 - 827 (2011/04/24)
Solvolysis rates of 2-(aryldimethylsilyl)-1-methylethyl and 2-(aryldimethylsilyl)-1-tert-butylethyl trifluoroacetates were determined conductimetrically in 60% (v/v) aqueous ethanol. The effects of aryl substituents at the silicon atom on the solvolysis rates at 50 °C were correlated with σmacr; parameters of r+ = 0.15 with the Yukawa-Tsuno equation, giving ρ values of-1.5 for both secondary α-Me and α-tert-Bu systems. The ρ values for those secondary systems are less negative than-1.75 for the 2-(aryldimethylsilyl)ethyl system that proceeds by the Eaborn (non-vertical) mechanism, while they are distinctly more negative than-0.99 for 2-(aryldimethylsilyl)-1-phenylethyl system that should proceed by the Lambert (vertical) mechanism. There was a fairly linear relationship between the reaction constants (ρ) for the β-silyl substituent effects and the solvolysis reactivities for a series of β-silyl substrates. The solvolyses of the α-Me and tert-Bu substrates proceed through the transition state (TS) with an appreciable degree of the β-silyl participation, close to the Eaborn (non-vertical) TS rather than to the Lambert (vertical) TS. Copyright
Silver-catalyzed transmetalation between chlorosilanes and aryl and alkenyl Grignard reagents for the synthesis of tetraorganosilanes
Murakami, Kei,Hirano, Koji,Yorimitsu, Hideki,Oshima, Koichiro
supporting information; experimental part, p. 5833 - 5835 (2009/03/11)
(Chemical Equation Presented) The silver savior: Nucleophilic substitution reactions of chlorosilanes with aryl Grignard reagents have been developed which take place under silver catalysis to afford tetraorganosilanes (see scheme). This transformation is likely to be promoted by diarylargentate reagents that are generated in situ.