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1833-51-8

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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

1833-51-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Detail
  • TCI America

  • (C1419)  Chloromethyldimethylphenylsilane  >97.0%(GC)

  • 1833-51-8

  • 5g

  • 550.00CNY

  • Detail
  • TCI America

  • (C1419)  Chloromethyldimethylphenylsilane  >97.0%(GC)

  • 1833-51-8

  • 25g

  • 1,650.00CNY

  • Detail
  • Aldrich

  • (347094)  (Chloromethyl)dimethylphenylsilane  98%

  • 1833-51-8

  • 347094-10G

  • 1,138.41CNY

  • Detail
  • Aldrich

  • (347094)  (Chloromethyl)dimethylphenylsilane  98%

  • 1833-51-8

  • 347094-50G

  • 3,937.05CNY

  • Detail

1833-51-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name chloromethyl-dimethyl-phenylsilane

1.2 Other means of identification

Product number -
Other names chloromethyl-phenyldimethylsilane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1833-51-8 SDS

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.

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