1833-51-8 Usage
Description
Chloromethyldimethylphenylsilane is an organosilicon compound with the molecular formula (chloromethyl)dimethylphenylsilane. It was first reported in 1949 and has since been used in various chemical reactions and applications due to its unique properties.
Uses
1. Used in Chemical Synthesis:
Chloromethyldimethylphenylsilane is used as a starting material for the conversion to the corresponding Grignard reagent. This application is beneficial for heteroatom alkylation, carbon alkylation, and the creation of various organometallic and organolanthanide reagents.
2. Used as a Masked Hydroxyl Group:
Chloromethyldimethylphenylsilane is used as a masked hydroxyl group, thanks to its ability to undergo a Fleming oxidation. This utility has been exploited for both C-substituted and N-substituted adducts.
3. Used in the Preparation of (Phenylmethylsilyl)methoxymethyl Chloride (SMOM-Cl):
Chloromethyldimethylphenylsilane is used as a precursor for the preparation of SMOM-Cl, a hydroxyl protecting group.
4. Used in C-Alkylation:
Chloromethyldimethylphenylsilane can be utilized to install a silylmethyl group on carbon via base-promoted C-alkylation of various compounds, such as terminal alkynes, dihydropyrazines, malonic esters, phenylacetonitriles, sulfoxides, and imines.
5. Used in Alkylation with Corresponding Iodide:
In some cases, Chloromethyldimethylphenylsilane is first converted to the corresponding iodide via Finkelstein displacement before undergoing alkylation. This method is sometimes warranted for better results.
Physical Properties:
Boiling Point: 106-107°C at 15 mmHg
Density: 1.024 g/cm3
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.
