Benzyldimethylsilane

Base Information

• Chemical Name: Benzyldimethylsilane
• CAS No.: 1631-70-5
• Molecular Formula: C9H14 Si
• Molecular Weight: 150.296
• Hs Code.: 2931900090
• European Community (EC) Number: 624-907-1
• NSC Number: 155373
• DSSTox Substance ID: DTXSID30883702
• Mol file: 1631-70-5.mol

Synonyms:Benzyldimethylsilane;1631-70-5;benzyl(dimethyl)silicon;Benzene, [(dimethylsilyl)methyl]-;Dimethyl(phenylmethyl)silane;Silane, dimethyl(phenylmethyl)-;Benzene, ((dimethylsilyl)methyl)-;NSC 155373;dimethylbenzylsilane;?Benzyldimethylsilane;NSC155373;Benzyldimethylsilane, 99%;C([Si](C)C)c1ccccc1;DTXSID30883702;DIMETHYLBENZYLSILANE (1-D);BAA63170;MFCD00039792;AKOS008901201;NSC-155373;AS-77782;CS-0129591;FT-0622842;D89172;S00975;A903961

Chemical Property of Benzyldimethylsilane

Chemical Property:

• Melting Point: <0°C
• Refractive Index: n20/D 1.502(lit.)
• Boiling Point: 69-71 ºC (15 mmHg)
• Flash Point: 56 ºC
• PSA: 0.00000
• Density: 0.949
• LogP: 2.52140
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 149.078651949
• Heavy Atom Count: 10
• Complexity: 82.7

Purity/Quality:

97% ^*data from raw suppliers

Benzyldimethylsilane ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)CC1=CC=CC=C1
• General Description: Benzyldimethylsilane is a silicon-based reagent used in palladium-catalyzed Hiyama coupling reactions, particularly for cross-coupling with electron-deficient vinylsilanes like α-silylenoates and α-silylenamides. It serves as a hydrosilylation agent under optimized conditions, contributing to the formation of alkene products with good yields and high stereoselectivity when paired with a silver additive and appropriate reaction parameters. Its utility in synthetic chemistry lies in its role as a key component in facilitating selective C-C bond formation.

Technology Process of Benzyldimethylsilane

There total 7 articles about Benzyldimethylsilane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

dimethylmonochlorosilane (1066-35-9) + benzyl bromide (100-39-0) → benzyldimethylsilane (1631-70-5)

Guidance literature:

With iodine; magnesium; In tetrahydrofuran; at 0 - 20 ℃; for 17h; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.7b04364

Reference yield: 78.0%

benzyl(chloro)dimethylsilane (1833-31-4) → benzyldimethylsilane (1631-70-5)

Guidance literature:

With sodium tetrahydroborate; In acetonitrile; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jacs.0c03011

Reference yield: 16.5%

trichlorosilane (10025-78-2) + methylmagnesium chloride (676-58-4) + benzylmagnesium chloride (6921-34-2) → benzyldimethylsilane (1631-70-5)

Guidance literature:

In not given;

DOI:10.1021/jo01149a017

upstream raw materials:

benzylmagnesium chloride

benzyl(chloro)dimethylsilane

benzyl chloride

dimethylsilicon dichloride

Downstream raw materials:

benzyldimethyl(2-phenylethyl)silane

(Benzyl-dimethyl-silanyl)-acetic acid ethyl ester

benzyl(hexyl)dimethylsilane

γ-Acetoxypropyl-benzyl-dimethylsilan

Refernces

Palladium-catalyzed hiyama couplings of α-silylenoates and α-silylenamides

10.1021/ol301300r

The research focuses on the Hiyama couplings of R-silylenoates and R-silylenamides, which are sensitive substrate classes that require specific conditions for high yield coupling products. The purpose of this study was to develop a method for the cross-coupling of these electron-deficient vinylsilanes, utilizing palladium-catalyzed reactions with appropriate silicon-based species and a silver additive. The researchers found that the choice of silane species and reaction conditions were crucial for a successful hydrosilylation/C-C bond-formation process. They used a variety of chemicals in their process, including 2-pyridyldimethylsilane, allyl- and benzyldimethylsilane, and 1,1,1,3,5,5,5-heptamethyltrisiloxane, among others. The conclusions of the research indicated that under carefully controlled conditions and with the appropriate silicon species, alkene products could be obtained in good yields and with high geometrical integrity, making this transformation valuable for synthetic chemists.