853955-69-8

Usage

Appearance

Colorless liquid

Molecular weight

234.38 g/mol

Melting point

-52°C

Derivative

Benzyl alcohol with a dimethylphenylsilyl group attached to the benzene ring

Usage

Reagent in organic synthesis (formation of carbon-carbon and carbon-silicon bonds), pharmaceutical and chemical industries (synthesis of various organic compounds)

Upstream product

• 321903-29-1 1,1-dimethyl-1,3-dihydrobenzo[c][1,2]oxasilole 
• 100-58-3 phenylmagnesium bromide 
• 108-86-1 bromobenzene 
• 768-33-2 phenyldimethylsilyl chloride 
• 1352196-85-0 C₁₅H₁₇BrOSi 
• 18982-54-2 o-bromobenzyl alcohol 
• 17100-66-2 2-(tetrahydropyranyloxy)methylbromobenzene 
• 853955-58-5 dimethyl(2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)phenyl)silane 

Downstream Products

• 2920-38-9 4-cyano-1,1'-biphenyl 
• 64145-51-3 3-phenylcyclopentanone 
• 64145-51-3 (R)-3-phenylcyclopentanone 
• 74395-08-7 3-phenylcycloheptanone 
• 61198-49-0 4-phenyltetrahydropyran-2-one 
• 772-13-4 3-phenylbutanonamide 
• 86-34-0 phensuximide 
• 2286-54-6 3,3-diphenyl-propionitrile 
• 162239-77-2 (R)-5-methyl-4-phenyl-hexan-2-one 
• 501919-45-5 (4S)-4-phenylnonan-2-one 
• 2550-26-7 4-Phenyl-2-butanone 
• 20795-53-3 (R)-3-phenylcyclohexanone 
• 1666-96-2 3-phenylquinoline 
• 321903-29-1 1,1-dimethyl-1,3-dihydrobenzo[c][1,2]oxasilole 

Relevant academic research and scientific papers

Copper-catalyzed electrophilic amination of arylsilanes with hydroxylamines

A copper-catalyzed electrophilic amination of aryl[(2-hydroxymethyl)phenyl] dimethylsilanes with O-acylated hydroxylamines has been developed to afford the corresponding anilines in good yields. The catalytic reaction proceeds very smoothly under mild conditions and tolerates a wide range of functional groups.

Improved Hiyama cross-coupling reactions using HOMSi

Various parameters in the Hiyama cross-coupling reaction of HOMSi reagents with ethyl bromobenzoate were studied. These included solvent, ligand, palladium source, and added water. DMF and THF were found to be excellent solvents. Palladium chloride was found to be the best palladium source and no added water was required. The use of tri-o-tolylphosphine as the ligand proved to be particularly effective.

Intramolecular nucleophilic attack at silicon in o-silylbenzyl alcohols. Generation of allyl and benzyl anion equivalents

Substituted silyl ethers of o-bromobenzyl alcohols and the derived o-silylbenzyl alcohols were used to transfer allyl and benzyl groups from silicon to the electrophiles benzaldehyde and benzophenone in excellent yields. γ-Oxidosilane intermediates (and possibly hypercoordinated silicon intermediates) are postulated.

Silicon-Based Cross-Coupling Reagent and Production Method of Organic Compound Using the Same

In one embodiment of the present invention, a silicon-based cross-coupling reagent is disclosed which is a highly stable tetraorganosilicon compound allowing for a cross-coupling reaction under mild reaction conditions without using fluoride ions, transition metal promoter, or strong bases, and the residue of the silicon reagent can be recovered and reused. The silicon-based cross-coupling reagent is a silicon compound in which an o-hydroxymethylphenyl group is connected to a silicon atom for intramolecular activation.

Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: An entry to tetraorganosilicon reagents for the silicon-based cross-coupling reaction

Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes, highly stable tetraorganosilicon reagents, are found to react with aryl and alkenyl iodides in the presence of a palladium catalyst and K2CO3 as a base, significantly milder conditions compared with those ever reported for the silicon-based cross-coupling reactions. The reaction tolerates a wide range of functional groups, including silyl protectors, and allows a gram-scale synthesis to recover and reuse the silicon residue. Copyright