17878-13-6

Basic information

• Product Name: dimethyl(phenyl)silanecarboxylic acid
• Synonyms: dimethyl(phenyl)silanecarboxylic acid
• CAS NO: 17878-13-6
• Molecular Weight: 180.279
• Mol File: 17878-13-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: dimethyl(phenyl)silanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl(phenyl)silanecarboxylic acid(17878-13-6)
• EPA Substance Registry System: dimethyl(phenyl)silanecarboxylic acid(17878-13-6)

Safety Data

• Hazardous Substances Data: 17878-13-6(Hazardous Substances Data)

Upstream product

• 124-38-9 carbon dioxide 
• 768-33-2 phenyldimethylsilyl chloride 

Downstream Products

• 1349697-24-0 PhMe₂Si-O₂C-SiMe₂Ph 
• 611-94-9 4-Methoxybenzophenone 
• 1373360-31-6 benzyl 3-(dimethyl(phenyl)silyl)propanoate 
• 5272-18-4 dimethylphenylsilanol 
• 100229-29-6 tetrakis(μ-phenyldimethylsilanecarboxylato)bis[aquocopper(II)] 

Relevant articles and documents

Sila- and Germacarboxylic Acids: Precursors for the Corresponding Silyl and Germyl Radicals

Silicon-containing compounds are widely used as synthetic building blocks, functional materials, and bioactive reagents. In particular, silyl radicals are important intermediates for the synthesis and transformation of organosilicon compounds. Herein, we describe the first protocol for the generation of silyl radicals by photoinduced decarboxylation of silacarboxylic acids, which can be easily prepared in high yield on a gram scale and are very stable to air and moisture. Irradiation of silacarboxylic acids with blue LEDs (455 nm) in the presence of a commercially available photocatalyst releases silyl radicals, which can further react with various alkenes to give the corresponding silylated products in good-to-high yields with broad functional-group compatibility. This reaction proceeds in the presence of water, enabling efficient deuterosilylation of alkenes with D2O as the deuterium source. Germyl radicals were similarly obtained.

Silacarboxylic acids as efficient carbon monoxide releasing molecules: Synthesis and application in palladium-catalyzed carbonylation reactions

Silacarboxylic acids have been demonstrated to be easy to handle, air-stable carbon monoxide precursors. Different silacarboxylic acids were synthesized from the corresponding chlorosilanes and carbon dioxide, and their decarbonylation, upon treatment with an array of activators, was evaluated. The release of CO from crystalline MePh2SiCO2H proved to be highly efficient, and it was successfully applied in a selection of palladium-catalyzed carbonylative couplings using near-stoichiometric quantities of carbon monoxide precursor. Finally, the synthesis of MePh2Si 13CO2H and its application in carbonyl labeling of two bioactive compounds was demonstrated.