1309154-13-9

Basic information

• Product Name: (2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)dimethyl(phenyl)silane
• CAS NO: 1309154-13-9
• Molecular Weight: 324.303
• Mol File: 1309154-13-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)dimethyl(phenyl)silane(CAS DataBase Reference)
• NIST Chemistry Reference: (2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)dimethyl(phenyl)silane(1309154-13-9)
• EPA Substance Registry System: (2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)dimethyl(phenyl)silane(1309154-13-9)

Safety Data

• Hazardous Substances Data: 1309154-13-9(Hazardous Substances Data)

Upstream product

• 100-58-3 phenylmagnesium bromide 
• 130350-97-9 (o-bromophenyl)dimethylsilyl chloride 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 81759-74-2 2-isopropoxy-5,5-dimethyl-1,3,2-dioxaborinane 
• 1160757-56-1 C₁₄H₁₅BrSi 

Downstream Products

• 1160757-32-3 1,1-dimethyl-2,3-dipropyl-1H-benzo[b]silole 
• 1160757-47-0 1-methyl-1-phenyl-2,3-dipropyl-1H-benzo[b]silole 
• 1016642-73-1 1,1-dimethyl-2,3-diphenyl-1H-benzo[b]silole 
• 1309154-21-9 1-methyl-1,2,3-triphenyl-1H-benzo[b]silole 

Relevant articles and documents

Rhodium-catalyzed carbon-silicon bond activation for synthesis of benzosilole derivatives

A rhodium-catalyzed coupling reaction of 2-trimethylsilylphenylboronic acid with internal alkynes is developed for the synthesis of 2,3-disubstituted benzosilole derivatives. A range of functional groups, encompassing ketones, esters, amines, aryl bromides, and heteroarenes, are compatible, which provides rapid access to diverse benzosiloles. Sequential 2-fold coupling enables modular synthesis of asymmetrically substituted 1,5-dihydro-1,5-disila-s-indacene, a π-extended molecule of interest in organic electronics. In terms of the mechanism, the reaction involves cleavage of a C(alkyl)-Si bond in a trialkylsilyl group, which normally requires extremely harsh conditions for activation. Mechanistic studies, including effects of substituents, reveal that C-Si bond cleavage does not proceed through a hypercoordinated silicon species, but rather through a rhodium-mediated activation process. The potential use of the reaction in catalytic asymmetric synthesis of Si-chiral benzosiloles is also demonstrated.