dimethylphenylsilane

Dimethylphenylsilane, also known as phenyl(dimethyl)silane, is an organosilicon compound with the formula C8H12Si. The silicon center is bonded to a phenyl group, two methyl groups, and a hydride, giving the configuration PhSiHMe2. It is categorized as a hydrosilane and is used as a reagent in various silicon- and carbon-bond-forming reactions.

Synthesis and availability

Dimethylphenylsilane can be prepared by several routes described in the literature, including reduction of suitable chlorosilane precursors and metal-catalyzed C–H silylation or hydrosilylation processes that form the Si–C bond to the aryl group. It is also sold by chemical suppliers as a laboratory reagent. The exact preparation method chosen depends on the desired scale and accompanying functional groups.

Reactivity and applications

As a hydrosilane, dimethylphenylsilane participates in hydrosilylation reactions where the Si–H bond transfers across multiple substrates, typically under transition-metal catalysis, to form Si–C bonds. The compound provides a source of the dimethylsilyl group for further functionalization and serves as a building block for arylsilane derivatives. The Si–H bond is reactive toward oxidation and hydrolysis; exposure to moisture or air can lead to silanol formation and, under hydrolytic conditions, release of hydrogen gas.

Safety and handling

Dimethylphenylsilane is an organosilicon reagent and should be handled with standard laboratory precautions. It is generally stored under inert atmosphere to prevent hydrolysis or oxidation. It can be flammable and irritant, so appropriate ventilation, eye protection, and avoidance of inhalation are advised.

See also

Organosilicon compounds; hydrosilanes; arylsilane chemistry.