Phenylsilane
Chemical compound
From Wikipedia, the free encyclopedia
Phenylsilane, also known as silylbenzene, a colorless liquid, is one of the simplest organosilanes with the formula C6H5SiH3. It is structurally related to toluene, with a silyl group replacing the methyl group. Both of these compounds have similar densities and boiling points due to these similarities. Phenylsilane is soluble in organic solvents.
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| Names | |||
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| Preferred IUPAC name
Phenylsilane | |||
| Other names
Silylbenzene | |||
| Identifiers | |||
3D model (JSmol) |
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| ECHA InfoCard | 100.010.703 | ||
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| Properties | |||
| C6H8Si | |||
| Molar mass | 108.215 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Density | 0.878 g/cm3 | ||
| Boiling point | 119 to 121 °C (246 to 250 °F; 392 to 394 K) | ||
| Hydrolyzes | |||
| Hazards[1] | |||
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| Danger | |||
| H225, H302+H332, H315, H319, H335 | |||
| P210, P233, P301+P312, P303+P361+P353, P304+P340+P312, P305+P351+P338 | |||
| Safety data sheet (SDS) | MSDS | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and reactions
Phenylsilane is produced in two steps from Si(OEt)4. In the first step, phenylmagnesium bromide is added to form Ph−Si(OEt)3 via a Grignard reaction. Reduction of the resulting Ph−Si(OEt)3 product with LiAlH4 affords phenylsilane.[2]
- Ph−MgBr + Si(OEt)4 → Ph−Si(OEt)3 + MgBr(OEt)
- 4 Ph−Si(OEt)3 + 3 LiAlH4 → 4 Ph−SiH3 + 3 LiAl(OEt)4
Uses
Phenylsilane can be used to reduce tertiary phosphine oxides to the corresponding tertiary phosphine.
- P(CH3)3O + PhSiH3 → P(CH3)3 + PhSiH2OH
The use of phenylsilane proceeds with retention of configuration at the phosphine. For example, cyclic chiral tertiary phosphine oxides can be reduced to cyclic tertiary phosphines.[3]
Phenylsilane combines with caesium fluoride to give the ate complex [PhSiFH3]−. This species functions as a hydride donor, reducing 4-oxazolium salts to 4-oxazolines.[4]
Phenylsilane has been used as a hydride donor in synthetic enzymes.[5]