Summary
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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| Preferred IUPAC name
Phenylsilane | |||
| Other names
Silylbenzene
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3D model (JSmol)
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| ECHA InfoCard | 100.010.703 | ||
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CompTox Dashboard (EPA)
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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) | ||
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| Danger | |||
| H225, H261, H302, H315, H319, H332, H335 | |||
| P210, P301+P312+P330, P302+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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Infobox references
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Synthesis and reactions
editPhenylsilane 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
editPhenylsilane 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]
References
edit- ^ "Phenylsilane".
- ^ Minge, O.; Mitzel, N. W.; and Schmidbaur, H. Synthetic Pathways to Hydrogen-Rich Polysilylated Arenes from Trialkoxysilanes and Other Precursors. Organometallics 2002, 21, 680-684. doi:10.1021/om0108595
- ^ Weber, W. P. Silicon Reagents for Organic Synthesis. Springer-Verlag: Berlin, 1983. ISBN 0-387-11675-3.
- ^ Fleck, T. J. (2001). "Phenylsilane–Cesium Fluoride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rp101. ISBN 0471936235.
- ^ Hoffnagle, Alexander M.; Tezcan, F. Akif (2023-06-23). "Atomically Accurate Design of Metalloproteins with Predefined Coordination Geometries". Journal of the American Chemical Society. 145 (26): 14208–14214. doi:10.1021/jacs.3c04047. ISSN 0002-7863. PMC 10439731. PMID 37352018.