Chemistry:Phenylsilane
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| Preferred IUPAC name
Phenylsilane | |||
| Other names
Silylbenzene
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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] | |||
| Safety data sheet | MSDS | ||
| GHS pictograms |  
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| GHS Signal word | Danger | ||
| H225, H261, H302, H315, H319, H332, H335 | |||
| P210, P301+312+330Script error: No such module "Preview warning".Category:GHS errors, P302+353Script error: No such module "Preview warning".Category:GHS errors, P304+340+312Script error: No such module "Preview warning".Category:GHS errors, P305+351+338 | |||
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 | |||
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.
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]
References
- ↑ "Phenylsilane". https://www.sigmaaldrich.com/AU/en/product/ALDRICH/335150.
- ↑ 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" (in en). Journal of the American Chemical Society 145 (26): 14208–14214. doi:10.1021/jacs.3c04047. ISSN 0002-7863. PMID 37352018.
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