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{{chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 402835827 |
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| Watchedfields = changed |
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| Name = Phenylsilane |
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| verifiedrevid = 413074484 |
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| ImageFileL1 = Phenylsilane.png |
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| Name = Phenylsilane |
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| ImageSizeL1 = 80 px |
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| ImageFileL1 = Phenylsilane.png |
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| ImageNameL1 = skeletal formula of phenylsilane |
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| ImageSizeL1 = 80 px |
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| ImageFileR1 = Phenylsilane-3D-vdW.png |
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| ImageNameL1 = skeletal formula of phenylsilane |
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| ImageSizeR1 = 120 px |
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| ImageFileR1 = Phenylsilane-3D-vdW.png |
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| ImageNameR1 = ball-and-stick model of the phenylsilane molecule |
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| ImageNameR1 = ball-and-stick model of the phenylsilane molecule |
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| OtherNames = Silylbenzene |
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| PIN = Phenylsilane |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = Silylbenzene |
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| CASNo = 694-53-1 |
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|Section1={{Chembox Identifiers |
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}} |
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| CASNo = 694-53-1 |
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| Section2 = {{Chembox Properties |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Formula = C<sub>6</sub>H<sub>8</sub>Si |
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| EINECS = 211-772-5 |
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| MolarMass = 108.22 g/mol |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| Appearance = Colorless liquid |
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| UNII = P2EX7Q1UYS |
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| Density = 0.878 g/cm³ |
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| PubChem = 12752 |
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| Solubility in water = N/A (very reactive with water) |
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| MeltingPt = N/A |
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| ChEBI = 172874 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| BoilingPt = 119-121 °C (433-394 K) |
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| ChemSpiderID = 12228 |
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}} |
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| SMILES = c1ccccc1 |
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| Section3 = {{Chembox Hazards |
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| InChI = 1/C6H8Si/c7-6-4-2-1-3-5-6/h1-5H,7H3 |
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| MSDS = |
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| InChIKey = PARWUHTVGZSQPD-UHFFFAOYAT |
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| RPhrases = 11-14/15-20/22-36/37/38 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| SPhrases = 16-43 |
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| StdInChI = 1S/C6H8Si/c7-6-4-2-1-3-5-6/h1-5H,7H3 |
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}} |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = PARWUHTVGZSQPD-UHFFFAOYSA-N |
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}} |
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|Section2={{Chembox Properties |
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| C=6 | H=8 | Si=1 |
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| Appearance = Colorless liquid |
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| Density = 0.878 g/cm<sup>3</sup> |
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| Solubility = Hydrolyzes |
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| MeltingPt = |
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| BoilingPtC = 119 to 121 |
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|Section4={{Chembox Hazards |
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| ExternalSDS = |
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| Hazards_ref = <ref>{{cite web |title=Phenylsilane |url=https://www.sigmaaldrich.com/AU/en/product/ALDRICH/335150}}</ref> |
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| GHSPictograms = {{GHS02}}{{GHS07}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|225|261|302|315|319|332|335}} |
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| PPhrases = {{P-phrases|210|301+312+330|302+353|304+340+312|305+351+338}} |
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'''Phenylsilane''', also known as '''silylbenzene''', a colorless liquid, is one of the simplest ]s with the formula ]<sub>6</sub>]<sub>5</sub>]H<sub>3</sub>. It is structurally related to ], with a silyl group replacing the ] 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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'''Phenylsilane''', also known as '''silylbenzene''', a colorless liquid, is one of the simplest ]s with the formula ]<sub>6</sub>]<sub>5</sub>]H<sub>3</sub>. It is structurally related to ], with a silyl group replacing the ] 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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==Synthesis and reactions== |
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==Synthesis and reactions== |
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Phenylsilane is produced in two steps from Si(OEt)<sub>4</sub>. In the first step, phenylmagnesium bromide is added to form Ph-Si(OEt)<sub>3</sub> via a ]. Reduction of the resulting Ph-Si(OEt)<sub>3</sub> product with LiAlH<sub>4</sub> affords phenylsilane<ref>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}}</ref>. |
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Phenylsilane is produced in two steps from Si(OEt)<sub>4</sub>. In the first step, ] is added to form Ph−Si(OEt)<sub>3</sub> via a ]. Reduction of the resulting Ph−Si(OEt)<sub>3</sub> product with LiAlH<sub>4</sub> affords phenylsilane.<ref>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}}</ref> |
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Ph-MgBr + Si(OEt)<sub>4</sub> → Ph-Si(OEt)<sub>3</sub> + MgBr(OEt) |
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:Ph−MgBr + Si(OEt)<sub>4</sub> → Ph−Si(OEt)<sub>3</sub> + MgBr(OEt) |
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4 Ph-Si(OEt)<sub>3</sub> + 3 LiAlH<sub>4</sub> → 4 Ph-SiH<sub>3</sub> + 3 LiAl(OEt)<sub>4</sub> |
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:4 Ph−Si(OEt)<sub>3</sub> + 3 LiAlH<sub>4</sub> → 4 Ph−SiH<sub>3</sub> + 3 LiAl(OEt)<sub>4</sub> |
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==Uses== |
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==Uses== |
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Phenylsilane can be used to reduce tertiary ]s to the corresponding tertiary ]. |
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Phenylsilane can be used to reduce tertiary ]s to the corresponding tertiary ]. |
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P(CH<sub>3</sub>)<sub>3</sub>O + PhSiH<sub>3</sub> --> P(CH<sub>3</sub>)<sub>3</sub> + PhSiH<sub>2</sub>OH |
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:P(CH<sub>3</sub>)<sub>3</sub>O + PhSiH<sub>3</sub> → P(CH<sub>3</sub>)<sub>3</sub> + PhSiH<sub>2</sub>OH |
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The use of phenylsilane proceeds with ] at the phosphine. For example, cyclic chiral tertiary phosphine oxides can be reduced to cyclic tertiary phosphines<ref>Weber, W. P. ''Silicon Reagents for Organic Synthesis''. Springer-Verlag: Berlin, 1983. ISBN 0387116753.</ref>. |
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The use of phenylsilane proceeds with ] at the phosphine. For example, cyclic chiral tertiary phosphine oxides can be reduced to cyclic tertiary phosphines.<ref>Weber, W. P. ''Silicon Reagents for Organic Synthesis''. Springer-Verlag: Berlin, 1983. {{ISBN|0-387-11675-3}}.</ref> |
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Phenylsilane can also be combined with ]. In ]s, it becomes a nonnucleophilic hydride donor. Specifically, phenylsilane-caesium fluoride has been shown to reduce 4-oxazolium salts to 4-oxazolines. This reduction gives yields of 95%<ref>Fleck, T. J. ''Encyclopedia of Reagents for Organic Synthesis'' {{doi|10.1002/047084289X.rp101}}</ref>. |
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Phenylsilane combines with ] to give the ] <sup>−</sup>. This species functions as a hydride donor, reducing 4-oxazolium salts to 4-]s.<ref>{{cite journal|author=Fleck, T. J.|journal=Encyclopedia of Reagents for Organic Synthesis|doi=10.1002/047084289X.rp101|title=Phenylsilane–Cesium Fluoride|year=2001|isbn=0471936235}}</ref> |
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Phenylsilane has been used as a ] donor in ].<ref>{{Cite journal |last1=Hoffnagle |first1=Alexander M. |last2=Tezcan |first2=F. Akif |date=2023-06-23 |title=Atomically Accurate Design of Metalloproteins with Predefined Coordination Geometries |journal=Journal of the American Chemical Society |volume=145 |issue=26 |pages=14208–14214 |language=en |doi=10.1021/jacs.3c04047 |pmid=37352018 |issn=0002-7863|pmc=10439731 }}</ref> |
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==References== |
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==References== |
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