| Revision as of 05:31, 14 March 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - updated 'UNII_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoBot← Previous edit |
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{{chembox |
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{{Chembox |
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| Reference = <ref>, chemblink.com</ref><ref>, lookchem.com</ref> |
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| verifiedrevid = 396492848 |
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| verifiedrevid = 418735081 |
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| ImageFile = Hexamethyldisilane displayed.svg |
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| ImageFile2 = Hexamethyldisilane.svg |
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| ImageFile = Hexamethyldisilane.svg |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageSize = |
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| IUPACName = |
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| ImageSize = 160 |
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| ImageName = Skeletal formula of hexamethyldisilane |
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| OtherNames = |
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| ImageFileL1 = Hexamethyldisilane-3D-balls.png |
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| Section1 = {{Chembox Identifiers |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| Abbreviations = |
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| ImageAltL1 = Ball-and-stick model |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ImageFileR1 = Hexamethyldisilane-3D-spacefill.png |
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| ChemSpiderID = 66675 |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| InChIKey = NEXSMEBSBIABKL-UHFFFAOYAV |
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| ImageAltR1 = Space-filling model |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| PIN = Hexamethyldisilane |
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| StdInChI = 1S/C6H18Si2/c1-7(2,3)8(4,5)6/h1-6H3 |
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|Section1={{Chembox Identifiers |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = NEXSMEBSBIABKL-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 1450-14-2 |
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| CASNo = 1450-14-2 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = A7HH2E9DUB |
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| PubChem = 74057 |
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| ChemSpiderID = 66675 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| EINECS = 215-911-0 |
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| EINECS = 215-911-0 |
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| PubChem = |
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| UNNumber = 1993 |
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| RTECS = JM9170000 |
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| Beilstein = 1633463 |
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| SMILES = C(C)(C)(C)(C)C |
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| SMILES = C(C)(C)(C)(C)C |
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| InChI = 1/C6H18Si2/c1-7(2,3)8(4,5)6/h1-6H3 |
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| StdInChI = 1S/C6H18Si2/c1-7(2,3)8(4,5)6/h1-6H3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| RTECS = |
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| StdInChIKey = NEXSMEBSBIABKL-UHFFFAOYSA-N |
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| MeSHName = |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEBI = |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = |
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| ATCCode_prefix = |
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| ATC_Supplemental =}} |
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| Section2 = {{Chembox Properties |
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| C=6|H=18|Si=2 |
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| Appearance = |
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| Density = 0.715 g/mL |
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| MeltingPtC = 15 |
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| Melting_notes = |
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| BoilingPt = 112-114 °C |
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| Solvent = |
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| pKa = |
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| pKb = }} |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = |
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| NFPA-R = |
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| NFPA-O = |
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| RPhrases = {{R11}} |
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| SPhrases = {{S16}} {{S33}} {{S9}} |
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| RSPhrases = |
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| FlashPt = 11 °C |
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| Autoignition = |
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| ExploLimits = |
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| PEL = }} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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| Formula = Si<sub>2</sub>C<sub>6</sub>H<sub>18</sub> |
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| MolarMass = 146.39 g mol<sup>−1</sup> |
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| Appearance = Colourless liquid |
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| Density = 0.715 g/cm<sup>3</sup> |
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| MeltingPtK = 287 |
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| BoilingPtK = 386 |
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| RefractIndex = 1.422 |
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}} |
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|Section3={{Chembox Thermochemistry |
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| Entropy = 255.89 J K<sup>−1</sup> mol<sup>−1</sup> (at 22.52 °C) |
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}} |
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|Section4={{Chembox Hazards |
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| GHSPictograms = {{GHS flame}}{{GHS exclamation mark}}{{GHS health hazard}} |
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| GHSSignalWord = '''DANGER''' |
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| HPhrases = {{H-phrases|225|319|334|335}} |
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| PPhrases = {{P-phrases|210|261|305+351+338|342+311}} |
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| FlashPtC = 11 |
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}} |
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|Section5={{Chembox Related |
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| OtherFunction_label = alkylsilanes |
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| OtherFunction = ]<br /> |
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] |
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}} |
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}} |
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'''Hexamethyldisilane''' (]<sub>2</sub>) is the ] with the formula Si<sub>2</sub>(CH<sub>3</sub>)<sub>6</sub>, abbreviated Si<sub>2</sub>Me<sub>6</sub>. It is a colourless liquid, soluble in organic solvents.<ref>Tamejiro Hiyama, Manabu Kuroboshi, "Hexamethyldisilane" Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons. {{doi|10.1002/047084289X.rh015}}</ref> |
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==Synthesis and reactions== |
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Hexamethyldisilane can be produced by ] of trimethylsilyl chloride in the presence of a reducing agent such as ]: |
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:{{chem2|2 Me3SiCl + 2 K -> Me3Si\sSiMe3 + 2 KCl}} |
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With an excess of the reductant, the alkali metal silyl derivative is produced:<ref>{{cite journal |doi=10.1016/0022-328X(88)80634-X|title=Efficient formation and cleavage of disilanes by potassium-graphite. Silylation with silyl metal reagents |year=1988 |last1=Fürstner |first1=Alois |last2=Weidmann |first2=Hans |journal=Journal of Organometallic Chemistry |volume=354 |pages=15–21 }}</ref> |
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:{{chem2|Me3Si\sSiMe3 + 2 K -> 2 Me3SiK}} |
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The Si-Si bond in hexamethyldisilane is cleaved by strong nucleophiles and electrophiles. Alkyl lithium compounds react as follows: |
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'''Hexamethyldisilane''' is a ] of the ] (TMS) group, linked through a silicon-silicon bond. |
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:Si<sub>2</sub>Me<sub>6</sub> + RLi → RSiMe<sub>3</sub> + LiSiMe<sub>3</sub> |
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Hexamethyldisilane is cleaved by ] to give ].<ref>{{cite journal | doi = 10.1016/0040-4020(82)87002-6 | title = Iodotrimethylsilane—a versatile synthetic reagent | year = 1982 | author = Olah, G.; Narang, S.C. | journal = ]| volume = 38 | issue = 15 | pages = 2225}}</ref> |
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] gives ].<ref>{{cite journal|doi=10.1016/0040-4020(82)87002-6|title=Iodotrimethylsilane—a versatile synthetic reagent|year=1982|author1=Olah, G. |author2=Narang, S.C. |journal=]|volume=38|issue=15|pages=2225}}</ref> |
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:Me<sub>3</sub>Si−SiMe<sub>3</sub> + I<sub>2</sub> → 2 SiMe<sub>3</sub>I |
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==References== |
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==References== |
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{{Reflist}} |
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{{Reflist}} |
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