{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 418735081 | ImageFile = Hexamethyldisilane.svg | ImageFile_Ref = {{chemboximage|correct|??}} | ImageSize = 160 | ImageName = Skeletal formula of hexamethyldisilane | ImageFileL1 = Hexamethyldisilane-3D-balls.png | ImageFileL1_Ref = {{chemboximage|correct|??}} | ImageAltL1 = Ball-and-stick model | ImageFileR1 = Hexamethyldisilane-3D-spacefill.png | ImageFileR1_Ref = {{chemboximage|correct|??}} | ImageAltR1 = Space-filling model | PIN = Hexamethyldisilane |Section1={{Chembox Identifiers | CASNo = 1450-14-2 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = A7HH2E9DUB | PubChem = 74057 | ChemSpiderID = 66675 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | EINECS = 215-911-0 | UNNumber = 1993 | RTECS = JM9170000 | Beilstein = 1633463 | SMILES = C[Si](C)(C)[Si](C)(C)C | StdInChI = 1S/C6H18Si2/c1-7(2,3)8(4,5)6/h1-6H3 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = NEXSMEBSBIABKL-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} }} |Section2={{Chembox Properties | Formula = Si<sub>2</sub>C<sub>6</sub>H<sub>18</sub> | MolarMass = 146.39 g mol<sup>−1</sup> | Appearance = Colourless liquid | Density = 0.715 g/cm<sup>3</sup> | MeltingPtK = 287 | BoilingPtK = 386 | RefractIndex = 1.422 }} |Section3={{Chembox Thermochemistry | Entropy = 255.89 J K<sup>−1</sup> mol<sup>−1</sup> (at 22.52 °C) }} |Section4={{Chembox Hazards | GHSPictograms = {{GHS flame}}{{GHS exclamation mark}}{{GHS health hazard}} | GHSSignalWord = '''DANGER''' | HPhrases = {{H-phrases|225|319|334|335}} | PPhrases = {{P-phrases|210|261|305+351+338|342+311}} | FlashPtC = 11 }} |Section5={{Chembox Related | OtherFunction_label = alkylsilanes | OtherFunction = Tetramethylsilane<br /> Triethylsilane }} }}
'''Hexamethyldisilane''' (TMS<sub>2</sub>) is the organosilicon compound 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> ==Synthesis and reactions== Hexamethyldisilane can be produced by Wurtz-like coupling of trimethylsilyl chloride in the presence of a reducing agent such as potassium graphite: :{{chem2|2 Me3SiCl + 2 K -> Me3Si\sSiMe3 + 2 KCl}} 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> :{{chem2|Me3Si\sSiMe3 + 2 K -> 2 Me3SiK}}
The Si-Si bond in hexamethyldisilane is cleaved by strong nucleophiles and electrophiles. Alkyl lithium compounds react as follows: :Si<sub>2</sub>Me<sub>6</sub> + RLi → RSiMe<sub>3</sub> + LiSiMe<sub>3</sub>
Iodine gives trimethylsilyl iodide.<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=Tetrahedron|volume=38|issue=15|pages=2225}}</ref> :Me<sub>3</sub>Si−SiMe<sub>3</sub> + I<sub>2</sub> → 2 SiMe<sub>3</sub>I
==References== {{Reflist}}
Category:Carbosilanes Category:Trimethylsilyl compounds