Hexamethyldisilane

Quality 0.50 · 2 views · Updated 2 months ago

title: "Hexamethyldisilane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["carbosilanes", "trimethylsilyl-compounds"] topic_path: "general/carbosilanes" source: "https://en.wikipedia.org/wiki/Hexamethyldisilane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 418735081 | ImageFile = Hexamethyldisilane.svg | ImageFile_Ref = | ImageSize = 160 | ImageName = Skeletal formula of hexamethyldisilane | ImageFileL1 = Hexamethyldisilane-3D-balls.png | ImageFileL1_Ref = | ImageAltL1 = Ball-and-stick model | ImageFileR1 = Hexamethyldisilane-3D-spacefill.png | ImageFileR1_Ref = | ImageAltR1 = Space-filling model | PIN = Hexamethyldisilane |Section1={{Chembox Identifiers | CASNo = 1450-14-2 | CASNo_Ref = | UNII_Ref = | UNII = A7HH2E9DUB | PubChem = 74057 | ChemSpiderID = 66675 | ChemSpiderID_Ref = | EINECS = 215-911-0 | UNNumber = 1993 | RTECS = JM9170000 | Beilstein = 1633463 | SMILES = CSi(C)Si(C)C | StdInChI = 1S/C6H18Si2/c1-7(2,3)8(4,5)6/h1-6H3 | StdInChI_Ref = | StdInChIKey = NEXSMEBSBIABKL-UHFFFAOYSA-N | StdInChIKey_Ref = |Section2={{Chembox Properties | Formula = Si2C6H18 | MolarMass = 146.39 g mol−1 | Appearance = Colourless liquid | Density = 0.715 g/cm3 | MeltingPtK = 287 | BoilingPtK = 386 | RefractIndex = 1.422 |Section3={{Chembox Thermochemistry | Entropy = 255.89 J K−1 mol−1 (at 22.52 °C) |Section4={{Chembox Hazards | GHSPictograms = | GHSSignalWord = DANGER | HPhrases = | PPhrases = | FlashPtC = 11 |Section5={{Chembox Related | OtherFunction_label = alkylsilanes | OtherFunction = Tetramethylsilane

Triethylsilane

Hexamethyldisilane (TMS2) is the organosilicon compound with the formula Si2(CH3)6, abbreviated Si2Me6. It is a colourless liquid, soluble in organic solvents.

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: : With an excess of the reductant, the alkali metal silyl derivative is produced: :

The Si-Si bond in hexamethyldisilane is cleaved by strong nucleophiles and electrophiles. Alkyl lithium compounds react as follows: :Si2Me6 + RLi → RSiMe3 + LiSiMe3

Iodine gives trimethylsilyl iodide. :Me3Si−SiMe3 + I2 → 2 SiMe3I

References

References

  1. Tamejiro Hiyama, Manabu Kuroboshi, "Hexamethyldisilane" Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons. {{doi. 10.1002/047084289X.rh015
  2. (1988). "Efficient formation and cleavage of disilanes by potassium-graphite. Silylation with silyl metal reagents". Journal of Organometallic Chemistry.
  3. (1982). "Iodotrimethylsilane—a versatile synthetic reagent". [[Tetrahedron (journal).

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

carbosilanestrimethylsilyl-compounds