Hexamethyldisiloxane

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

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 442989197 | ImageFile = Hmds.png | ImageFile_Ref = | ImageSize = 210 | ImageAlt = Stereo structural formula of hexamethyldisiloxane | ImageFile1 = Hexamethyldisiloxane-3D-balls.png | ImageSize1 = 190 | ImageAlt1 = Ball-and-stick model of the hexamethyldisiloxane molecule | PIN = Hexamethyldisiloxane | SystematicName = | OtherNames = {{ubl | Bis(trimethylsilyl) ether | Bis(trimethylsilyl) oxide |Section1={{Chembox Identifiers | Abbreviations = HMDSO, (TMS)2O | CASNo = 107-46-0 | CASNo_Ref = | PubChem = 24764 | ChemSpiderID = 23150 | ChemSpiderID_Ref = | UNII = D7M4659BPU | UNII_Ref = | ChEBI_Ref = | ChEBI = 78002 | EINECS = 203-492-7 | UNNumber = 1993 | MeSHName = Hexamethyldisiloxane | RTECS = JM9237000 | Beilstein = 1736258 | SMILES = O(Si(C)C)Si(C)C | StdInChI = 1S/C6H18OSi2/c1-8(2,3)7-9(4,5)6/h1-6H3 | StdInChI_Ref = | InChI = 1/C6H18OSi2/c1-8(2,3)7-9(4,5)6/h1-6H3 | StdInChIKey = UQEAIHBTYFGYIE-UHFFFAOYSA-N | StdInChIKey_Ref = | InChIKey = UQEAIHBTYFGYIE-UHFFFAOYAL}} |Section2={{Chembox Properties | C = 6 | H = 18 | O = 1 | Si = 2 | Appearance = Colourless liquid | Density = 0.764g·cm−3 | MeltingPtC = −59 | BoilingPtC = 100 to 101 | VaporPressure = 43hPa (20°C) | Solubility = 930.7±33.7ppb (23°C) | RefractIndex = 1.377 |Section3={{Chembox Hazards | MainHazards = {{ubl | Highly flammable liquid and vapour | Causes serious eye irritation | NFPA-H = 1 | NFPA-F = 4 | NFPA-R = 0 | GHSPictograms = | GHSSignalWord = Danger | HPhrases = | PPhrases = | FlashPt = −1(1)°C |Section8={{Chembox Related | OtherCompounds = {{ubl | Disiloxane | Tetramethylsilane | Dimethyl ether | Bis(trimethylsilyl)amine | Tetrakis(trimethylsilyloxy)silane

Hexamethyldisiloxane (HMDSO or MM) is an organosilicon compound with the formula O[Si(CH3)3]2, often abbreviated O[SiMe3]2. This volatile colourless liquid is used as a solvent and as a reagent in organic synthesis. It is prepared by the hydrolysis of trimethylsilyl chloride. The molecule is the protypical disiloxane and resembles a subunit of polydimethylsiloxane.

Synthesis and reactions

Hexamethyldisiloxane can be produced by the addition of trimethylsilyl chloride to purified water: :

It also results from the hydrolysis of silyl ethers and other silyl-protected functional groups. HMDSO can be converted to trimethylsilyl chloride by treatment with dimethyldichlorosilane: :

Hexamethyldisiloxane is mainly used as source of the trimethylsilyl functional group (-Si(CH3)3) in organic synthesis. For example, in the presence of acid catalyst, it converts alcohols and carboxylic acids into the silyl ethers and silyl esters, respectively.

It reacts with rhenium(VII) oxide to give a siloxide: : Re2O7 + O[SiMe3]2 → 2 O3ReOSiMe3

HMDSO is a precursor to trimethylsilyl iodide: :

Solvent-related uses

HMDSO is an effective solvent for thiations using phosphorus pentasulfide.

It is used occasionally as an internal standard for 1H NMR spectroscopy. It is more easily handled since it is less volatile than the usual standard tetramethylsilane but still displays only a singlet near 0ppm.

HMDSO has even poorer solvating power than alkanes. It is therefore sometimes employed to crystallise highly lipophilic compounds.

Other

It is used in liquid bandages (spray-on plasters) such as Cavilon spray, to protect damaged skin from irritation from other bodily fluids. It is also used to soften and remove adhesive residues left by medical tape and bandages, without causing further skin irritation.

HMDSO is being studied for making low-k dielectric materials for the semiconductor industries by plasma-enhanced chemical vapour deposition (PECVD).

HMDSO has been used as a reporter molecule to measure tissue oxygen tension (pO). HMDSO is highly hydrophobic and exhibits high gas solubility, and hence strong nuclear magnetic resonance spin lattice relaxation rate (R1) response to changes in pO. Molecular symmetry provides a single NMR signal. Following direct injection into tissues it has been used to generate maps of tumour and muscle oxygenation dynamics with respect to hyperoxic gas breathing challenge.

References

References

  1. {{GESTIS
  2. (1996). "Aqueous solubility of permethylsiloxanes (silicones)". [[Environmental Toxicology and Chemistry]].
  3. (2008). "Encyclopedia of Reagents for Organic Synthesis".
  4. Röshe, L.; John, P.; Reitmeier, R. “Organic Silicon Compounds” ''Ullmann’s Encyclopedia of Industrial Chemistry''. John Wiley and Sons: San Francisco, 2003. {{doi. 10.1002/14356007.a24_021.
  5. Schmidt, M.; Schmidbaur, H., "Trimethylsilyl perrhenate", Inorg. Synth. 1967, 9, 149-151. {{doi. 10.1002/9780470132401.ch40
  6. Michael E. Jung, Mark A. Lyster. (1979). "Cleavage of Methyl Ethers with Iodotrimethylsilane: Cyclohexanol from Cyclohexyl Methyl Ether". Organic Syntheses.
  7. Spencer Knapp, Richard A. Huhn, Benjamin Amorelli. (2007). "Thionation: GlcNAc-Thiazoline Triacetate". Organic Syntheses.
  8. (2014). "Synthesis, Spectroscopy, and Hydrogen/Deuterium Exchange in High-Spin Iron(II) Hydride Complexes". Inorganic Chemistry.
  9. Kodibagkar VD, Cui W, Merritt ME, Mason RP. A novel 1H NMR approach to quantitative tissue oximetry using hexamethyldisiloxane. Magn Reson Med 2006;55:743–748 and Kodibagkar VD, Wang X, Pacheco-Torres J, Gulaka P, Mason RP. Proton Imaging of Siloxanes to map Tissue Oxygenation Levels (PISTOL): a tool for quantitative tissue oximetry. NMRBiomed 2008;21:899–907.

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siloxanestrimethylsilyl-compounds