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Bis(trimethylsilyl)sulfide

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Bis(trimethylsilyl)sulfide
Stereo structural formula of bis(trimethylsilyl)sulfide
Names
Preferred IUPAC name Hexamethyldisilathiane
Other names Trimethylsilane
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1698358
ChemSpider
ECHA InfoCard 100.020.184 Edit this at Wikidata
EC Number
  • 222-201-4
PubChem CID
UNII
UN number 1993
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H18SSi2/c1-8(2,3)7-9(4,5)6/h1-6H3Key: RLECCBFNWDXKPK-UHFFFAOYSA-N
  • InChI=1/C6H18SSi2/c1-8(2,3)7-9(4,5)6/h1-6H3Key: RLECCBFNWDXKPK-UHFFFAOYAN
SMILES
  • C(C)(C)S(C)(C)C
  • S((C)(C)C)(C)(C)C
Properties
Chemical formula C6H18SSi2
Molar mass 178.44 g·mol
Appearance colourless liquid with foul odor
Density 0.846 g cm
Boiling point 163 °C (325 °F; 436 K)
Solubility in water hydrolyzes
Solubility in other solvents ethers such as THF
and arenes such as toluene
Refractive index (nD) 1.4586
Structure
Dipole moment 1.85 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Toxic
GHS labelling:
Pictograms GHS06: Toxic GHS02: Flammable
Signal word Danger
Hazard statements H226, H301, H311, H331
Precautionary statements P261, P280, P301+P310, P311
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 3 0
Safety data sheet (SDS) "External MSDS"
Related compounds
Related compounds B2S3, SiS2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Bis(trimethylsilyl) sulfide is the chemical compound with the formula ((CH3)3Si)2S. Often abbreviated (tms)2S, this colourless, vile-smelling liquid is a useful aprotic source of "S" in chemical synthesis.

Synthesis

The reagent is prepared by treating trimethylsilyl chloride with anhydrous sodium sulfide:

2 (CH3)3SiCl + Na2S → ((CH3)3Si)2S + 2 NaCl

((CH3)3Si)2S must be protected from air because it hydrolyzes readily:

((CH3)3Si)2S + H2O → ((CH3)3Si)2O + H2S

Use in synthesis

Bis(trimethylsilyl)sulfide is a reagent for the conversion of metal oxides and chlorides into the corresponding sulfides. This transformation exploits the affinity of silicon(IV) for oxygen and halides. An idealized reaction is:

((CH3)3Si)2S + MO → ((CH3)3Si)2O + MS

In a similar way, it has been used in the conversion of aldehydes and ketones to the corresponding thiones.

Large Ag-S cluster prepared with the use of bis(trimethylsilyl)sulfide.

Safety

((CH3)3Si)2S reacts exothermically with water, releasing toxic H2S.

References

  1. mastersearch.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet
  2. ^ Product catalog sigmaaldrich.com
  3. Matulenko, M. A. (2004). "Bis(trimethylsilyl) Sulfide". Encyclopedia of Reagents for Organic Synthesis. 1: 5. doi:10.1002/047084289X. hdl:10261/236866. ISBN 9780471936237.
  4. So, J.-H.; Boudjouk, P. (1992). "Hexamethyldisilathiane". In Russell, N. G. (ed.). Inorganic Syntheses. Vol. 29. New York: Wiley. p. 30. doi:10.1002/9780470132609.ch11. ISBN 0-471-54470-1.
  5. Lee, S. C.; Holm, R. H., "Nonmolecular Metal Chalcogenide/Halide Solids and Their Molecular Cluster Analogues", Angewandte Chemie International Edition in English, 1990, volume 29, pages 840-856.
  6. A. Capperucci; A. Degl'Innocenti; P. Scafato; P. Spagnolo (1995). "Synthetic Applications of Bis(trimethylsilyl)sulfide: Part II. Synthesis of Aromatic and Heteroaromatic o-Azido-Thioaldehydes". Chemistry Letters. 24 (2): 147. doi:10.1246/cl.1995.147.
  7. W. M. McGregor; D. C. Sherrington (1993). "Some Recent Synthetic Routes to Thioketones and Thioaldehydes". Chemical Society Reviews. 22 (3): 199–204. doi:10.1039/CS9932200199.
  8. Fenske, D.; Persau, C.; Dehnen, S.; Anson, C. E. (2004). "Syntheses and Crystal Structures of the Ag-S Cluster Compounds (CF3CO2)2 and ". Angewandte Chemie International Edition. 43 (3): 305–309. doi:10.1002/anie.200352351. PMID 14705083.
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