Bis(trimethylsilyl)sulfide

Bis(trimethylsilyl)sulfide
Names
Preferred IUPAC name
Bis(trimethylsilyl) sulfide
Systematic IUPAC name
Trimethyl[(trimethylsilyl)sulfanyl]silane
Other names
Hexamethyldisilathiane
Identifiers
3D model (JSmol)
1698358
ChemSpider
ECHA InfoCard 100.020.184
EC Number 222-201-4
UN number 1993
Properties
C6H18SSi2
Molar mass 178.44 g·mol−1
Appearance colourless liquid with foul odor
Density 0.846 g cm−3
Boiling point 163 °C (325 °F; 436 K)
hydrolyzes
Solubility in other solvents ethers such as THF
and arenes such as toluene
[1]
1.4586
Structure
1.85 D
Hazards
Main hazards Toxic
Safety data sheet "External MSDS"
GHS pictograms
GHS signal word Danger
H226, H331, H311, H301[2]
P261, P280, P301+310, P311[2]
NFPA 704
Flammability code 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., gasolineHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
3
2
0
Related compounds
Related compounds
 B2S3, SiS2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 “S2−“ in chemical synthesis.[3]

Synthesis

The reagent is prepared by treating trimethylsilyl chloride with anhydrous sodium sulfide:[4]

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.[5] 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.[6][7]

Large Ag-S cluster prepared with the use of bis(trimethylsilyl)sulfide.[8]

Safety

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

References

  1. ↑ mastersearch.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet
  2. 1 2 http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=283134&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2F283134%3Flang%3Den
  3. ↑ Matulenko, M. A. (2004). "Bis(trimethylsilyl) Sulfide". Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette), J. Wiley & Sons, New York. 1: 5. doi:10.1002/047084289.
  4. ↑ So, J.-H.; Boudjouk, P. (1992). "Hexamethyldisilathiane". In Russell, N. G. Inorganic Syntheses. 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 [Ag70S20(SPh)28(dppm)10] (CF3CO2)2 and [Ag262S100(St-Bu)62(dppb)6]". Angewandte Chemie International Edition. 43: 305–309. doi:10.1002/anie.200352351.
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