Bis(trimethylsilyl)sulfide

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Bis(trimethylsilyl)sulfide
Stereo structural formula of bis(trimethylsilyl)sulfide
Bis(trimethylsilyl)sulfide-3D-balls.png
Bis(trimethylsilyl)sulfide-3D-spacefill.png
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 The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
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., gasoline Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
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[edit]

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[edit]

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[edit]

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

References[edit]

  1. ^ mastersearch.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet
  2. ^ a b 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.