Bis(trimethylsilyl)sulfide
sulfide.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 | ||
| PubChem CID |
|||
| 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] | ||
| Refractive index (nD) |
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 | |||
| 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). | |||
 verify (what is  ?) | |||
| Infobox references | |||
sulfide-3D-balls.png)
sulfide-3D-spacefill.png)
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]
Safety
((CH3)3Si)2S reacts exothermically with water, releasing toxic H2S.
References
- ↑ mastersearch.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet
- 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
- ↑ 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.
- ↑ So, J.-H.; Boudjouk, P. (1992). "Hexamethyldisilathiane". In Russell, N. G. Inorganic Syntheses. 29. New York: Wiley. p. 30. ISBN 0-471-54470-1. doi:10.1002/9780470132609.ch11.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.