Bis(trimethylsilyl)sulfide
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| Bis(trimethylsilyl)sulfide | |
|---|---|
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| General | |
| Systematic name | Bis(trimethylsilyl) sulfide |
| Other names | Hexamethyldisilathiane |
| Molecular formula | C6H18S2Si |
| SMILES | ? |
| Molar mass | 178.44 g/mol |
| Appearance | colourless liquid, stench |
| CAS number | [3385-94-2] |
| Properties | |
| Density and phase | 0.846 g/cm3 |
| Solubility in water | hydrolysis |
| Other solvents | ethers arenes |
| Melting point | ? °C |
| Boiling point | 164 °C |
| Structure | |
| Dipole moment | 1.85 D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | toxic |
| NFPA 704 | |
| R/S statement | R: 10-23/24/25 S: 36/37/39-45 |
| RTECS number | 3 |
| Supplementary data page | |
| Structure and properties |
n = 1.4586 |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | 1H NMR δ 0.31 (CCl4 soln) |
| Related compounds | |
| Related compounds | B2S3, SiS2 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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.[1]
Contents |
[edit] Synthesis
The reagent is prepared by treating trimethylsilyl chloride with anhydrous sodium sulfide:[2]
- 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
[edit] Applications
(tms)2S is primarily used to convert oxides and chlorides into the corresponding sulfides.[3] 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.[4][5]
[edit] Safety
((CH3)3Si)2S reacts exothermically with water, releasing toxic H2S.
[edit] References
- ^ Matulenko, M. A. (2004.). "Bis(trimethylsilyl) Sulfide". Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette), J. Wiley & Sons, New York. DOI:10.1002/047084289..
- ^ So, J.-H.; Boudjouk, P. “Hexamethyldisilathiane” Inorganic Syntheses 1992, volume 29, page 30. ISBN 0-471-54470-1
- ^ Lee, S. C.; Holm, R. H., "Nonmolecular Metal Chalcogenide/Halide Solids and Their Molecular Cluster Analogues", Angewandte Chemie, International Edition 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: 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: 199 - 204. DOI:10.1039/CS9932200199.
