Bis(trimethylsilyl)sulfide (original) (raw)
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Bis(trimethylsilyl)sulfide
Names | |
Preferred IUPAC name Hexamethyldisilathiane | |
Other namesTrimethyl[(trimethylsilyl)sulfanyl]silane | |
Identifiers | |
CAS Number | 3385-94-2 Y |
3D model (JSmol) | Interactive imageInteractive image |
Beilstein Reference | 1698358 |
ChemSpider | 69371 Y |
ECHA InfoCard | 100.020.184 |
EC Number | 222-201-4 |
PubChem CID | 76920 |
UNII | AZ6L5QJY5H Y |
UN number | 1993 |
CompTox Dashboard (EPA) | DTXSID2063006 |
InChI InChI=1S/C6H18SSi2/c1-8(2,3)7-9(4,5)6/h1-6H3 YKey: RLECCBFNWDXKPK-UHFFFAOYSA-N YInChI=1/C6H18SSi2/c1-8(2,3)7-9(4,5)6/h1-6H3Key: RLECCBFNWDXKPK-UHFFFAOYAN | |
SMILES C[Si](C)(C)S[Si](C)(C)CS([Si](C)(C)C)[Si](C)(C)C | |
Properties | |
Chemical formula | 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) |
Solubility in water | hydrolyzes |
Solubility in other solvents | ethers such as THF and arenes such as toluene[1] |
Refractive index (_n_D) | 1.4586 |
Structure | |
Dipole moment | 1.85 D |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | Toxic |
GHS labelling: | |
Pictograms | |
Signal word | Danger |
Hazard statements | H226, H301, H311, H331[2] |
Precautionary statements | P261, P280, P301+P310, P311[2] |
NFPA 704 (fire diamond) | 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 [77 °F], 100 kPa). Y verify (what is YN ?) 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 "S2−" in chemical synthesis.[3]
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
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]
((CH3)3Si)2S reacts exothermically with water, releasing toxic H2S.
- ^ mastersearch.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet
- ^ a b Product catalog sigmaaldrich.com [_dead link_]
- ^ Matulenko, M. A. (2004). "Bis(trimethylsilyl) Sulfide". Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette), J. Wiley & Sons, New York. 1: 5. doi:10.1002/047084289X. hdl:10261/236866. ISBN 9780471936237.
- ^ 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.
- ^ 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 (3): 305–309. doi:10.1002/anie.200352351. PMID 14705083.