Bis(trimethylsilyl)sulfide

Bis(trimethylsilyl)sulfide
Names
	Preferred IUPAC name Hexamethyldisilathiane
	Other names Trimethyl[(trimethylsilyl)sulfanyl]silane
Identifiers
CAS Number	3385-94-2 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	1698358
ChemSpider	69371 ;
ECHA InfoCard	100.020.184
EC Number	222-201-4;
PubChem CID	76920;
UNII	AZ6L5QJY5H ;
UN number	1993
CompTox Dashboard (EPA)	DTXSID2063006 ;
	InChI InChI=1S/C6H18SSi2/c1-8(2,3)7-9(4,5)6/h1-6H3 Key: RLECCBFNWDXKPK-UHFFFAOYSA-N ; InChI=1/C6H18SSi2/c1-8(2,3)7-9(4,5)6/h1-6H3 Key: RLECCBFNWDXKPK-UHFFFAOYAN;
	SMILES C[Si](C)(C)S[Si](C)(C)C; S([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 (nD)	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). verify (what is ?) 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

mastersearch.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet
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:10.1002/047084289X. 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.

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[1] stersearch.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet

[b-2] ttp://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:10.1002/047084289X. hdl:10261/236866. ISBN 9780471936237.

[4] 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.

[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 (3): 305–309. doi:10.1002/anie.200352351. PMID 14705083.