Bis(trimethylsilyl)sulfide

Bis(trimethylsilyl)sulfide

Chembox new
Name = Bis(trimethylsilyl)sulfide
ImageFile = Si2S.png ImageName =
IUPACName = Bis(trimethylsilyl) sulfide
OtherNames = Hexamethyldisilathiane
Section1 = Chembox Identifiers
SMILES =
CASNo = 3385-94-2
RTECS = 3
Section2 = Chembox Properties
Formula = C6H18S2Si
MolarMass = 178.44 g/mol
Appearance = colourless liquid, stench
Density = 0.846 g/cm3
Solubility = hydrolysis
Solvent = other solvents
SolubleOther = ethers
arenes
MeltingPt =
BoilingPt = 164 °C
RefractIndex = 1.4586
Section3 = Chembox Structure
Dipole = 1.85 D
Section7 = Chembox Hazards
ExternalMSDS =
MainHazards = toxic
RPhrases = 10-23/24/25
SPhrases = 36/37/39-45
Section8 = Chembox Related
OtherCpds = B2S3, SiS2

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. [cite journal|author=Matulenko, M. A. |title=Bis(trimethylsilyl) Sulfide|journal= Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette), J. Wiley & Sons, New York |year =2004. |doi = 10.1002/047084289. |volume=1 |pages=5]

ynthesis

The reagent is prepared by treating trimethylsilyl chloride with anhydrous sodium sulfide: [cite book | author = So, J.-H.; Boudjouk, P. | chapter = Hexamethyldisilathiane | title = Inorganic Syntheses | editor = Russell, N. G. | year = 1992 | volume = 29 | pages = 30 | isbn = 0-471-54470-1 | doi = 10.1002/9780470132609.ch11] :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

Applications

(tms)2S is primarily used to convert oxides and chlorides into the corresponding sulfides. [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.] This transformation exploits the affinity of silicon(IV) for oxygen and halides. An idealized reaction is::((CH3)3Si)2S + MO → ((CH3)3Si)2O + MSIn a similar way, it has been used in the conversion of aldehydes and ketones to the corresponding thiones. [cite journal| title = Synthetic Applications of Bis(trimethylsilyl)sulfide: Part II. Synthesis of Aromatic and Heteroaromatic o-Azido-Thioaldehydes| author =A. Capperucci, A. Degl’Innocenti, P. Scafato, P. Spagnolo| journal = Chemistry Letters| volume = 24| pages = 147| year = 1995| doi = 10.1246/cl.1995.147] [cite journal| title = Some Recent Synthetic Routes to Thioketones and Thioaldehydes"| author =W. M. McGregor, D. C. Sherrington| journal = Chemical Society Reviews| volume = 22| pages = 199–204| year = 1993| doi = 10.1039/CS9932200199]

afety

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

References


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