Bis(trimethylsilyl)sulfide

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
Bis(trimethylsilyl)sulfide
Stereo structural formula of bis(trimethylsilyl)sulfide
Stereo structural formula of bis(trimethylsilyl)sulfide
Names
Preferred IUPAC name
Hexamethyldisilathiane
Other names
Trimethyl[(trimethylsilyl)sulfanyl]silane
Identifiers
3D model (JSmol)
1698358
ChemSpider
ECHA InfoCard 100.020.184 Edit this at Wikidata
EC Number
  • 222-201-4
UNII
UN number 1993
  • InChI=1S/C6H18SSi2/c1-8(2,3)7-9(4,5)6/h1-6H3 checkY
    Key: RLECCBFNWDXKPK-UHFFFAOYSA-N checkY
  • InChI=1/C6H18SSi2/c1-8(2,3)7-9(4,5)6/h1-6H3
    Key: RLECCBFNWDXKPK-UHFFFAOYAN
  • C[Si](C)(C)S[Si](C)(C)C
  • S([Si](C)(C)C)[Si](C)(C)C
Properties
C6H18SSi2
Molar mass 178.44 g·mol−1
Appearance colourless liquid with foul odor
Density 0.846 g cm−3
Boiling point 163 Â°C (325 Â°F; 436 K)
hydrolyzes
Solubility in other solvents ethers such as THF
and arenes such as toluene
[1]
1.4586
Structure
1.85 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
GHS labelling:
GHS06: Toxic GHS02: Flammable
Danger
H226, H301, H311, H331[2]
P261, P280, P301+P310, P311[2]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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 Â°C [77 Â°F], 100 kPa).
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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

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