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Bis(trimethylsilyl)sulfide

Bis(trimethylsilyl)sulfide
Stereo structural formula of bis(trimethylsilyl)sulfide
Bis(trimethylsilyl)sulfide-3D-balls.png
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Names
Preferred IUPAC name
Bis(trimethylsilyl) sulfide
Systematic IUPAC name
Trimethyl[(trimethylsilyl)sulfanyl]silane
Other names
Hexamethyldisilathiane
Identifiers
3D model (Jmol)
1698358
ChemSpider
ECHA InfoCard 100.020.184
EC Number 222-201-4
PubChem CID
UN number 1993
Properties
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)
hydrolyzes
Solubility in other solvents ethers such as THF
and arenes such as toluene
1.4586
Structure
1.85 D
Hazards
Main hazards Toxic
Safety data sheet "External MSDS"
GHS pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Danger
H226, H331, H311, H301
P261, P280, P301+310, P311
R-phrases R10-R23/24/25
S-phrases S36/37/39-S38-S45
NFPA 704
Flammability code 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., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
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).
YesY  (what is YesYN ?)
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.

The reagent is prepared by treating trimethylsilyl chloride with anhydrous sodium sulfide:

((CH3)3Si)2S must be protected from air because it hydrolyzes readily:

Bis(trimethylsilyl)sulfide is a reagent for the conversion of metal oxides and chlorides into the corresponding sulfides. This transformation exploits the affinity of silicon(IV) for oxygen and halides. An idealized reaction is:

In a similar way, it has been used in the conversion of aldehydes and ketones to the corresponding thiones.

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


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