Bis(trimethylsilyl)sulfide
{{Chembox
| Watchedfields = changed
| verifiedrevid = 401708703
| ImageFile = S(tms)2.svg
| ImageSize = 240px
| ImageName = Stereo structural formula of bis(trimethylsilyl)sulfide
| ImageFileL1 = Bis(trimethylsilyl)sulfide-3D-balls.png
| ImageFileR1 = Bis(trimethylsilyl)sulfide-3D-spacefill.png
| PIN = Hexamethyldisilathiane
| OtherNames = Trimethyl[(trimethylsilyl)sulfanyl]silane
|Section1={{Chembox Identifiers
| CASNo = 3385-94-2
| CASNo_Ref = {{cascite|correct|??}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = AZ6L5QJY5H
| PubChem = 76920
| ChemSpiderID = 69371
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 222-201-4
| UNNumber = 1993
| SMILES = C[Si](C)(C)S[Si](C)(C)C
| SMILES1 = S([Si](C)(C)C)[Si](C)(C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H18SSi2/c1-8(2,3)7-9(4,5)6/h1-6H3
| InChI = 1/C6H18SSi2/c1-8(2,3)7-9(4,5)6/h1-6H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RLECCBFNWDXKPK-UHFFFAOYSA-N
| InChIKey = RLECCBFNWDXKPK-UHFFFAOYAN
| Beilstein = 1698358}}
|Section2={{Chembox Properties
| C=6 | H=18 | Si=2 | S=1
| Appearance = colourless liquid with foul odor
| Density = 0.846 g cm−3
| Solubility = hydrolyzes
| Solvent = other solvents
| SolubleOther = ethers such as THF
and arenes such as toluene
mastersearch.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet
| BoilingPtC = 163
| RefractIndex = 1.4586}}
|Section3={{Chembox Structure
| Dipole = 1.85 D
}}
|Section7={{Chembox Hazards
| ExternalSDS = [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 "External MSDS"]
| MainHazards = Toxic
| GHSPictograms = {{GHS skull and crossbones}} {{GHS flame}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|226|331|311|301||}}[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 Product catalog] sigmaaldrich.com {{dead link|date=March 2024}}
| PPhrases = {{P-phrases|261|280|301+310|311}}
| NFPA-H=2|NFPA-F=3|NFPA-R=0|NFPA-S=
}}
|Section8={{Chembox Related
}}
}}
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 |year =2004 |doi = 10.1002/047084289X |volume=1 |pages=5|hdl=10261/236866 |isbn=9780471936237|url=https://hal.archives-ouvertes.fr/hal-02922790|hdl-access=free }}
Synthesis
The reagent is prepared by treating trimethylsilyl chloride with anhydrous sodium sulfide:{{cite book |author1=So, J.-H. |author2=Boudjouk, P. | chapter = Hexamethyldisilathiane | title = Inorganic Syntheses | editor = Russell, N. G. | year = 1992 | volume = 29 | isbn = 0-471-54470-1 | doi = 10.1002/9780470132609.ch11 | page = 30 | publisher = Wiley | location = New York}}
: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.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. 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.{{cite journal| title = Synthetic Applications of Bis(trimethylsilyl)sulfide: Part II. Synthesis of Aromatic and Heteroaromatic o-Azido-Thioaldehydes|author1=A. Capperucci |author2=A. Degl'Innocenti |author3=P. Scafato |author4=P. Spagnolo | journal = Chemistry Letters| volume = 24| pages = 147| year = 1995| doi = 10.1246/cl.1995.147| issue = 2}}{{cite journal| title = Some Recent Synthetic Routes to Thioketones and Thioaldehydes|author1=W. M. McGregor |author2=D. C. Sherrington | journal = Chemical Society Reviews| volume = 22| pages = 199–204| year = 1993| doi = 10.1039/CS9932200199| issue = 3}}
Image:ASUTAJ = CCDB code. Ag-S nanocrystal as described in doi 10.1002SLASHanie.200352351.png
Safety
((CH3)3Si)2S reacts exothermically with water, releasing toxic H2S.