| Revision as of 01:38, 11 December 2010 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals|← Previous edit |
Latest revision as of 12:20, 13 November 2024 edit undoHeadbomb (talk | contribs)Edit filter managers, Autopatrolled, Extended confirmed users, Page movers, File movers, New page reviewers, Pending changes reviewers, Rollbackers, Template editors454,126 edits ce |
| (34 intermediate revisions by 27 users not shown) |
| Line 1: |
Line 1: |
|
{{Chembox |
|
{{Chembox |
|
|
| Watchedfields = changed |
|
| verifiedrevid = 399593236 |
|
| verifiedrevid = 401708703 |
| ⚫ |
| ImageFile = Bis(trimethylsilyl)sulfide.png |
|
|
|
| ImageFile = S(tms)2.svg |
|
| ImageSize = 200 |
|
| ImageSize = 240px |
|
| ImageName = Stereo structural formula of bis(trimethylsilyl)sulfide |
|
|
| PIN = Bis(trimethylsilyl) sulfide |
|
| ImageName = Stereo structural formula of bis(trimethylsilyl)sulfide |
|
| SystematicName = Trimethylsilane |
|
| ImageFileL1 = Bis(trimethylsilyl)sulfide-3D-balls.png |
|
⚫ |
| ImageFileR1 = Bis(trimethylsilyl)sulfide-3D-spacefill.png |
|
| OtherNames = Hexamethyldisilathiane |
|
| PIN = Hexamethyldisilathiane |
| ⚫ |
| Section1 = {{Chembox Identifiers |
|
|
|
| OtherNames = Trimethylsilane |
|
| CASNo = 3385-94-2 |
|
|
⚫ |
|Section1={{Chembox Identifiers |
| ⚫ |
| CASNo_Ref = {{cascite|correct|??}} |
|
|
| PubChem = 76920 |
|
| CASNo = 3385-94-2 |
|
| PubChem_Ref = {{Pubchemcite|correct|PubChem}} |
|
| CASNo_Ref = {{cascite|correct|??}} |
|
⚫ |
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| ChemSpiderID = 69371 |
|
|
|
| UNII = AZ6L5QJY5H |
| ⚫ |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
| EINECS = 222-201-4 |
|
| PubChem = 76920 |
|
| UNNumber = 1993 |
|
| ChemSpiderID = 69371 |
|
⚫ |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ⚫ |
| SMILES = C(C)(C)S(C)(C)C |
|
|
|
| EINECS = 222-201-4 |
| ⚫ |
| SMILES1 = S((C)(C)C)(C)(C)C |
|
|
|
| UNNumber = 1993 |
| ⚫ |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
|
⚫ |
| SMILES = C(C)(C)S(C)(C)C |
|
⚫ |
| SMILES1 = S((C)(C)C)(C)(C)C |
|
⚫ |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI = 1S/C6H18SSi2/c1-8(2,3)7-9(4,5)6/h1-6H3 |
|
| 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 |
|
| InChI = 1/C6H18SSi2/c1-8(2,3)7-9(4,5)6/h1-6H3 |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey = RLECCBFNWDXKPK-UHFFFAOYSA-N |
|
| StdInChIKey = RLECCBFNWDXKPK-UHFFFAOYSA-N |
|
| InChIKey = RLECCBFNWDXKPK-UHFFFAOYAN |
|
| InChIKey = RLECCBFNWDXKPK-UHFFFAOYAN |
|
| Beilstein = 1698358}} |
|
| Beilstein = 1698358}} |
|
| Section2 = {{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| C = 6 |
|
| C=6 | H=18 | Si=2 | S=1 |
|
⚫ |
| Appearance = colourless liquid with foul odor |
|
| H = 18 |
|
|
⚫ |
| Density = 0.846 g cm<sup>−3</sup> |
|
| Si = 2 |
|
|
⚫ |
| Solubility = hydrolyzes |
|
| S = 1 |
|
|
⚫ |
| Solvent = other solvents |
|
| ExactMass = 178.066774332 g mol<sup>-1</sup> |
|
|
|
| SolubleOther = ethers such as ]<br /> and arenes such as ]<br /><ref>mastersearch.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet</ref> |
| ⚫ |
| Appearance = colourless liquid, stench |
|
|
⚫ |
| BoilingPtC = 163 |
| ⚫ |
| Density = 0.846 g cm<sup>-3</sup> |
|
|
⚫ |
| RefractIndex = 1.4586}} |
| ⚫ |
| Solubility = hydrolysis |
|
|
⚫ |
|Section3={{Chembox Structure |
| ⚫ |
| Solvent = other solvents |
|
|
⚫ |
| Dipole = 1.85 ] |
|
| SolubleOther = ethers<br />arenes |
|
| ⚫ |
| BoilingPtC = 163 |
|
| ⚫ |
| RefractIndex = 1.4586}} |
|
| ⚫ |
| Section3 = {{Chembox Structure |
|
| ⚫ |
| Dipole = 1.85 ] |
|
|
}} |
|
}} |
|
| Section7 = {{Chembox Hazards |
|
|Section7={{Chembox Hazards |
|
|
| ExternalSDS = |
|
| ExternalMSDS = |
|
|
| MainHazards = toxic |
|
| MainHazards = Toxic |
|
|
| GHSPictograms = {{GHS skull and crossbones}} {{GHS flame}} |
|
| RPhrases = 10-23/24/25 |
|
|
|
| GHSSignalWord = '''Danger''' |
|
| SPhrases = 36/37/39-45 |
|
|
|
| HPhrases = {{H-phrases|226|331|311|301||}}<ref name="b"> sigmaaldrich.com {{dead link|date=March 2024}}</ref> |
|
|
| PPhrases = {{P-phrases|261|280|301+310|311}}<ref name="b" /> |
|
|
| NFPA-H=2|NFPA-F=3|NFPA-R=0|NFPA-S= |
|
}} |
|
}} |
|
| Section8 = {{Chembox Related |
|
|Section8={{Chembox Related |
|
| OtherCpds = B<sub>2</sub>S<sub>3</sub>, SiS<sub>2</sub> |
|
| OtherCompounds = ], ] |
|
}} |
|
}} |
|
}} |
|
}} |
|
|
|
|
|
'''Bis(trimethylsilyl) sulfide''' is the ] with the formula ((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>S. Often abbreviated (])<sub>2</sub>S, this colourless, vile-smelling liquid is a useful aprotic source of “S<sup>2−</sup>“ in chemical synthesis.<ref>{{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}}</ref> |
|
'''Bis(trimethylsilyl) sulfide''' is the ] with the formula ((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>S. Often abbreviated (])<sub>2</sub>S, this colourless, vile-smelling liquid is a useful aprotic source of "S<sup>2−</sup>" in chemical synthesis.<ref>{{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 }}</ref> |
|
|
|
|
|
==Synthesis== |
|
==Synthesis== |
|
The reagent is prepared by treating ] with ] ]:<ref>{{cite book | author = So, J.-H.; 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}}</ref> |
|
The reagent is prepared by treating ] with ] ]:<ref>{{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}}</ref> |
|
:2 (CH<sub>3</sub>)<sub>3</sub>SiCl + Na<sub>2</sub>S → ((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>S + 2 NaCl |
|
:2 (CH<sub>3</sub>)<sub>3</sub>SiCl + Na<sub>2</sub>S → ((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>S + 2 NaCl |
|
|
|
|
|
((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>S must be protected from air because it ] readily: |
|
((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>S must be protected from air because it ] readily: |
|
:((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>S + H<sub>2</sub>O → ] + H<sub>2</sub>S |
|
:((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>S + H<sub>2</sub>O → ] + H<sub>2</sub>S |
|
|
|
|
|
|
==Use in synthesis== |
|
==Applications== |
|
|
(tms)<sub>2</sub>S is primarily used to convert oxides and chlorides into the corresponding sulfides.<ref>Lee, S. C.; ], "Nonmolecular Metal Chalcogenide/Halide Solids and Their Molecular Cluster Analogues", Angewandte Chemie, International Edition English, 1990, volume 29, pages 840-856.</ref> This transformation exploits the affinity of ](IV) for oxygen and halides. An idealized reaction is: |
|
Bis(trimethylsilyl)sulfide is a reagent for the conversion of metal oxides and chlorides into the corresponding sulfides.<ref>Lee, S. C.; ], "Nonmolecular Metal Chalcogenide/Halide Solids and Their Molecular Cluster Analogues", Angewandte Chemie International Edition in English, 1990, volume 29, pages 840-856.</ref> This transformation exploits the affinity of ](IV) for oxygen and halides. An idealized reaction is: |
|
:((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>S + MO → ((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>O + MS |
|
:((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>S + MO → ((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>O + MS |
|
In a similar way, it has been used in the conversion of ]s and ]s to the corresponding ]s.<ref>{{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}}</ref><ref>{{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}}</ref> |
|
In a similar way, it has been used in the conversion of ]s and ]s to the corresponding ]s.<ref>{{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}}</ref><ref>{{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}}</ref> |
|
|
|
|
|
(CF<sub>3</sub>CO<sub>2</sub>)<sub>2</sub> and |journal=Angewandte Chemie International Edition|year=2004|volume=43|issue=3|pages=305–309|doi=10.1002/anie.200352351|pmid=14705083}}</ref>]] |
|
|
|
|
|
==Safety== |
|
==Safety== |
|
((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>S reacts exothermically with water, releasing toxic H<sub>2</sub>S. |
|
((CH<sub>3</sub>)<sub>3</sub>Si)<sub>2</sub>S reacts ]ally with water, releasing toxic H<sub>2</sub>S. |
|
|
|
|
|
==References== |
|
==References== |
|
|
{{Reflist}} |
|
<references/> |
|
|
|
|
|
|
] |
|
] |
|
|
] |
|
|
] |