| Revision as of 14:15, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Saving copy of the {{chembox}} taken from revid 450303181 of page Trimethylsilyl_cyanide for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 17:02, 5 July 2023 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,994 edits →Structure: tms-NC-M |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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|Watchedfields = changed |
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| verifiedrevid = 412009295 |
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|verifiedrevid = 470615759 |
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| ImageFileL1 = Trimethylsilyl-cyanide-skeletal.png |
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|ImageFileL1 = Trimethylsilyl-cyanide-skeletal.png |
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| ImageSizeL1 = 120px |
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|ImageSizeL1 = 120px |
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| ImageFileR1 = Trimethylsilyl-cyanide-3D-vdW.png |
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|ImageFileR1 = Trimethylsilyl-cyanide-3D-vdW.png |
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| ImageSizeR1 = 120px |
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|ImageSizeR1 = 120px |
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|PIN = Trimethylsilanecarbonitrile |
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| IUPACName = trimethylsilylformonitrile |
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| OtherNames = Cyanotrimethylsilane; TMS cyanide; Trimethylsilylnitrile; Trimethylsilanecarbonitrile' Trimethylsilylcarbonitrile |
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|OtherNames = Cyanotrimethylsilane; TMS cyanide; Trimethylsilylnitrile; Trimethylsilylcarbonitrile; Trimethylsilylformonitrile |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| Abbreviations = TMSCN |
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|Abbreviations = TMSCN |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 74110 |
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|ChemSpiderID = 74110 |
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| InChI = 1/C4H9NSi/c1-6(2,3)4-5/h1-3H3 |
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|InChI = 1/C4H9NSi/c1-6(2,3)4-5/h1-3H3 |
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| InChIKey = LEIMLDGFXIOXMT-UHFFFAOYAM |
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|InChIKey = LEIMLDGFXIOXMT-UHFFFAOYAM |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C4H9NSi/c1-6(2,3)4-5/h1-3H3 |
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|StdInChI = 1S/C4H9NSi/c1-6(2,3)4-5/h1-3H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = LEIMLDGFXIOXMT-UHFFFAOYSA-N |
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|StdInChIKey = LEIMLDGFXIOXMT-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 7677-24-9 |
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|CASNo = 7677-24-9 |
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|EC_number = 231-657-3 |
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| EINECS = |
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| PubChem = 82115 |
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|PubChem = 82115 |
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| SMILES = C(C)(C)C#N |
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|SMILES = C(C)(C)C#N |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| InChI = |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| RTECS = |
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| MeSHName = |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = |
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| ATCCode = }} |
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| Section2 = {{Chembox Properties |
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| C=4|H=9|Si=1|N=1 |
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| Appearance = |
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| Density = 0.793 g/mL at 20 °C |
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| MeltingPtCL = 8 |
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| MeltingPtCH = 11 |
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| Melting_notes = |
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| BoilingPtCL = 114 |
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| BoilingPtCH = 117 |
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| Boiling_notes = |
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| Solubility = organic solvents |
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| SolubleOther = reacts with water |
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| Solvent = |
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| pKa = |
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| pKb = |
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| IsoelectricPt = |
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| SpecRotation = |
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| RefractIndex = 1.392 |
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| Viscosity = |
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| Dipole = }} |
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| Section3 = {{Chembox Structure |
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| CrystalStruct = |
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| Coordination = |
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| MolShape = |
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| Dipole = }} |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = |
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| EUClass = |
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| NFPA-H = |
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| NFPA-F = |
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| NFPA-R = |
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| NFPA-O = |
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| RPhrases = {{R11}} {{R26/27/28}} {{R29}} |
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| SPhrases = {{S16}} {{S36/37/39}} {{S45}} |
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| RSPhrases = |
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| FlashPt = {{convert|1|C|F}} |
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| Autoignition = |
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| ExploLimits = |
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| PEL = }} |
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| Section8 = {{Chembox Related |
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| OtherAnions = |
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| OtherCations = |
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| OtherFunctn = |
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| Function = |
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| OtherCpds = }} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|C=4 | H=9 | Si=1 | N=1 |
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|Density = 0.793 g/mL at 20 °C |
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|MeltingPtC = 8 to 11 |
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|BoilingPtC = 114 to 117 |
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|Solubility = hydrolyzes |
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|SolubleOther = organic solvents |
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|RefractIndex = 1.392 |
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}} |
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|Section7={{Chembox Hazards |
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|GHSPictograms = {{GHS02}}{{GHS06}}{{GHS09}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|225|300|310|330|410}} |
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|PPhrases = {{P-phrases|210|233|240|241|242|243|260|262|264|270|271|273|280|284|301+310|302+350|303+361+353|304+340|310|320|321|322|330|361|363|370+378|391|403+233|403+235|405|501}} |
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|FlashPtC = 1 |
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}} |
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|Section8={{Chembox Related |
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|OtherAnions = ] |
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}} |
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}} |
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'''Trimethylsilyl cyanide''' is the ] with the ] (CH<sub>3</sub>)<sub>3</sub>SiCN. This volatile liquid consists of a ] group, that is CN, attached to a ] group. The molecule is used in ] as the equivalent of ]. It is prepared by the reaction of ] and trimethylsilyl chloride:<ref>{{OrgSynth | author = Livinghouse, T. | title = Trimethylsilyl Cyanide: Cyanosilation of p-Benzoquinone | volume = 60 | pages = 126 | year = 1981 | doi = 10.15227/orgsyn.060.0126}}</ref><ref name=eros>{{cite book |doi=10.1002/047084289X.rc276.pub2 |chapter=Cyanotrimethylsilane |title=Encyclopedia of Reagents for Organic Synthesis |year=2011 |last1=Groutas |first1=William C. |last2=Jin |first2=Zhendong |last3=Zhang |first3=Heng |isbn=978-0471936237 }}</ref> |
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:LiCN + (CH<sub>3</sub>)<sub>3</sub>SiCl → (CH<sub>3</sub>)<sub>3</sub>SiCN + LiCl |
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==Structure== |
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The molecule exhibits the structure of a nitrile-like compound. The compound exists in a rapid equilibrium with a small amount of the ]ic ] (CH<sub>3</sub>)<sub>3</sub>SiNC.<ref>{{cite journal|first1 = M. R.|last1 = Booth|first2 = S. G.|last2 = Frankiss|title = Trimethylsilyl isocyanide|journal = ]|issue = 21|year = 1968|pages = 1347–1348|doi = 10.1039/C19680001347}}</ref> By contrast, the nearly isostructural ] does not readily isomerize to ]. The isocyanide isomer can be stabilized by ] to metals.<ref>{{cite journal |doi=10.1039/C8NJ00246K |title=Synthesis and Characterization of Cyano and Isocyano Complexes of Bis(dithiolato) Molybdenum Using Me<sub>3</sub>SiCN: A Route to a Cyanide-Bridged Multimer to a Monomer |year=2018 |last1=Bose |first1=Moumita |last2=Moula |first2=Golam |last3=Begum |first3=Ameerunisha |last4=Sarkar |first4=Sabyasachi |journal=New Journal of Chemistry |volume=42 |issue=7 |pages=5580–5592 }}</ref> |
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==Reactions== |
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Trimethylsilyl cyanide ] to give ] and ]: |
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:(CH<sub>3</sub>)<sub>3</sub>SiCN + H<sub>2</sub>O → (CH<sub>3</sub>)<sub>3</sub>SiOH + HCN |
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In its principal application, it adds across carbon-oxygen double bonds, for example in an ], to form a new carbon-carbon bond:<ref name=eros/> |
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:{{color|#0a0|RCH{{=}}O}} + (CH<sub>3</sub>)<sub>3</sub>SiC≡N → N≡C–{{color|#0a0|CHR–O}}Si(CH<sub>3</sub>)<sub>3</sub> |
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The product is an ''O''-silylated ]. |
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One use of this reagent is to convert ]-''N''-]s into 2-cyanopyridine. This transformation is best done in ] solution using dimethyl] as the activating ]. It is possible to use ] but the yields and ] of the addition of the cyano group are lower. |
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Acetone cyanohydrin can be used to reversibly generate the cyanide anion.<ref>Nazarov, N. ; Zav'yalov, I. ''J. Gen. Chem. USSR (Engl. Transl.)'' '''1954''', ''24'', 475 .</ref> |
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<span style="float:right;padding-right:50px;padding-top:30px;">'''''(4)'''''</span>] |
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==Safety== |
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Trimethylsilyl cyanide behaves equivalently to ], a potent poison.<ref name=eros/> The compound can be disposed of by using a mixture of alkali hydroxide and bleach.<ref>. Gelest. </ref> |
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==References== |
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{{Reflist}} |
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{{Cyanides}} |
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] |
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] |