{{Chembox | ImageFile = Bu3SnCH=CH2.svg | ImageSize = | ImageAlt = | PIN = Tributyl(ethenyl)stannane | OtherNames = Tributylvinyltin, Tributylvinylstannane | Section1 = {{Chembox Identifiers | CASNo = 7486-35-3 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 2FA6XM467X | PubChem = 81998 | ChemSpiderID = 74003 | EC_number = 231-291-4 | DTXSID = DTXSID40225836 | StdInChI=1S/3C4H9.C2H3.Sn/c3*1-3-4-2;1-2;/h3*1,3-4H2,2H3;1H,2H2; | StdInChIKey = QIWRFOJWQSSRJZ-UHFFFAOYSA-N | SMILES = CCCC[Sn](CCCC)(CCCC)C=C }} | Section2 = {{Chembox Properties | C=14|H=30|Sn=1 | MolarMass = | Appearance = colorless oil | Density = 1.081 g/cm<sup>3</sup> | BoilingPtC = 104-106 | BoilingPt_notes = 3.5 mmHg | Solubility = }} | Section3 = {{Chembox Hazards | GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|226|301|312|315|319|372|410}} | PPhrases = {{P-phrases|210|233|240|241|242|243|260|264|270|273|280|301+310|302+352|303+361+353|305+351+338|312|314|321|322|330|332+313|337+313|362|363|370+378|391|403+235|405|501}} | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Vinyl tributyltin''' is an organotin compound with the formula Bu<sub>3</sub>SnCH=CH<sub>2</sub> (Bu = butyl). It is used as a source of vinyl anion equivalent in Stille coupling reactions.<ref>{{cite journal|doi=10.1021/ja00025a025|title=Large Rate Accelerations in the Stille Reaction with Tri-2-furylphosphine and Triphenylarsine as Palladium Ligands: Mechanistic and synthetic implications|journal=Journal of the American Chemical Society|volume=113|pages=9585–9595|year=1991|last1=Farina|first1=Vittorio|last2=Krishnan|first2=Bala|issue=25}}</ref><ref>{{cite journal|doi=10.1021/ja020012f|pmid=12033863|title=Pd/P(t-Bu)<sub>3</sub>: A Mild and General Catalyst for Stille Reactions of Aryl Chlorides and Aryl Bromides|journal=Journal of the American Chemical Society|volume=124|pages=6343–6348|year=2002|last1=Littke|first1=Adam F.|last2=Schwarz|first2=Lothar|last3=Fu|first3=Gregory C.|issue=22}}</ref> As a source of vinyltin reagents, early work used vinyl trimethyltin,<ref>{{cite journal|doi=10.15227/orgsyn.068.0116|title=Palladium-Catalyzed Coupling of Vinyl Triflates With Organostannanes: 4-''tert''-Butyl-1-vinylcyclohexene and 1-(4-''tert''-Butylcyclohexen-1-yl)-2-propen-1-one|first1=William J. |last1=Scott|first2=G. T. |last2=Crisp|first3=J. K.|last3=Stille| journal=Organic Syntheses|volume=68|pages=116|year=1990}}</ref> but trimethyltin compounds are avoided nowadays owing to their toxicity.{{cn|date=July 2025}}
==Preparation== The compound is prepared by the reaction of vinylmagnesium bromide with tributyltin chloride.<ref>{{cite journal|title=Di-''n''-butyldivinyltin|author=Dietmar Seyferth|journal=Org. Synth. |year=1959|volume=39|page=10|doi=10.15227/orgsyn.039.0010}}</ref> It can be synthesized in the laboratory by hydrostannylation of acetylene with tributyltin hydride. It is commercially available.
==References== {{Reflist}}
Category:Organotin compounds Category:Vinyl compounds Category:Tin(IV) compounds