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Vinyl tributyltin

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Vinyl tributyltin
Names
Preferred IUPAC name Tributyl(ethenyl)stannane
Other names Tributylvinyltin, Tributylvinylstannane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.028.447 Edit this at Wikidata
EC Number
  • 231-291-4
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/3C4H9.C2H3.Sn/c3*1-3-4-2;1-2;/h3*1,3-4H2,2H3;1H,2H2;Key: QIWRFOJWQSSRJZ-UHFFFAOYSA-N
SMILES
  • CCCC(CCCC)(CCCC)C=C
Properties
Chemical formula C14H30Sn
Molar mass 317.104 g·mol
Appearance colorless oil
Density 1.081 g/cm
Melting point 95 °C (203 °F; 368 K)
Boiling point 253–254 °C (487–489 °F; 526–527 K) 1.5 Torr
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
Hazard statements H226, H301, H312, H315, H319, H372, H410
Precautionary statements P210, P233, P240, P241, P242, P243, P260, P264, P270, P273, P280, P301+P310, P302+P352, P303+P361+P353, P305+P351+P338, P312, P314, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P391, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Vinyl tributyltin is an organotin compound with the formula Bu3SnCH=CH2 (Bu = butyl). It is a white, air-stable solid. It is used as a source of vinyl anion equivalent in Stille coupling reactions. As a source of vinyltin reagents, early work used vinyl trimethyltin, but trimethyltin compounds are avoided nowadays owing to their toxicity.

Preparation

The compound is prepared by the reaction of vinylmagnesium bromide with tributyltin chloride. It can be synthesized in the laboratory by hydrostannylation of acetylene with tributyltin hydride. It is commercially available.

References

  1. Farina, Vittorio; Krishnan, Bala (1991). "Large Rate Accelerations in the Stille Reaction with Tri-2-furylphosphine and Triphenylarsine as Palladium Ligands: Mechanistic and synthetic implications". Journal of the American Chemical Society. 113 (25): 9585–9595. doi:10.1021/ja00025a025.
  2. Littke, Adam F.; Schwarz, Lothar; Fu, Gregory C. (2002). "Pd/P(t-Bu)3: A Mild and General Catalyst for Stille Reactions of Aryl Chlorides and Aryl Bromides". Journal of the American Chemical Society. 124 (22): 6343–6348. doi:10.1021/ja020012f. PMID 12033863.
  3. Scott, William J.; Crisp, G. T.; Stille, J. K. (1990). "Palladium-Catalyzed Coupling of Vinyl Triflates With Organostannanes: 4-tert-Butyl-1-vinylcyclohexene and 1-(4-tert-Butylcyclohexen-1-yl)-2-propen-1-one". Organic Syntheses. 68: 116. doi:10.15227/orgsyn.068.0116.
  4. Dietmar Seyferth (1959). "Di-n-butyldivinyltin". Org. Synth. 39: 10. doi:10.15227/orgsyn.039.0010.
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