Vinyl tributyltin

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.[1][2] As a source of vinyltin reagents, early work used vinyl trimethyltin,[3] but trimethyltin compounds are avoided nowadays owing to their toxicity.

Vinyl tributyltin
Names
Preferred IUPAC name
Tributyl(ethenyl)stannane
Other names
Tributylvinyltin, Tributylvinylstannane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.028.447
EC Number
  • 231-291-4
UNII
  • InChI=1S/3C4H9.C2H3.Sn/c3*1-3-4-2;1-2;/h3*1,3-4H2,2H3;1H,2H2;
    Key: QIWRFOJWQSSRJZ-UHFFFAOYSA-N
  • CCCC[Sn](CCCC)(CCCC)C=C
Properties
C14H30Sn
Molar mass 317.104 g·mol−1
Appearance white solid
Density 1.081 g/cm3
Melting point 253–254 °C (487–489 °F; 526–527 K)
Boiling point 95 °C (203 °F; 368 K) 1.5 Torr
Hazards
GHS labelling:
GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H226, H301, H312, H315, H319, H372, H410
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 [77 °F], 100 kPa).
Infobox references

Preparation

The compound is prepared by the reaction of vinylmagnesium bromide with tributyltin chloride.[4] 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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