Vinyl tributyltin

Vinyl tributyltin
	source ↗
Names
	Preferred IUPAC name Tributyl(ethenyl)stannane
	Other names Tributylvinyltin, Tributylvinylstannane
Identifiers
CAS Number	7486-35-3;
3D model (JSmol)	Interactive image;
ChemSpider	74003;
ECHA InfoCard	100.028.447
EC Number	231-291-4;
PubChem CID	81998;
UNII	2FA6XM467X Y;
CompTox Dashboard (EPA)	DTXSID40225836;
	InChI InChI=1S/3C4H9.C2H3.Sn/c31-3-4-2;1-2;/h31,3-4H2,2H3;1H,2H2; Key: QIWRFOJWQSSRJZ-UHFFFAOYSA-N;
	SMILES CCCC[Sn](CCCC)(CCCC)C=C;
Properties
Chemical formula	C14H30Sn
Molar mass	317.104 g·mol−1
Appearance	colorless oil
Density	1.081 g/cm3
Boiling point	104–106 °C (219–223 °F; 377–379 K) 3.5 mmHg
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Infobox references

Vinyl tributyltin is an organotin compound with the formula Bu₃SnCH=CH₂ (Bu = butyl). It is used as a source of vinyl anion equivalent in Stille coupling reactions.¹² As a source of vinyltin reagents, early work used vinyl trimethyltin,³ but trimethyltin compounds are avoided nowadays owing to their toxicity.

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

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.
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.
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.
Dietmar Seyferth (1959). "Di-n-butyldivinyltin". Org. Synth. 39: 10. doi:10.15227/orgsyn.039.0010.

[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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