Vinyl tributyltin

Vinyl tributyltin

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/c3*1-3-4-2;1-2;/h3*1,3-4H2,2H3;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
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
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 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.^{[ citation needed ]}

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.