Tributyl-1,2-propadien-1-yl-stannane

[53915-69-8] C15H30Sn (MW 329.11) InChI = 1S/3C4H9.C3H3.Sn/c3*1-3-4-2;1-3-2;/h3*1,3-4H2,2H3;1H,2H2; InChIKey = QAHMAFPUBBWUIS-UHFFFAOYSA-N (three-carbon nucleophilic component in addition and cross-coupling reactions) Physical Data: bp 265 °C (760 mmHg); 89 °C (0.1 mmHg); d 1.107 g cm−3. Solubility: sol in dichloromethane, diethyl ether, toluene, THF, and acetonitrile. Form Supplied in: commercially available colorless liquid, 80–85% purity. Major impurity in the form of tributyl(prop-2-ynyl) stannane. Analysis of Reagent Purity: 1H NMR. Preparative Methods: through the addition of tributyltin chloride to a solution of propargylmagnesium bromide in diethyl ether (eq 1).2, 3 This gives a 95:5 mixture of tributyl-1,2-propadienylstannane and tributyl(prop-2-ynyl) stannane. (1) Other preparative methods have been developed that give exclusively the allenic compound.4-6 Purification: distillation under reduced pressure. Handling, Storage, and Precautions: must be stored below −18 °C. The compound is moisture sensitive. Tributyl-1,2-propadien-1-yl-stannane is a very toxic compound that should be handled in a well-ventilated fume hood wearing gloves and protective clothing. Harmful to aquatic organisms, prevent exposure to the environment.