Diphenyl[2-(4-pyridyl)ethyl]tin hydride

Abstract

[164165-95-1] C19H19NSn (MW 380.06) InChI = 1S/C7H8N.2C6H5.Sn.H/c1-2-7-3-5-8-6-4-7;2*1-2-4-6-5-3-1;;/h3-6H,1-2H2;2*1-5H;; InChIKey = VWAJELPLCGMSTM-UHFFFAOYSA-N (reagent used in typical stannane-mediated radical reactions;1 product isolation is facilitated because the tin-containing by- products are polar and can be removed chromatographically) Physical Data: colorless oil. Solubility: soluble in benzene, toluene, ether, and other common organic solvents. Preparative Methods: can be prepared by hydrostannylation of 4-ethenylpyridine with triphenyltin hydride, replacement of one phenyl group by iodine, using 1 equiv I2 followed by reduction with lithium aluminum hydride.1 Purification: flash chromatography over silica gel, using 1:1 ethyl acetate-hexane.1 Handling, Storage, and Precautions: the compound can be stored for at least several weeks in a freezer (−10 °C) in a closed flask flushed with argon, without significant decomposition, and may be repurified, if necessary, by flash chromatography.1 The toxicity of the compound has not been studied and, as a precaution, work with this compound should be done in a fume hood and skin contact should be avoided.