Tris(phenylthio)methane

Abstract

[4832-52-4] C19H16S3 (MW 340.56) InChI = 1S/C19H16S3/c1-4-10-16(11-5-1)20-19(21-17-12-6-2-7-13-17)22-18-14-8-3-9-15-18/h1-15,19H InChIKey = YOQHDHPBEXTHCP-UHFFFAOYSA-N (precursor to tris(phenylthio)methyllithium, used for nucleophilic carboxylation;1 electrophilic formylating agent for aromatic compounds2 and diazo esters3) Physical Data: mp 40–41 °C. Solubility: freely sol most organic solvents; usually used in THF, methylene chloride, or ether. Form Supplied in: off-white to pale yellow solid, typically 97–99% pure; commercially available. Analysis of Reagent Purity: the NMR spectrum will establish the absence of ethyl formate, the usual precursor to the reagent. Residual thiophenol can be removed by washing an ethereal solution of the reagent with 1 N NaOH followed by standing under high vacuum. Handling, Storage, and Precautions: is stable indefinitely if stored at ambient temperatures in tightly sealed containers to exclude moisture, which promotes hydrolysis to thiophenol and formic acid. The presence of residual thiophenol mandates that the reagent be handled in a fume hood to avoid inhalation of dust and that skin contact be avoided. Preparative Methods: conveniently prepared by the reaction of thiophenol with formic acid or methyl orthoformate, catalyzed by dry HCl and boron trifluoride etherate, respectively.7