Dichlorophenylphosphine

About: Dichlorophenylphosphine is a research topic. Over the lifetime, 127 publications have been published within this topic receiving 1267 citations.

tert‐Butyl(phenyl)phosphinothioic acid

Abstract: Racemate [6002-45-5] InChI = 1S/C10H15OPS/c1-10(2,3)12(11,13)9-7-5-4-6-8-9/h4-8H,1-3H3,(H,11,13) InChIKey = ACQNBIJCKLUKMY-UHFFFAOYSA-N (S)-Enantiomer [55705-77-6] InChI = 1S/C10H15OPS/c1-10(2,3)12(11,13)9-7-5-4-6-8-9/h4-8H,1-3H3,(H,11,13)/t12-/m1/s1 InChIKey = ACQNBIJCKLUKMY-GFCCVEGCSA-N (R)-Enantiomer [54100-47-9] C10H15OPS (MW 214.26) InChI = 1S/C10H15OPS/c1-10(2,3)12(11,13)9-7-5-4-6-8-9/h4-8H,1-3H3,(H,11,13)/t12-/m0/s1 InChIKey = ACQNBIJCKLUKMY-LBPRGKRZSA-N (precursor to various optically pure phosphines, resolving agent, and chiral solvating agent) Physical Data: mp 95–96 °C. Solubility: soluble in dichloromethane, ethanol, and most organic solvents. Form Supplied in: crystalline solid. Preparative Method: racemic tert-butyl(phenyl)phosphinothioic acid is synthesized by reacting dichlorophenylphosphine with tert-butylmagnesium chloride followed by refluxing with molecular sulfur in toluene. Resolution involves treatment with (S)-(−)-α-methylbenzylamine in ether followed by collection of the crystalline, ether-insoluble (R)-(+)-acid-(S)-(−)-amine salt. If the NMR spectrum shows contamination from the diastereomeric salt, the salt is dissolved in chloroform and induced to recrystallize by addition of ether. The crude (−)-acid was recovered from the ether-soluble (S)-(−)-acid-(S)-(−)-amine salt (eq 1).1 (1) Handling, Storage, and Precautions: storage in a cool, dry place is recommended.