Preparation of (+)- and (-)-2,3-Dibromo-1-propanols

Article abstract of DOI:10.1021/je00030a033

The enantiomers of 2,3-dibromo-1-propanol were obtained by diazotization of the diastereomeric d-tartrate salts of 2,3-dibromopropylamine.The products of the reaction contained approximately 13percent of the secondary alcohol 1,3-dibromo-2-propanol which was separated by either column chromatography on silica gel or preparative GLC to obtain the primary alcohols (+)-2,3-dibromo-1-propanol (<α>²⁶_D +13.8 deg) and (-)-2,3-dibromo-1-propanol (<α>²⁴_D -12.8 deg).NMR and EI mass spectra of the primary and secondary dibromopropanols clearly distinguished the structuralisomers from one another.The optical isomers will be used to examine possible stereoselective differences in mutagenic potency, since 2,3-dibromo-1-propanol is a mutagenic metabolite of the potent mutagen and carcinogen tris(2,3-dibromopropyl) phosphate.