Preparation of (+)- and (-)-2,3-dibromo-1-propanols
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 13% 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 ((..cap alpha..)/sup 26/ /SUB D/ + 13.8/sup 0/) AND (-)-2,3-DIBROMO-1-PROPANOL ((..cap alpha..)/sup 24/ /SUB D/ -12.8/sup 0/). NMR and EI mass spectra of the primary and secondary dibromopropanols clearly distinguished the structural isomers 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.
- Research Organization:
- Department of Medicinal Chemistry, University of Washington, Seattle, Washington 98195
- OSTI ID:
- 5484848
- Journal Information:
- J. Chem. Eng. Data; (United States), Journal Name: J. Chem. Eng. Data; (United States) Vol. 27:4; ISSN JCEAA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ADSORBENTS
ALCOHOLS
AMINES
CARCINOGENS
CHEMICAL REACTIONS
CHROMATOGRAPHY
DIAZOTIZATION
ENANTIOMORPHS
HYDROXY COMPOUNDS
ISOMERS
LIQUID COLUMN CHROMATOGRAPHY
METABOLITES
MUTAGENS
NMR SPECTRA
ORGANIC BROMINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
OXYGEN COMPOUNDS
PHOSPHATES
PHOSPHORUS COMPOUNDS
PROPANOLS
SALTS
SEPARATION PROCESSES
SILICA GEL
SPECTRA