341972-82-5

Basic information

• Product Name: (7E,9Z)-17-bromo-heptadeca-7,9-diene
• CAS NO: 341972-82-5
• Molecular Weight: 315.337
• Mol File: 341972-82-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (7E,9Z)-17-bromo-heptadeca-7,9-diene(CAS DataBase Reference)
• NIST Chemistry Reference: (7E,9Z)-17-bromo-heptadeca-7,9-diene(341972-82-5)
• EPA Substance Registry System: (7E,9Z)-17-bromo-heptadeca-7,9-diene(341972-82-5)

Safety Data

• Hazardous Substances Data: 341972-82-5(Hazardous Substances Data)

Upstream product

• 341972-80-3 2-((E)-heptadec-10-en-8-ynyloxy)tetrahydro-pyran 
• 341972-79-0 2-((E)-11-chloro-undec-10-en-8-ynyloxy)tetrahydro-pyran 
• 10160-24-4 7-bromoheptyl alcohol 
• 10160-26-6 9-(2-tetrahydropyranyloxy)-1-nonyne 
• 10160-25-5 7-bromo-1-(2-tetrahydropyranyloxy)heptane 
• 341972-81-4 2-((8Z,10E)-heptadeca-8,10-dienyloxy)tetrahydro-pyran 

Relevant articles and documents

Sequential substitution of 1,2-dichloro-ethene: A convenient stereoselective route to (9Z,11E)-, (10E,12Z)- and (10Z,12Z)-[1-14C] conjugated linoleic acid isomers

Conjugated linoleic acid (CLA) isomers are present in human foods derived from milk or ruminant meat. To study their metabolism, (9Z,11E)-, (10E,12Z)- and (10Z,12Z)-[1-14C]-octadecadienoic acids with high radiochemical and isomeric purities (> 98%) were prepared by stereoselective multi-step syntheses involving sequential substitution of 1,2-dichloro-ethene. In the case of the (9Z,11E) isomer, a first metal-catalyzed cross-coupling reaction between (E)-1,2-dichloro-ethene and 2-non-8-ynyloxy-tetrahydro-pyran, obtained from 7-bromo-heptan-1-ol, gave a conjugated chloroenyne. A second coupling reaction with hexylmagnesium bromide provided a heptadecenynyl derivative. Stereoselective reduction of the triple bond and bromination afforded (7E,9Z)-17-bromo-heptadeca-7,9-diene. Formation of the Grignard reagent and carbonation with 14CO2 gave (9Z,11E)-[1-14C]-octadeca-9,11-dienoic acid (overall yield from 7-bromo-heptan-1-ol, 14.4%). (10E,12Z)- and (10Z,12Z)-[1-14C]-octadeca-10,12-dienoic acids were synthesized by the same methodology using 1-heptyne, 8-bromo-octan-1-ol and, respectively, (E)-1,2-dichloro-ethene and its (Z) isomer (overall yield from 8-bromo-octan-1-ol, 13.1% (10E,12Z); 17.2% (10Z,12Z)). Impurities ( 2% if present) were identified as being (E,E) CLA isomers and were removed by RP-HPLC. Metabolism studies in animal are in progress.