126275-39-6

Basic information

• Product Name: (2Z,4Z)-2,4-Difluoro-5-phenyl-penta-2,4-dienoic acid ethyl ester
• CAS NO: 126275-39-6
• Molecular Weight: 238.234
• Mol File: 126275-39-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2Z,4Z)-2,4-Difluoro-5-phenyl-penta-2,4-dienoic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z,4Z)-2,4-Difluoro-5-phenyl-penta-2,4-dienoic acid ethyl ester(126275-39-6)
• EPA Substance Registry System: (2Z,4Z)-2,4-Difluoro-5-phenyl-penta-2,4-dienoic acid ethyl ester(126275-39-6)

Safety Data

• Hazardous Substances Data: 126275-39-6(Hazardous Substances Data)

Upstream product

• 136-60-7 benzoic acid, butyl ester 
• 20397-59-5 ethyl (Z)-2-fluoro-3-phenylacrylate 
• 126300-18-3 ethyl 2-(diethoxyphosphoryl)-2-fluoroacetate lithium salt 
• 2356-16-3 ethyl(diethylphosphono)(fluoro)acetate 

Relevant articles and documents

Reduction-Olefination of Esters: A New and Efficient Synthesis of α-Fluoro α,β-Unsaturated Esters

A reduction-olefination sequence has been used to convert esters to α-fluoro α,β-unsaturated esters.In the presence of diisobutylaluminum hydride, esters are reduced to aldehydes that react in situ with -Li+ to form the title compounds in good yield with high stereoselectivity.The reaction is applicable to aliphatic, aromatic, cyclic, unsaturated, perfluorinated, and partially fluorinated esters.The E/Z ratio of unsaturated esters formed in the reaction varies with the cations present in the reaction mixture.Solvents have very little influence on stereochemistry.The sequential transformation of PhC(O)OBun to (E)-PhCH=CFC(O)OEt and then to (E,E)-PhCH=CFCH=CFC(O)OEt illustrates the scope of this methodology, which introduces a fluorine atom adjacent to an ester functionality with concomitant elongation of the chain by two carbon atoms.