26928-13-2

Basic information

• Product Name: ethyl (E)-2-fluoro-3-(4-chlorophenyl)propenoate
• CAS NO: 26928-13-2
• Molecular Weight: 228.651
• Mol File: 26928-13-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: ethyl (E)-2-fluoro-3-(4-chlorophenyl)propenoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (E)-2-fluoro-3-(4-chlorophenyl)propenoate(26928-13-2)
• EPA Substance Registry System: ethyl (E)-2-fluoro-3-(4-chlorophenyl)propenoate(26928-13-2)

Safety Data

• Hazardous Substances Data: 26928-13-2(Hazardous Substances Data)

Upstream product

• 2356-16-3 ethyl(diethylphosphono)(fluoro)acetate 
• 104-88-1 4-chlorobenzaldehyde 
• 401-55-8 ethyl bromofluoroacetate 
• 7582-61-8 diethyl 2-oxo-3-fluorobutan-1,4-dioate sodium salt 
• 401-58-1 ethyl 2-fluoro-2-iodoacetate 

Relevant articles and documents

P[N(i-Bu)CH2CH2]3N: Nonionic Lewis base for promoting the room-temperature synthesis of α,β-unsaturated esters, fluorides, ketones, and nitriles using Wadsworth - Emmons phosphonates

The bicyclic triaminophosphine P(RNCH2CH2) 3N (R = i-Bu, 1c) serves as an effective promoter for the room-temperature stereoselective synthesis of α,β-unsaturated esters, fluorides, and nitriles from a wide array of aromatic, aliphatic, heterocyclic, and cyclic aldehydes and ketones, using a range of Wadsworth-Emmons (WE) phosphonates. Among the analogues of 1c [R = Me (1a), i-Pr (1b), Bn (1d)], 1a and 1b performed well, although longer reaction times were involved, and 1d led to poorer yields than 1c. Functionalities such as cyano, chloro, bromo, methoxy, amino, ester, and nitro were well tolerated. We were able to isolate and characterize (by X-ray means; see above) the reactive WE intermediate species formed from 2b and 1c.

An Expedient Stereoselective Access to (Z)-2-Fluoroalkenoates

The reaction between an aldehyde R-CHO and diethyl 2-oxo-3-fluorobutan-1,4-dioate as its sodium salt EtO2C-CO-CF-CO2Et-,Na+ mainly leads in THF to (Z)-2-fluoroalkenoates R-CH=CF-CO2Et (Z/E>/=80/20), the Z-stereoselectivity depending on the bulk of the R group.Key words: 2-Fluoroalkenoates; (Z)-stereoselective synthesis.