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It is a useful synthetic intermediate. It was used in the synthesis of irreversible inhibitors of EGFR and HER-2 tyrosine kinases with enhanced antitumor activities.
Pirote Prempree, et al. Reaction of methyl 4-bromocrotonate with lithium ester enolates: direct SN2 displacement vs. Michael-initiated ring closure.J. Org. Chem.,1983,48(20), 3553-3556.
Gary A. Koppel. γ-Alkylation of methyl 4-bromocrotonate, a vinylogous darzens reaction.Tetrahedron Lett.,1972,13(15), 1507-1509.
Undergoes a vinylogous Reformatsky reaction with carbonyl compounds, to give δ-hydroxy-ɑß-unsaturated esters: Liebigs Ann. Chem., 709, 29 (1967). Use of a Zn-Ag couple allows Reformatsky coupling to be carried out with or without allylic rearrangement depending on whether ether or THF is used as the solvent: Synth. Commun., 19, 2355 (1989). For a review of the Reformatsky synthesis, see: Synthesis, 571 (1989).
Hazard Statements: H227-H314-H318
Combustible liquid. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P260u-P201-P280a-P304+P340-P405-P501a
Obtain special instructions before use. Wear protective gloves and eye/face protection. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.