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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-H302-H312-H314-H332-H335
Combustible liquid. Harmful if swallowed. Harmful in contact with skin. Causes severe skin burns and eye damage. Harmful if inhaled. May cause respiratory irritation.
Precautionary Statements: P210-P235-P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant