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1117-71-1 - Methyl 4-bromocrotonate, tech. 85% - 4-Bromocrotonic acid methyl ester - A15582 - Alfa Aesar

A15582 Methyl 4-bromocrotonate, tech. 85%

CAS Number
1117-71-1
Synonyms
4-Bromocrotonic acid methyl ester

Size Price ($) Quantity Availability
10g 35.23
50g 123.60
250g 396.80
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Methyl 4-bromocrotonate, tech. 85%

MDL
MFCD00000246
EINECS
214-251-0

Chemical Properties

Formula
C5H7BrO2
Formula Weight
179.01
Boiling Point
83-85°/13mm
Flash Point
91°(195°F)
Density
1.524
Refractive Index
1.5010
Solubility
Slightly soluble in water.

Applications

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.

Notes

Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.

Literature References

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318-H227

Causes severe skin burns and eye damage. Causes serious eye damage. Combustible liquid.

Precautionary Statements: P210-P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. 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 IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1745755
Hazard Class
8
Packing Group
III
Harmonized Tariff Code
2916.19
TSCA
Yes
RTECS
GQ3120000

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