Methyl 4-bromocrotonate: Properties and Safety Guidelines

Definition of Methyl 4-Bromocrotonate

Methyl 4-bromocrotonate, with the English name: Methyl 4-bromocrotonate, CAS: 1117-71-1, and Methyl 4 bromocrotonate formula : C5H7BrO2, is a useful synthetic intermediate mainly utilized in organic synthesis, particularly in the preparation of substituted crotonates. Methyl 4-bromocrotonate is used to synthesize irreversible inhibitors of EGFR and HER-2 tyrosine kinases, which exhibit enhanced antitumor activity.

Properties of Methyl 4-Bromocrotonate

• Appearance and Character: Clear slightly yellow liquid
• Molecular Formula: C5H7BrO2
• Molecular Weight: 179.01 g/mol
• Density: 1.522 g/mL at 25 °C (lit.)
• Boiling Point: 83-85 °C13 mm Hg (lit.)
• Flash Point: 197 °F
• Solubility: Soluble in dichloromethane, chloroform, and ethanol
• Acidity Coefficient (pKa): 2.32±0.10 (predicted)
• Refractive Index: n20/D 1.501
• Stability: Decomposes when stored, especially when exposed to light or heat
• Storage Conditions: 2-8°C
• Vapor Pressure: 0.358 mmHg at 25°C

Methyl 4 bromocrotonate structure

The molecular formula of Methyl 4-bromocrotonate is C5H7BrO2, with the chemical structure BrCH2CH=CHCO2CH3. This compound contains a bromine atom, a double bond, an ester group, and a methyl group, classified as an α,β-unsaturated ester. It is characterized by a carbon-carbon double bond adjacent to a carbonyl (C=O) group. The structure of Methyl 4-bromocrotonate is crucial due to its conjugated system, which includes alternating carbon-carbon double and single bonds, allowing for electron delocalization and influencing its reactivity. The presence of the bromine atom makes it a halogenated compound.

Methyl 4 bromocrotonate structure

Methyl 4 bromocrotonate preparation

Methyl 4-bromocrotonate is typically synthesized by brominating methyl crotonate. N-Bromosuccinimide (NBS) is a common brominating agent for this reaction. It is important to note that the synthesis of this compound can be hazardous if not conducted under proper conditions and safety precautions. Always wear appropriate personal protective equipment (PPE) and carry out reactions in a well-ventilated fume hood.

Safety and Handling

Hazards

Ingesting this substance may be harmful and may cause corrosion to metals. It can cause severe skin burns and eye damage and may pose hazards to terrestrial vertebrates.

Safety Precautions

Store only in the original container. Do not breathe dust/fume/gas/mist/vapors/spray. Wash thoroughly after handling. Do not eat, drink, or smoke when using this product. Wear protective gloves/protective clothing/eye protection/face protection.

Safe Storage Conditions, Including Any Incompatibilities

Store in a cool place. Keep the container tightly closed and stored in a dry, well-ventilated place. Opened containers must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature is 2-8°C.

First Aid Measures

If ingested: If you feel unwell, call a poison center or doctor. Rinse mouth. Do not induce vomiting.

If on skin (or hair): Immediately take off all contaminated clothing. Rinse skin/shower with water.

If inhaled: Move 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.

References

• PubChem: Methyl 4-bromocrotonate
• https://es.wikipedia.org/wiki/Wikipedia:Portada
• Prempree P, Radviroongit S, Thebtaranonth Y. Reaction of methyl 4-bromocrotonate with lithium ester enolates: direct SN2 displacement vs. Michael-initiated ring closure[J]. The Journal of Organic Chemistry, 1983, 48(20): 3553-3556.