3-CHLORO-4-FLUOROCINNAMIC ACID Chemical Properties

Melting point:

173-175°C

Boiling point:

326℃

Density 

1.420

Flash point:

151℃

storage temp. 

2-8°C

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

Hazard Note 

Harmful

HazardClass 

IRRITANT

3-CHLORO-4-FLUOROCINNAMIC ACID Usage And Synthesis

Uses

3-Chloro-4-fluorocinnamic Acid (CAS# 58537-11-4) can be used to prepare chemokine receptor modulators.

Synthesis

GENERAL METHOD: 3-chloro-4-fluorobenzaldehyde (10 mmol), malonic acid (30 mmol, 3.12 g), and piperidine (0.5 mL) were dissolved in pyridine (20 mL), and the reaction mixture was heated under reflux conditions for 4 hours. Upon completion of the reaction, the solution was cooled to room temperature and slowly poured into pre-cooled aqueous 3M HCl solution (100 mL). The precipitated white solid precipitate was collected by filtration and washed sequentially with deionized water (350 mL), 5% w/v NaHCO3 aqueous solution (20 mL) and deionized water (250 mL). The resulting solid was dried in an oven at 60 °C to constant weight. If necessary, the crude product was purified by recrystallization through EtOH/H2O mixed solvent.

References

[1] Tetrahedron, 2016, vol. 72, # 46, p. 7256 - 7262
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 409 - 416

3-CHLORO-4-FLUOROCINNAMIC ACID(155814-22-5)Related Product Information

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• 4-Chlorocinnamic acid
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• 4-FLUOROCINNAMIC ACID