3-Chlorocinnamic acid Chemical Properties

Melting point:

161-164 °C(lit.)

Boiling point:

326.2±25.0 °C(Predicted)

Density 

1.332±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

4.29(at 25℃)

color 

White to Almost white

BRN 

2207378

CAS DataBase Reference

1866-38-2(CAS DataBase Reference)

NIST Chemistry Reference

m-Chlorocinnamic acid(1866-38-2)

EPA Substance Registry System

2-Propenoic acid, 3-(3-chlorophenyl)- (1866-38-2)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-24/25-36-26-37

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29163990

MSDS

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3-Chlorocinnamic acid Usage And Synthesis

Chemical Properties

white crystalline powder or crystals

Synthesis

GENERAL METHOD: Under stirring conditions, 6.76 g (65 mmol) of malonic acid was dissolved in a mixed solution of 5 mL of pyridine and 0.5 mL of piperidine. Subsequently, 3-chlorobenzaldehyde (50 mmol) was slowly added at 85°C. The reaction mixture was stirred continuously for 6 hours, during which the progress of the reaction was monitored by thin layer chromatography (TLC) to confirm complete consumption of the feedstock. Upon completion of the reaction, the mixture was cooled to room temperature and neutralized with 10% hydrochloric acid solution under ice bath conditions, at which point a white solid was observed to precipitate. The solid product was collected by filtration and washed three times with ice water to remove impurities. Finally, the target product 3-chlorocinnamic acid (2a-h) was obtained by recrystallization and purification using aqueous ethanol (1:1, v/v).

References

[1] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9152 - 9157
[2] Journal of Chemical Research, 2005, # 6, p. 364 - 365
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 7, p. 1849 - 1853
[4] Proceedings - Indian Academy of Sciences, Section A, 1941, vol. 14, p. 116 - 120
[5] Chem.Abstr., 1942, p. 1599

3-Chlorocinnamic acid (1866-38-2)Related Product Information

• Octyl 4-methoxycinnamate
• Cinnamic acid
• trans,trans-2,4-Undecadienal
• Folic acid
• Methyl cinnamate
• Stearic acid
• trans-Cinnamic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Ethyl cinnamate
• 4-Bromocinnamic acid
• Citric acid
• Ascoric Acid
• TRANS-2,4-DICHLOROCINNAMIC ACID
• 3-Nitro-4-chlorocinnamic acid
• Ethyl p-chlorocinnamate
• 2-Chlorocinnamic acid
• (E)-4-Chlorocinnamic acid ethyl ester,4-CHLOROCINNAMIC ACID ETHYL ESTER
• (E)-3-(4-Chlorophenyl)acrylic Acid