3-Cyanocinnamic acid Chemical Properties

Boiling point:

357.9±25.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.20±0.10(Predicted)

Appearance

White to off-white Solid

Safety Information

HS Code 

2918290090

3-Cyanocinnamic acid Usage And Synthesis

Uses

3-Cyanocinnamic Acid was used to synthesize triazoles with antifungal activities. It was also used to prepare aminocyclohexylethyl-substituted methylsulfonyloxy and methylsulfonyl tetrahydrobenzazepines as dopamine receptor antagonists and antipsychotics.

Synthesis

GENERAL METHOD: 3-cyanobenzaldehyde (11a) or 4-cyanobenzaldehyde (11b) (15 mmol) and malonic acid (30 mmol) were dissolved in pyridine (30 mL). Piperidine (3.0 mmol) was added to the solution and the reaction mixture was subsequently heated to reflux at 100 °C for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and acidified by slow addition of 5 M hydrochloric acid solution (25 mL). The precipitated white precipitate was collected by filtration, washed well with water and dried to give the target products (E)-3-cyanocinnamic acid (12a) or (E)-4-cyanocinnamic acid (12b) in 81% and 78% yields, respectively.

References

[1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5162 - 5174
[2] Journal of the American Chemical Society, 1948, vol. 70, p. 1560
[3] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2021 - 2034
[4] Patent: WO2006/123725, 2006, A1. Location in patent: Page/Page column 40

3-Cyanocinnamic acid(16642-93-6)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
• Ethyl cinnamate
• alpha-Methylcinnamic acid
• Propyl cinnamate
• Stearic acid
• Octyl 4-methoxycinnamate
• Cinnamic acid
• 3-(Trifluoromethyl)cinnamic acid
• trans-Cinnamic acid
• 4-Nitrocinnamic acid
• 3-Nitrocinnamic acid
• Methyl cinnamate
• Folic acid
• Citric acid
• 4-Methoxycinnamic acid
• Ascoric Acid
• 3-(3-CYANO-PHENYL)-ACRYLIC ACID METHYL ESTER
• 3-(3-CYANO-PHENYL)-2-METHYL-ACRYLIC ACID ETHYL ESTER