TRANS-2,4-DICHLOROCINNAMIC ACID Chemical Properties

Melting point:

233-235 °C(lit.)

Boiling point:

359.4±27.0 °C(Predicted)

Density 

1.3944 (estimate)

storage temp. 

Sealed in dry,Room Temperature

pka

4.17±0.13(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

1201-99-6(CAS DataBase Reference)

EPA Substance Registry System

2-Propenoic acid, 3-(2,4-dichlorophenyl)- (1201-99-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38

Safety Statements 

37/39-26

WGK Germany 

3

Hazardous Substances Data

1201-99-6(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

TRANS-2,4-DICHLOROCINNAMIC ACID Usage And Synthesis

Synthesis

To a 5 mL round-bottomed flask equipped with a stirrer, trans-2'-hydroxychalcone (1a, 1 mmol), potassium carbonate (K2CO3, 1.38 g, 10 mmol), 35% hydrogen peroxide solution (H2O2, 0.5 mL) and acetonitrile (2 mL) were added. The reaction mixture was stirred at room temperature and the progress of the reaction was monitored by thin layer chromatography (TLC) until the complete disappearance of the ingredients. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. A 1 mol/L hydrochloric acid solution was added to the residue and the resulting solid was collected by filtration to afford the target product 2,4-dichlorostyrene acid (2a) as a white solid (133 mg, 90% yield). The structure of the product was confirmed by NMR hydrogen (1H NMR, 300 MHz, DMSO-d6) and NMR carbon (13C NMR, 300 MHz, DMSO-d6) spectra: 1H NMR (DMSO-d6) δ 7.58 (d, 1H, J = 16 Hz), 7.42-7.69 (m, 5H), 6.53 (d, 1H, J = 16 Hz); 13C NMR (DMSO-d6) δ 167.7, 144.0, 134.3, 130.3, 128.9, 128.2, 119.3.

References

[1] Journal of the Brazilian Chemical Society, 2013, vol. 24, # 3, p. 518 - 522

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