5-PHENYL-2-FUROIC ACID Chemical Properties

Melting point:

150-154 °C (lit.)

Boiling point:

368.2±30.0 °C(Predicted)

Density 

1.254±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

powder to crystal

pka

3.15±0.10(Predicted)

color 

White to Light yellow

InChIKey

GUOMINFEASCICM-UHFFFAOYSA-N

CAS DataBase Reference

52938-97-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2932190090

MSDS

• Language:English Provider:SigmaAldrich

5-PHENYL-2-FUROIC ACID Usage And Synthesis

Synthesis

GENERAL METHODS: To a mixed solution of 5-(3-chlorophenyl)-2-furaldehyde (19a) (206 mg, 1.00 mmol) dissolved in tert-butanol (37.5 mL) and water (7.5 mL) was added sequentially NaH2PO4 (213 mg, 1.50 mmol), 2-methyl-2-butene (0.78 mL, 7.50 mmol) and NaClO2 (228 mg, 2.50 mmol). The reaction mixture was stirred at room temperature for 11 hours. After completion of the reaction, the volatile solvent was removed by distillation under reduced pressure and water and 1N hydrochloric acid were added. The mixture was extracted with ethyl acetate (EtOAc). The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure to give 5-phenyl-2-furoic acid (22a) (214 mg, 97% yield) as a white solid.

References

[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 21, p. 6384 - 6393,10
[2] Journal of Pharmaceutical Sciences, 1980, vol. 69, # 1, p. 107 - 110
[3] Patent: US2010/130556, 2010, A1. Location in patent: Page/Page column 25
[4] Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 491,494
[5] Heterocycles, 2014, vol. 89, # 2, p. 453 - 464

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