2-Fluoro-4-hydroxybenzoic acid Chemical Properties

Melting point:

199-202

Boiling point:

334.6±27.0 °C(Predicted)

Density 

1.492±0.06 g/cm3(Predicted)

storage temp. 

RT, stored under nitrogen

solubility 

soluble in Methanol

form 

powder to crystal

pka

3?+-.0.10(Predicted)

color 

White to Almost white

CAS DataBase Reference

65145-13-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36

HazardClass 

IRRITANT

HS Code 

2918290090

2-Fluoro-4-hydroxybenzoic acid Usage And Synthesis

Chemical Properties

Pale yellow liquid

Uses

2-Fluoro-4-hydroxybenzoic Acid, is a fluorinated building block used for the synthesis of more complex pharmaceutical and biologically active compounds. It is also fluorine substituted 4-hydroxybenzoates, which has been shown to have antioxidant activity.

Synthesis

General procedure for the synthesis of 2-fluoro-4-hydroxybenzoic acid from 2-fluoro-4-hydroxybenzonitrile: To a stirred solution of 2-fluoro-4-hydroxybenzonitrile (20.00 g, 145.9 mmol) in 160 mL of water was slowly added an aqueous 50% sodium hydroxide solution (40.00 g, 500.0 mmol). The reaction mixture was heated to reflux for 4 hours and subsequently cooled to room temperature. The cooled mixture was slowly poured into ice-cold concentrated hydrochloric acid and extracted with ether. The aqueous phase was adjusted to alkaline with saturated aqueous sodium bicarbonate, extracted again with ether and the ether layer was discarded. The aqueous phase was acidified with concentrated hydrochloric acid to pH < 2 and then extracted with ether. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 2-fluoro-4-hydroxybenzoic acid as a white solid (22.90 g, 100% yield). The product was characterized by 1H NMR (300 MHz, CD3COCD3) and 19F-NMR (300 MHz, CD3COCD3) with the following data: 1H NMR δ (ppm): 9.80 (b, 1H), 7.87 (t, 1H), 6.77 (dd, 1H), 6.66 (dd, 1H); 19F-NMR δ (ppm): -108.13 (s, decoupled).

References

[1] Patent: US2006/20146, 2006, A1. Location in patent: Page/Page column 30
[2] Molecular Crystals and Liquid Crystals (1969-1991), 1981, vol. 67, p. 1 - 24
[3] Patent: US6369261, 2002, B1. Location in patent: Page column 25

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