2-FLUORO-5-HYDROXYBENZOIC ACID Chemical Properties

Melting point:

201-203°C

Boiling point:

354.8±27.0 °C(Predicted)

Density 

1.492±0.06 g/cm3(Predicted)

storage temp. 

RT, stored under nitrogen

pka

3.15±0.10(Predicted)

form 

Powder

Appearance

White to off-white Solid

CAS DataBase Reference

51446-30-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xi,Xn

Risk Statements 

36/37/38-51-41-22

Safety Statements 

26-36-39

Hazard Note 

Corrosive

HazardClass 

IRRITANT

HS Code 

2918290090

2-FLUORO-5-HYDROXYBENZOIC ACID Usage And Synthesis

Chemical Properties

off-white crytalline

Synthesis

Step 1: Methyl 2-fluoro-5-hydroxybenzoate (30.0 g, 176.47 mmol, 1.0 eq.) was dissolved in a solvent mixture of THF and H2O (3:1 v/v, total 350 mL). To this solution was added LiOH-H2O (22.2 g, 529.41 mmol, 3.0 eq.) at room temperature. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, THF was removed by distillation under reduced pressure and the residue was diluted with cold water. The pH was adjusted to about 3 with 1.5 N HCl aqueous solution and the aqueous phase was extracted with EtOAc (3 x 250 mL). The organic phases were combined, washed with brine (150 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give 2-fluoro-5-hydroxybenzoic acid as an off-white solid (25.1 g, 91% yield).MS m/z: [M-1]? = 155.4.

References

[1] Patent: WO2015/51043, 2015, A1. Location in patent: Paragraph 00248
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 17, p. 7818 - 7839

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