3,4-DIFLUORO-2-HYDROXYBENZOIC ACID Chemical Properties

Melting point:

177-179°C

Boiling point:

282℃

Density 

1.600

Flash point:

124℃

storage temp. 

Sealed in dry,Room Temperature

pka

2.32±0.13(Predicted)

Appearance

Off-white to light yellow Solid

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25

Safety Statements 

45

Hazard Note 

Harmful/Irritant

HS Code 

2918290090

3,4-DIFLUORO-2-HYDROXYBENZOIC ACID Usage And Synthesis

Synthesis

The general procedure for the synthesis of 3,4-difluoro-2-hydroxybenzoic acid from 2,3,4-trifluorobenzoic acid was carried out as follows: solid sodium hydroxide (4.52 g, 113 mmol) was added batchwise to a solution of dimethylimidazolidinone (10 mL) of 2,3,4-trifluorobenzoic acid (5.0 g, 28 mmol) under the conditions of cooling in an ice bath and stirring. Subsequently, the reaction mixture was heated to 120 °C and maintained at this temperature for 2 h. During this time, the progress of the reaction was monitored by TLC to confirm the complete consumption of 2,3,4-trifluorobenzoic acid. Upon completion of the reaction, the mixture was cooled to room temperature and acidified to pH 5-6 with 2N hydrochloric acid (7.5 mL).The precipitated white solid was collected by filtration, washed with excess water, and dried to afford the target product, 3,4-difluoro-2-hydroxybenzoic acid (3.6 g, 73.4% yield), with a melting point of 174-177 °C. The product structure was determined by 1H-NMR. The structure of the product was confirmed by 1H-NMR (400 MHz, DMSO-d6) and IR (KBr) spectroscopy: 1H-NMR δ 6.94-7.01 (m, 1H, aryl), 7.64-7.68 (m, 1H, aryl); IR 3208.9 cm-1 (OH), 1654.1 cm-1 (C=O), 1625.7 cm-1 (C =C, aromatic), 1315.2 cm-1 (C-O).

References

[1] Journal of Fluorine Chemistry, 2003, vol. 121, # 1, p. 97 - 99
[2] Medicinal Chemistry Research, 2015, vol. 24, # 9, p. 3516 - 3528
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2455 - 2458

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