2-Amino-3-fluorobenzoic acid Chemical Properties

Melting point:

171-172°C

Boiling point:

294.4±25.0 °C(Predicted)

Density 

1.430±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

4.60±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C7H6FNO2/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3H,9H2,(H,10,11)

InChIKey

KUHAYJJXXGBYBW-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=CC(F)=C1N

CAS DataBase Reference

825-22-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-24/25

HazardClass 

IRRITANT

HS Code 

29223990

2-Amino-3-fluorobenzoic acid Usage And Synthesis

Application

2-Amino-3-fluorobenzoic acid is a carboxylic acid derivative and can be used as a pharmaceutical intermediate.

Chemical Properties

white to light yellow crystal powder

Synthesis

7-Fluoro-1H-indole-2,3-dione (13.0 g, 78.7 mmol) was used as raw material, which was dissolved in 10N sodium hydroxide solution (125 mL), heated to 70°C and stirred for 1 hour. At the same temperature, 30% hydrogen peroxide solution (25 mL) was added slowly and dropwise over 20 minutes and the reaction continued to be stirred at 70 °C for 1 hour. Upon completion of the reaction, the reaction solution was cooled in an ice bath and concentrated. Subsequently, hydrochloric acid was slowly added to adjust the pH of the solution to 4. The organic phase was extracted with ethyl acetate, and the extract was washed with saturated brine and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to give the crude product. The crystals were collected by filtration to finally obtain 2-amino-3-fluorobenzoic acid (7.15 g, 59% yield). The NMR hydrogen spectrum (CDCl3) data were as follows: δ 6.00 (2H, broad single peak), 6.60 (1H, double-triple peak, J = 5.2 Hz, 8.0 Hz), 7.16 (1H, multiple peaks, J = 1.4 Hz, 8.0 Hz, 11.2 Hz), 7.72 (1H, triple-double peaks, J = 1.4 Hz, 8.0 Hz), and one additional hydrogen signal was masked.

References

[1] Organic Syntheses, 2002, vol. 79, p. 196 - 196
[2] Patent: US2003/187014, 2003, A1
[3] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1958, vol. 148, p. 481,488
[4] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 7, p. 2151 - 2163
[5] European Journal of Medicinal Chemistry, 1994, vol. 29, # 10, p. 743 - 751

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