3-AMINO-5-CHLOROBENZOIC ACID Chemical Properties

Boiling point:

383.3±27.0 °C(Predicted)

Density 

1.476±0.06 g/cm3(Predicted)

storage temp. 

Store at room temperature

pka

3.99±0.10(Predicted)

Appearance

Off-white to light brown Solid

CAS DataBase Reference

21961-30-8

3-AMINO-5-CHLOROBENZOIC ACID Usage And Synthesis

Chemical Properties

light yellow crystal powder

Hazard

Low toxicity by ingestion.

Synthesis

General procedure for the synthesis of 3-amino-5-chlorobenzoic acid from 3-chloro-5-nitrobenzoic acid: isopropanol (78 mL), ammonium chloride (0.18 g) and reduced iron powder (1.07 g) were added to a mixture of water (20 mL). After stirring the reaction mixture at 90 °C for 1 h, 3-chloro-5-nitrobenzoic acid (Compound 0004-1, 1.1 g) was slowly added and stirring was continued for 3 h at the same temperature. After completion of the reaction, the reaction solution was cooled to room temperature, washed with methanol and the filtrate was concentrated under reduced pressure to give the crude product. Finally, the crude product was purified by silica gel column chromatography (eluent: methanol-chloroform mixed solvent) to afford 3-amino-5-chlorobenzoic acid (Compound 0004-2, 368 mg) as a light brown solid.

References

[1] Patent: WO2003/101959, 2003, A1. Location in patent: Page 225-226
[2] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 73
[3] Justus Liebigs Annalen der Chemie, 1881, vol. 208, p. 312
[4] Journal of the American Chemical Society, 1954, vol. 76, p. 6336,6337
[5] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 16, p. 4557 - 4561

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