Benzoic acid, 2-amino-6-hydroxy- Chemical Properties

Melting point:

148℃

Boiling point:

352.2±32.0 °C(Predicted)

Density 

1.491

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

3.30±0.25(Predicted)

form 

Solid

color 

Light Brown to Brown

Safety Information

HS Code 

2922500090

Benzoic acid, 2-amino-6-hydroxy- Usage And Synthesis

Uses

6-Hydroxy-o-aminobenzoic acid is a carboxylic acid derivative that can be used as a pharmaceutical synthesis intermediate.

Synthesis

General procedure for the synthesis of 6-hydroxy-o-toluic acid from 2-amino-6-methoxybenzoic acid: boron tribromide (1 M in dichloromethane, 3 eq.) was slowly added dropwise to an anhydrous dichloromethane solution of 2-amino-6-methoxybenzoic acid (1 eq.) at -78 °C (dry ice/acetone bath). The reaction mixture was stirred at room temperature and under nitrogen protection for 18 hours. Upon completion of the reaction, the reaction was quenched by the addition of ethanol and methanol, followed by evaporation to remove the solvent to give a brown solid product. The product can be used in subsequent reactions without further purification. The product was a brown solid in 75% yield.

References

[1] European Journal of Medicinal Chemistry, 2014, vol. 76, p. 343 - 351
[2] Journal of Organic Chemistry, 1991, vol. 56, # 23, p. 6666 - 6671

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