2-Amino-6-bromobenzoic acid Chemical Properties

Melting point:

136 °C

Boiling point:

348.9±32.0 °C(Predicted)

Density 

1.793±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder

pka

0.85±0.10(Predicted)

color 

Light brown to beige

Sensitive 

Light Sensitive

InChI

InChI=1S/C7H6BrNO2/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3H,9H2,(H,10,11)

InChIKey

BNQPROAXWQCNKO-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2916399090

2-Amino-6-bromobenzoic acid Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-amino-6-bromobenzoic acid from 4-bromoindoline-2,3-dione: Commercially available 4-bromoindigo (2.50 g, 11.1 mmol) was dissolved in 1.5 mol/L aqueous sodium hydroxide solution (20 mL), and 33% aqueous hydrogen peroxide solution (1 mL) was added slowly and dropwise at 55 °C. The reaction mixture was stirred continuously at 55 °C for 30 min and then cooled to room temperature. Subsequently, the reaction solution was neutralized with 2.0 mol/L hydrochloric acid solution and finally purified by HP-20 resin column to obtain the target product 2-amino-6-bromobenzoic acid (1.60 g, 67% yield).

References

[1] Patent: EP2708540, 2014, A1. Location in patent: Paragraph 0092
[2] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1958, vol. 148, p. 481,488
[3] Patent: WO2011/28741, 2011, A1. Location in patent: Page/Page column 202
[4] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 9, p. 831 - 834

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