2-AMINO-3-BROMOBENZOIC ACID Chemical Properties

Melting point:

173 °C

Boiling point:

343.5±32.0 °C(Predicted)

Density 

1.793±0.06 g/cm3(Predicted)

Flash point:

161°C

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

pka

4.55±0.10(Predicted)

form 

Solid

color 

White to pale yellow

λmax

323nm(Phosphate buffer sol.)(lit.)

InChI

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

InChIKey

SRIZNTFPBWRGPB-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

20776-51-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn,T

Risk Statements 

22-36/37/38-25

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2922498590

2-AMINO-3-BROMOBENZOIC ACID Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

2-amino-3-bromobenzoic acid is used as pharmaceutical intermediates.

Synthesis

The general procedure for the synthesis of 2-amino-3-bromobenzoic acid from 7-bromoindigo is as follows: commercially available 7-bromoindigo (18.0 g, 79.6 mmol) was dissolved in 5% aqueous sodium hydroxide solution (400 mL), and 30% aqueous hydrogen peroxide solution (22.5 mL, 199 mmol) was added slowly and dropwise at 50 °C. The reaction mixture was stirred continuously at 50 °C for 30 min. Subsequently, the reaction solution was cooled to room temperature and neutralized to neutral with 2.0 mol/L hydrochloric acid solution. The precipitated solid product was collected by filtration and dried under reduced pressure overnight to give the final target compound 2-amino-3-bromobenzoic acid.

References

[1] Patent: EP2708540, 2014, A1. Location in patent: Paragraph 0085
[2] Patent: US2008/153802, 2008, A1. Location in patent: Page/Page column 114
[3] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1958, vol. 148, p. 481,488
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 4, p. 1270 - 1274
[5] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 9, p. 831 - 834

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