3-AMINO-5-BROMOBENZOIC ACID Chemical Properties

Melting point:

217-221 °C

Boiling point:

398.3±32.0 °C(Predicted)

Density 

1.793

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

solid

pka

3.97±0.10(Predicted)

Appearance

White to off-white Solid

InChI

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

InChIKey

RQSXRGSPGHZKFT-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2922498590

3-AMINO-5-BROMOBENZOIC ACID Usage And Synthesis

Uses

peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for the synthesis of 3-amino-5-bromobenzoic acid from 3-bromo-5-nitrobenzoic acid was as follows: concentrated hydrochloric acid (30 mL) was slowly added to a solution containing 3-bromo-5-nitrobenzoic acid (7.02 g, 28.54 mmol) and ethanol (150 mL), and the mixture was stirred for 5 min at room temperature. Subsequently, tin (II) chloride was added and the reaction mixture was stirred at 50 °C for 2 hours. After completion of the reaction, the mixture was cooled to room temperature. The pH was adjusted to 9 with 8 M sodium hydroxide solution, at which point a solid precipitated. The solids were removed by filtration. The filtrate was acidified to pH 5 with hydrochloric acid and the target product 3-amino-5-bromobenzoic acid was precipitated, which was filtered to give 5.8 g (94% yield). The product was analyzed by HPLC/MS with a retention time of 4.67 min, LRMS: m/z 216 (M-1).

References

[1] Patent: EP2196465, 2010, A1. Location in patent: Page/Page column 42; 43
[2] Patent: EP2394998, 2011, A1. Location in patent: Page/Page column 22-23
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 23, p. 10479 - 10497
[4] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 169
[5] Organic and Biomolecular Chemistry, 2005, vol. 3, # 20, p. 3757 - 3766

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