3-AMINO-2-BROMO-BENZOIC ACID METHYL ESTER Chemical Properties

Boiling point:

314.1±22.0 °C(Predicted)

Density 

1.583 g/mL at 25 °C

refractive index 

n20/D1.601

Flash point:

>110℃

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

1.39±0.10(Predicted)

form 

liquid

color 

Clear, bright orange/amber

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

RIDADR 

2810

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2922498590

3-AMINO-2-BROMO-BENZOIC ACID METHYL ESTER Usage And Synthesis

Uses

Methyl 3-Amino-2-bromobenzoate is used in preparation of Carbazole-based compounds and its application as IDO inhibitor.

Synthesis

Methyl 2-bromo-3-nitrobenzoate (12.9 g, 49.5 mmol) was used as feedstock and prepared according to the method described by Webber ES et al. (Patent Application No. WO 01/16136 A2). The feedstock was refluxed with SnCl2 (42 g, 223 mmol) in a mixed solution of methanol (225 mL, 0.2 M) and H2O (5.3 g, 243 mmol) for 2 hours. After completion of the reaction, it was cooled to room temperature and diatomaceous earth (20 g) and dichloromethane (1 L) were added, followed by the slow addition of 3 N aqueous sodium hydroxide solution (150 mL) under vigorous stirring. The reaction mixture was filtered and the organic phase was washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove all volatiles to afford the intermediate methyl 3-amino-2-bromobenzoate (11.4 g) in 98% yield.1H-NMR (d6-DMSO) δ: 7.12 (dd, 1H, J = 8.1, 7.5 Hz), 6.93 (dd, 1H, J = 8.1, 1.6 Hz), 6.80 ( dd, 1H, J = 7.4, 1.6 Hz), 5.57 (s, 2H), 3.81 (s, 3H).

References

[1] Patent: WO2004/63198, 2004, A1. Location in patent: Page 77
[2] Tetrahedron, 2010, vol. 66, # 29, p. 5402 - 5406
[3] Tetrahedron, 2000, vol. 56, # 2, p. 165 - 173
[4] Journal of Organic Chemistry, 1988, vol. 53, # 6, p. 1170 - 1176
[5] Patent: EP950657, 1999, A2

3-AMINO-2-BROMO-BENZOIC ACID METHYL ESTER(106896-48-4)Related Product Information

• METHYL 2-BROMO-3-NITROBENZOATE
• Ethyl 2-bromo-3-nitrobenzoate
• 3-AMINO-2-BROMO-BENZOIC ACID
• 3-AMINO-2-BROMO-BENZOIC ACID METHYL ESTER
• Benzoic acid, 4-fluoro-5-hydroxy-2-methoxy-, methyl ester
• METHYL 4-CHLORO-3,5-DINITROBENZOATE
• METHYL 4-BROMO-2-METHOXYBENZOATE 98