5-BROMO-2-METHOXY-NICOTINIC ACID Chemical Properties

Melting point:

156-158

Boiling point:

324.8±42.0 °C(Predicted)

Density 

1.713

storage temp. 

Inert atmosphere,Room Temperature

pka

2.97±0.10(Predicted)

form 

solid

Appearance

White to off-white Solid

InChI

InChI=1S/C7H6BrNO3/c1-12-6-5(7(10)11)2-4(8)3-9-6/h2-3H,1H3,(H,10,11)

InChIKey

SJLXURQPRRMPIV-UHFFFAOYSA-N

SMILES

C1(OC)=NC=C(Br)C=C1C(O)=O

CAS DataBase Reference

54916-66-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

nwg

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:ALFA

5-BROMO-2-METHOXY-NICOTINIC ACID Usage And Synthesis

Uses

5-Bromo-2-methoxy-nicotinic acid is used as an intermediate in pharmaceutical synthesis and can be employed to prepare RXFP1 receptor agonists. Its synthetic products can selectively activate the RXFP1 receptor for the treatment of heart failure, with an EC50 value of approximately 6.3nM.

Synthesis

General procedure for the synthesis of 5-bromo-2-methoxynicotinic acid from 2-methoxynicotinic acid: 2-methoxynicotinic acid (20 g, 130.60 mmol) was dissolved in H2O (1500 mL) at room temperature, followed by slow addition of Br2 (20 mL, 375.45 mmol). The reaction mixture was stirred continuously at room temperature overnight. Upon completion of the reaction, the solid product was collected by filtration and washed thoroughly with deionized water and finally dried to afford 5-bromo-2-methoxynicotinic acid (25 g, 82% yield). The structure of the product was confirmed by 1H-NMR (DMSO-d6, 400 MHz) and mass spectrometry (MS): 1H-NMR δ 13.33 (br s, 1H), 8.47 (d, J = 2.4 Hz, 1H), 8.21 (d, J = 2.4 Hz, 1H), 3.90 (s, 3H); MS (M + H)+ m/z: 232/234.

References

[1] Patent: WO2013/33971, 2013, A1. Location in patent: Page/Page column 144
[2] Patent: US2014/213571, 2014, A1. Location in patent: Paragraph 0572

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