5-Bromo-2-hydroxynicotinic acid Chemical Properties

Melting point:

287°C

Boiling point:

354.7±42.0 °C(Predicted)

Density 

2.015±0.06 g/cm3(Predicted)

Flash point:

287°C

storage temp. 

Inert atmosphere,Room Temperature

pka

2.09±0.20(Predicted)

form 

powder to crystal

color 

Light orange to Yellow to Green

Decomposition 

287 ºC

InChI

InChI=1S/C6H4BrNO3/c7-3-1-4(6(10)11)5(9)8-2-3/h1-2H,(H,8,9)(H,10,11)

InChIKey

GYXOTADLHQJPIP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

104612-36-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

29333990

5-Bromo-2-hydroxynicotinic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal

Synthesis Reference(s)

Synthetic Communications, 19, p. 553, 1989 DOI: 10.1080/00397918908050699
Synthesis, p. 528, 2002 DOI: 10.1055/s-2002-20959

Synthesis

General procedure for the synthesis of 5-bromopyridine-3-carboxylic acid-2-one from 2-hydroxynicotinic acid: the compound was prepared according to the method of Y.S. Lo (Synthetic Communications, 1989, 553). Bromine (0.77 eq.) was slowly added dropwise to a stirred solution of 50% NaOH (2.4 eq.) in water (1 M solution) at 0 °C. After 5 min, 50% NaOH (3 eq.) was appended to the mixture, followed by the addition of solid 2-hydroxynicotinic acid (1 eq.) and the resultant solution was stirred continuously at 50 °C. After 20 h, a mixture of bromine ( 0.38 eq.) and a pre-prepared solution of 50% NaOH (1.2 eq.) in water (1 M solution) and continued stirring at 50 °C for 24 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and acidified to pH 2 with concentrated hydrochloric acid to precipitate the solid product. The solid was separated by filtration, washed sequentially with warm water/isopropanol (3:1) and ether, and dried to give 5-bromo-2-hydroxynicotinic acid in 87% yield as an off-white solid. The product characterization data were as follows: 1H NMR (400 MHz, DMSO) δ 8.25 (1H, d, J = 2.7 Hz), 8.33 (1H, d, J = 2.7 Hz), 13.84 (2H, bs); 13C NMR (400 MHz, DMSO) δ 99.45, 117.97, 142.01, 147.42, 163.22, 163.88; MS (ES-) m/z 218-216 (M-H)-.

References

[1] Patent: WO2004/110442, 2004, A1. Location in patent: Page 17; 18
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 9, p. 2566 - 2569
[3] Patent: US2002/161000, 2002, A1
[4] Patent: US2006/287292, 2006, A1. Location in patent: Page/Page column 26
[5] Organic Process Research and Development, 2008, vol. 12, # 4, p. 603 - 613

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