5-BROMO-6-HYDROXYNICOTINIC ACID Chemical Properties

Melting point:

>300

Boiling point:

348.1±42.0 °C(Predicted)

Density 

2.015±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

3.38±0.50(Predicted)

form 

powder to crystal

color 

White to Almost white

InChI

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

InChIKey

PQDLYKZCJBGXPQ-UHFFFAOYSA-N

SMILES

C1NC(=O)C(Br)=CC=1C(O)=O

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

29333990

5-BROMO-6-HYDROXYNICOTINIC ACID Usage And Synthesis

Chemical Properties

Light green solid

Synthesis

Synthesis of 5-bromo-6-hydroxynicotinic acid: 6-hydroxynicotinic acid (8 g, 57.6 mmol) was suspended in water (30 mL) and bromine (4.2 mL, 81.4 mmol) was slowly added under ice bath cooling conditions. After addition, the reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, the solid product was collected by filtration, washed with water and dried in a vacuum oven at 40 °C for 24 h to afford 5-bromo-6-hydroxynicotinic acid (12.1 g, 97% yield) as a tan solid. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 8.04 (d, J = 2.53 Hz, 1H), 8.16 (d, J = 2.27 Hz, 1H), 12.59 (br s, 1H), 12.90 (br s, 1H).

References

[1] Journal of Medicinal Chemistry, 2013, vol. 56, # 24, p. 9874 - 9896
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 15, p. 4892 - 4909
[3] Patent: WO2007/70818, 2007, A1. Location in patent: Page/Page column 103
[4] Patent: WO2006/88919, 2006, A2. Location in patent: Page/Page column 134-135
[5] Patent: US2008/85906, 2008, A1. Location in patent: Page/Page column 15

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