5-Bromo-2-pyridinecarboxylic Acid Chemical Properties

Melting point:

173-175°C

Boiling point:

319.5±27.0 °C(Predicted)

Density 

1.813±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in methanol.

form 

Powder

pka

3.41±0.10(Predicted)

color 

White to off-white

InChI

InChI=1S/C6H4BrNO2/c7-4-1-2-5(6(9)10)8-3-4/h1-3H,(H,9,10)

InChIKey

MNNQIBXLAHVDDL-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

30766-11-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26-37/39

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

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5-Bromo-2-pyridinecarboxylic Acid Usage And Synthesis

Uses

5-Bromopyridine-2-carboxylic acid is used as a pharmaceutical intermediate. Store in cool, dry place in a well sealed container. Store away from oxidizing agents.

Chemical Properties

white Cryst

Uses

5-Bromopyridine-2-carboxylic acid is used as a pharmaceutical intermediate.

Synthesis

4.1.7 Synthesis of 5-bromopyridine-2-carboxylic acid (11): In a 250 mL three-necked flask assembled with a stirrer, thermometer, and condenser tube, add 150 mL of water and 5-bromo-2-methylpyridine (10) (6.0 g, 35 mmol). After turning on the stirring and heating to 80 °C, potassium permanganate (KMnO4) (24.8 g, 157 mmol) was added in three batches at 1 h intervals. The reaction temperature was maintained at 80 °C and stirring was continued for 3-4 hours. Upon completion of the reaction, filtration was carried out to obtain a clarified filtrate. The pH of the filtrate was adjusted to 4-5 with concentrated hydrochloric acid, at which point a white solid precipitated. The filtrate was filtered to collect a small amount of product (11). The filtrate was concentrated under vacuum and an appropriate amount of ethanol was added to the residue to dissolve compound (11), at which time a large amount of white solid precipitated, the filtrate was again withdrawn and the solid discarded. Finally, the filtrate was concentrated under vacuum to give a light yellow solid product (11) (3.0 g, 39% yield).

References

[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3228 - 3236
[2] Journal fuer Praktische Chemie (Leipzig), 1932, vol. <2> 133, p. 36,49
[3] Heterocycles, 1981, vol. 15, # 1, p. 213 - 223
[4] Synthesis, 2003, # 4, p. 551 - 554
[5] Patent: US2005/113374, 2005, A1. Location in patent: Page/Page column 8

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