5-Nitropyridine-2-carboxylic acid Chemical Properties

Melting point:

218-220°C

Boiling point:

389.8±27.0 °C(Predicted)

Density 

1.570±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Soluble in dimethyl sulfoxide.

form 

Solid

pka

2.71±0.13(Predicted)

color 

Light Yellow

InChI

InChI=1S/C6H4N2O4/c9-6(10)5-2-1-4(3-7-5)8(11)12/h1-3H,(H,9,10)

InChIKey

QKYRCTVBMNXTBT-UHFFFAOYSA-N

SMILES

C1(C(O)=O)=NC=C([N+]([O-])=O)C=C1

CAS DataBase Reference

30651-24-2(CAS DataBase Reference)

NIST Chemistry Reference

Picolinic acid, 5-nitro-(30651-24-2)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-20/21/22

Safety Statements 

24/25-36/37

HS Code 

29333990

5-Nitropyridine-2-carboxylic acid Usage And Synthesis

Chemical Properties

Light Yellow Solid

Uses

It plays an important role in synthetic intermediate.

Uses

5-Nitropyridine-2-carboxylic acid is a useful synthetic intermediate.

Synthesis

General procedure for the synthesis of 5-nitro-2-pyridinecarboxylic acid from 2-bromo-5-nitropyridine: this method is based on the procedure reported by Oehlke, J.; Schroetter, E.; Dove, S.; Schick, H.; Niedrich, H. in Pharmazie 1983,38,591-596, with slight modifications. When N,N-dimethylformamide (DMF) was used instead of dimethylsulfoxide (DMSO) as solvent for the reaction with 2-bromo-5-nitropyridine and copper(I) cyanide, a subsequent hydrolysis step afforded the target product 5-nitro-2-pyridinecarboxylic acid in 70% yield. This product is usually used directly in subsequent reactions without further purification.

References

[1] Patent: WO2004/14904, 2004, A1. Location in patent: Page 53
[2] Pharmazie, 1983, vol. 38, # 9, p. 591 - 596
[3] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1951, vol. 288, p. 237,241
[4] Patent: WO2009/141386, 2009, A1. Location in patent: Page/Page column 89

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