5-Fluoro-2-picolinic acid Chemical Properties

Melting point:

164-166℃

Boiling point:

275.1±20.0 °C(Predicted)

Density 

1.419±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.58±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C6H4FNO2/c7-4-1-2-5(6(9)10)8-3-4/h1-3H,(H,9,10)

InChIKey

JTKFIIQGMVKDNZ-UHFFFAOYSA-N

SMILES

C1(C(O)=O)=NC=C(F)C=C1

CAS DataBase Reference

107504-08-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933399990

5-Fluoro-2-picolinic acid Usage And Synthesis

Uses

5-Fluoro-2-pyridinecarboxylic acid, a common organic synthetic intermediate, is mainly used for the structural modification and derivatization of pyridine-containing drug molecules and bioactive molecules. The carboxyl group on the pyridine ring can be converted to an ester group, but acid-promoted esterification is generally not used. A more common approach is to first convert the carboxyl group to an acyl chloride using sulfoxide, followed by the addition of an alcohol to convert it to an ester group. Furthermore, the carboxyl group on this compound can also be converted to a trifluoromethyl group. Finally, the nitrogen atom on the pyridine ring can also be oxidized to nitrogen oxides.

Synthesis

Potassium phosphate monobasic (1.4 g, 10 mmol) in water (10 mL) was added to a solution of 5-fluoropyridine-2-carbaldehyde (0.50 g, 4.0 mmol, Frontier) in DMSO (10 mL). Sodium chlorite (0.9 g, 0.008 mol) in water (10 mL) was added, and the reaction continued for 1 hour. The mixture was saturated with NaCl, then diluted with EtOAc. The organic layer was further washed with brine, dried over sodium sulfate and concentrated to afford 5-FLUORO-2-PICOLINIC ACID (370 mg, 65%).

References

[1] Patent: WO2011/28685, 2011, A1. Location in patent: Page/Page column 85; 86

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