2-Fluoroisonicotinic acid Chemical Properties

Melting point:

200 °C (dec.)(lit.)

Boiling point:

396.6±22.0 °C(Predicted)

Density 

1.419±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

3.03±0.10(Predicted)

form 

Powder

color 

White to Almost white

InChI

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

InChIKey

JMPFWDWYGOWUFP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

402-65-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Fluoroisonicotinic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder, solubility in water, ethanol, and methanol, as well as high solubility in organic solvents. 

Uses

2-Fluoroisonicotinic acid is a catalyst in organic reactions and serves as a starting material for the synthesis of fluorinated compounds. Furthermore, it plays a role in the synthesis of dyes, pigments, and various other organic compounds.

Synthesis

General procedure for the preparation of 2-fluoroisonicotinic acid: 1. 5.00 g (45 mmol) of 2-fluoro-4-methylpyridine and 1.00 g (17 mmol) of KOH were added to a reaction flask followed by 50 ml of pyridine as solvent. 2. The reaction mixture was heated to reflux. 3. 20.00 g (127 mmol) of potassium permanganate was added in batches over 30 minutes at reflux temperature. 4. After addition, the reaction mixture was continued to be heated at reflux for 1.5 hours. 5. Upon completion of the reaction, the mixture was cooled to room temperature in an ice bath. 6. 100 ml of water was added to the cooled mixture and the pH was subsequently adjusted to 1 with concentrated hydrochloric acid. 7. 100 ml of ethyl acetate was added and the insoluble material was removed by filtration. 8. The aqueous phase was extracted twice with ethyl acetate, 100 ml each time. 9. Combine all ethyl acetate phases and dry with magnesium sulfate. 10. The dried organic phase was concentrated under pressure to give 2.70 g of 2-fluoroisonicotinic acid. Yield: 42%.

References

[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 2745 - 2766
[2] Patent: US6358978, 2002, B1
[3] Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1667 - 1675
[4] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[5] Journal of the American Chemical Society, 1949, vol. 71, p. 4152

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