2-Fluoronicotinamide Chemical Properties

Melting point:

120.9-122 °C

Boiling point:

287.9±25.0 °C(Predicted)

Density 

1.327±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

14.10±0.50(Predicted)

form 

crystalline powder

color 

White to off white

Safety Information

HS Code 

2933399990

2-Fluoronicotinamide Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-fluoronicotinamide from 2-fluoronicotinic acid: thionyl chloride (40 mL) was added to 2-fluoronicotinic acid (2.0 g, 14.3 mmol) and the reaction mixture was refluxed for 18 hours. Upon completion of the reaction, it was cooled to room temperature and concentrated under reduced pressure. Benzene (100 mL) was added to the residue, followed by passing ammonia into the suspension for 3 hours. The reaction flask was sealed and stirring was continued for 18 hours, after which it was concentrated under reduced pressure. Water was added to the residue and extracted with ethyl acetate (EtOAc). The organic phase was washed sequentially with water and brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give 2-fluoronicotinamide (0.6 g, 30% yield). Mass spectrum (electrospray ionization, ES) showed m/z 141.1 ([M + H]+). 1H NMR (400 MHz, CDCl3) δ 8.32 (d, 1H, J = 4.5 Hz), 8.17 (m, 1H), 7.92 (br s, 1H), 7.79 (br s, 1H), 7.44 (m, 1H).

References

[1] Patent: WO2005/66126, 2005, A1. Location in patent: Page/Page column 61
[2] Journal of the Chemical Society, 1951, p. 3512
[3] Journal of the American Chemical Society, 1949, vol. 71, p. 1125

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