5-Fluoro-2-nitropyridine Chemical Properties

Boiling point:

245.0±20.0 °C(Predicted)

Density 

1.439±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

-5.01±0.22(Predicted)

form 

solid

color 

Light yellow to yellow

InChI

InChI=1S/C5H3FN2O2/c6-4-1-2-5(7-3-4)8(9)10/h1-3H

InChIKey

CGFYNRVHPARGFY-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933399990

5-Fluoro-2-nitropyridine Usage And Synthesis

Uses

5-Fluoro-2-nitropyridine is mainly used as a pharmaceutical intermediate. It can be used to prepare substituted heterocyclic compounds with cell proliferation inhibitory activity.

Synthesis

General procedure for the synthesis of 5-fluoro-2-nitropyridine from 2-amino-5-fluoropyridine: 2-amino-5-fluoropyridine (6.0 g, 53.51 mmol, 1.0 eq.) was dissolved in concentrated H2SO4 (60 ml) and cooled to 0 °C (solution A). In another flask, hydrogen peroxide (13 ml) was slowly added to concentrated sulfuric acid at 0°C (Solution B). Solution A was added dropwise to solution B at 0°C. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was poured into ice-cold water and the product was extracted with EtOAc. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give pure 5-fluoro-2-nitropyridine (3.0 g, 39.45% yield). Mass spectrum (electrospray ionization): m/z 142.09 [M + H]+.

References

[1] Patent: US2004/209886, 2004, A1
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3627 - 3644
[3] Patent: WO2015/131080, 2015, A1. Location in patent: Paragraph 001083; 001084
[4] Patent: US2010/160340, 2010, A1. Location in patent: Page/Page column 7
[5] Patent: WO2012/97682, 2012, A1. Location in patent: Page/Page column 158

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