5-FLUORO-2-HYDROXY-3-NITROPYRIDINE Chemical Properties

Boiling point:

249.1±40.0 °C(Predicted)

Density 

1.55±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

Solid

pka

6.43±0.10(Predicted)

Appearance

Light yellow to yellow Solid

Water Solubility 

Slightly soluble in water.

CAS DataBase Reference

136888-20-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

26-36/37

HS Code 

2933399990

5-FLUORO-2-HYDROXY-3-NITROPYRIDINE Usage And Synthesis

Chemical Properties

Yellow to light yellow liquid

Uses

It is used as a pharmaceutical intermediate.

Synthesis

a) Mix 2-hydroxy-5-fluoropyridine (1.20 g, 10.6 mmol) with concentrated sulfuric acid (2.7 mL), cool in an ice bath and stir. A mixture consisting of concentrated sulfuric acid (1 mL) and fuming nitric acid (1 mL) was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was gradually warmed to room temperature and subsequently heated to 85°C for 2 hours. Upon completion of the reaction, the mixture was cooled and poured into ice water. The precipitate was collected by filtration and dried to give 2-hydroxy-3-nitro-5-fluoropyridine (0.72 g, 43% yield) as a yellow solid.LRMS (m/z): 157 (M-1)+.1H NMR (300 MHz, DMSO-d6) δ: 8.28 (s, 1H), 8.67 (s, 1H).

References

[1] Patent: EP2527344, 2012, A1. Location in patent: Page/Page column 22
[2] Patent: WO2012/160030, 2012, A1. Location in patent: Page/Page column 66
[3] Patent: WO2006/114706, 2006, A1. Location in patent: Page/Page column 45
[4] Journal of Heterocyclic Chemistry, 1996, vol. 33, # 2, p. 287 - 293
[5] Patent: US2004/110785, 2004, A1. Location in patent: Page 211

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