2-Fluoro-3-hydroxypyridine Chemical Properties

Melting point:

131-133°C

Boiling point:

306.7±22.0 °C(Predicted)

Density 

1.325±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO, Methanol

pka

4.92±0.10(Predicted)

form 

Solid

color 

Pale Yellow

CAS DataBase Reference

174669-74-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-37

HazardClass 

IRRITANT

HS Code 

29339900

2-Fluoro-3-hydroxypyridine Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

A pyridine derivative used in the preparation of imaging agents for nicotinic α4β2 receptor.

Uses

As a pyridine derivative, 2-Fluoro-3-hydroxypyridine can be used in the preparation of imaging agents for nicotinic α4β2 receptor.

Synthesis

100 mL of pyridine hydrofluoride (Py-(HF)x, 70% hydrogen fluoride and 30% pyridine, purchased from Fluka) was cooled at 0°C. 3.7 g of 2-amino-3-hydroxypyridine (molecular weight: 110.12, 33.6 mmol) and 3 g of NaNO2 (molecular weight: 69.00, 43.5 mmol) were added to it in sequence, handling with caution. The reaction mixture was stirred at 0 °C for 1 h, followed by slow alkalinization with 10 N NaOH aqueous solution. The mixture was transferred to a partition funnel and extracted with EtOAc. The organic phases were combined, washed sequentially with water and brine, dried over Na2SO4 and concentrated to dryness. The residue was purified by silica gel column chromatography (eluent: heptane/EtOAc, 50/50) to give 2.5 g (65% yield) of solid 2-fluoro-3-hydroxypyridine, which did not require further purification. Thin layer chromatography (TLC) Rf value (EtOAc/heptane, 80/20): 0.65. melting point: 131 °C. 1H NMR (DMSO-d6, 298 K): δ 10.41 (s, 1H), 7.64 (td, J=1.7 and 4.7 Hz, 1H), 7.42 (dd, J=1.7,1.7 and 10.8 Hz, 1H). 7.17 (ddd, J=1.3,4.7 and 7.8 Hz, 1H).13C NMR (DMSO-d6, 298K): δ 152.8 (d, J1F-C=233 Hz, C), 140.2 (d, J2F-C=27 Hz, C), 135.6 (d, J3F-C=13 Hz, CH), 126.2 (d, J3F -C=5 Hz, CH), 122.6 (CH). Mass spectrum (DCI/NH4+): C5H4FNO: 131 [M+NH4+], 114 [M+H+]. Elemental analysis (C5H4FNO) is consistent with theoretical values for C, H, and N.

References

[1] Patent: US2005/249662, 2005, A1. Location in patent: Page/Page column 8-9
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 1998, vol. 41, # 5, p. 451 - 463
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 2008, vol. 51, # 9, p. 336 - 342
[4] Patent: US2010/29650, 2010, A1. Location in patent: Page/Page column 64
[5] Organic and Biomolecular Chemistry, 2015, vol. 13, # 12, p. 3667 - 3676

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