ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Hydroxypyridine 2-Fluoro-5-hydroxypyridine

2-Fluoro-5-hydroxypyridine

Product Name2-Fluoro-5-hydroxypyridine
CAS55758-32-2
MFC5H4FNO
MW113.09
EINECS
MOL File55758-32-2.mol

Chemical Properties

Melting point	148-150°C
Boiling point	319.8±22.0 °C(Predicted)
Density	1.325±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	soluble in Methanol
form	powder to crystal
pka	9.03±0.10(Predicted)
color	White to Almost white
CAS DataBase Reference	55758-32-2(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi,Xn
Risk Statements	36/37/38-41-37/38-22
Safety Statements	26-36/37/39-39-37
Hazard Note	Irritant
HS Code	29339900

Usage And Synthesis

Chemical Properties

White fine crystalline powder

Uses

2-Fluoro-5-hydroxypyridine serves as a precursor for synthesizing 2-fluoro-5-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridine and 5-(2,6-dichlorobenzyloxy)-2-fluoropyridine[3][4].

Synthesis

3-Pyridinol,6-fluoro-,acetate(ester)(9CI)

209328-51-8

55758-32-2

5-Acetoxy-2-fluoropyridine (2.26 g, 14.6 mmol, from Step 8d) was used as raw material and dissolved in 20% aqueous NaOH (15 mL). The reaction mixture was stirred at room temperature for 1 hour. Subsequently, the reaction solution was neutralized with concentrated HCl. The aqueous phase was extracted with ethyl acetate. The organic phases were combined, dried with anhydrous MgSO4 and concentrated under reduced pressure to remove the solvent. Purification by silica gel column chromatography (eluent: CHCl3/MeOH, 98:2) afforded 1.31 g of the target product 2-fluoro-5-hydroxypyridine in 79% yield. Mass spectra (MS) m/z: 114 (M + H)+, 131 (M + NH4)+; 1H NMR (CDCl3, 300 MHz) δ 6.84 (dd, J = 1.85,5.14 Hz, 1H), 7.43 (m, 1H), 7.81 (t, J = 2.84 Hz, 1H).

References

[1] Patent: US6001849, 1999, A
[2] Patent: US6133253, 2000, A
[3]Gardinier, K. M., Gernert, D. L., Porter, W. J., Reel, J. K., Ornstein, P. L., Spinazze, P., Stevens, F. C., Hahn, P., Hollinshead, S. P., Mayhugh, D., Schkeryantz, J., Khilevich, A., Frutos, O. D., Gleason, S. D., Kato, A. S., Luffer-Atlas, D., Desai, P. V., Swanson, S., Burris, K. D., … Witkin, J. M. (2016). Discovery of the First α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptor Antagonist Dependent upon Transmembrane AMPA Receptor Regulatory Protein (TARP) γ-8. Journal of Medicinal Chemistry, 59(10), 4753–4768. https://doi.org/10.1021/acs.jmedchem.6b00125
[4]Gill, A. L., Frederickson, M., Cleasby, A., Woodhead, S. J., Carr, M. G., Woodhead, A. J., Walker, M. T., Congreve, M. S., Devine, L. A., Tisi, D., O'Reilly, M., Seavers, L. C. A., Davis, D. J., Curry, J., Anthony, R., Padova, A., Murray, C. W., Carr, R. A. E., & Jhoti, H. (2004). Identification of Novel p38α MAP Kinase Inhibitors Using Fragment-Based Lead Generation. Journal of Medicinal Chemistry, 48(2), 414–426. https://doi.org/10.1021/jm049575n

2-Fluoro-5-hydroxypyridine

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