2,6-dichloropyridin-3-ol Chemical Properties

Boiling point:

353.4±37.0 °C(Predicted)

Density 

1.561±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

3.86±0.10(Predicted)

Appearance

White to light brown Solid

InChI

InChI=1S/C5H3Cl2NO/c6-4-2-1-3(9)5(7)8-4/h1-2,9H

InChIKey

CDDCESLWCVAQMG-UHFFFAOYSA-N

SMILES

C1(Cl)=NC(Cl)=CC=C1O

2,6-dichloropyridin-3-ol Usage And Synthesis

Uses

2,6-Dichloro-3-hydroxypyridine is a pharmaceutical intermediate, and there are literature reports that it can be used to prepare drugs against HCV infection.

Synthesis

Preparation of Compound 1 Step 1 - A solution of 2,6-dichloropyridin-3-ylboronic acid (3 g, 15.71 mmol) in 30 mL of CH2Cl2 was slowly added to H2O2 (1.60 g, 47.12 mmol) at 0°C. The reaction mixture was stirred at room temperature for about 15 hours and then quenched with saturated aqueous NaHCO3 solution. Subsequently, 50 mL of Na2S2O3 aqueous solution was added and the pH was adjusted to <7 with 1 N HCl. The mixture was extracted with EtOAc (40 mL x 3), the organic layers were combined and washed with 100 mL of brine, dried over Na2SO4, filtered and the solvent was evaporated to give 2,6-dichloropyridin-3-ol (2.34 g, yield: 91.4%). The product was confirmed by 1H-NMR (CDCl3, 400MHz): δ 7.30 (d, J = 8.4Hz, 1H), 7.19 (d, J = 8.4Hz, 1H), 5.70 (br, 1H).

References

[1] Tetrahedron, 2005, vol. 61, # 6, p. 1417 - 1421
[2] Patent: WO2013/33900, 2013, A1. Location in patent: Page/Page column 27
[3] Patent: WO2013/33971, 2013, A1. Location in patent: Page/Page column 32-33
[4] Patent: US2014/213571, 2014, A1. Location in patent: Paragraph 0223

2,6-dichloropyridin-3-ol(52764-11-1)Related Product Information

• 2,6-Dichloro-3-methylpyridine
• 2,6-diaminoTryptycene
• 2,6-dimethoxyanthracene
• 2,6-DICHLORO-4-METHYLQUINOLINE
• 2,6-DIFLUORONICOTINALDEHYDE
• 1-(2,6-dichloropyridin-3-yl)ethanone
• 2,6-Dichloro-3-iodopyridine
• 2,6-Dichloro-4-iodophenol
• 2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylic acid(SALTDATA: FREE)
• 2,6-DICHLOROPYRIDINE-3,4-DIAMINE
• 2,6-Difluoro-3-iodopyridine
• 2,6-dichloro-3-Methoxypyridine
• METHYL 2,6-DIFLUORONICOTINATE
• 3-Pyridinol,2,6-difluoro-(9CI)
• 2,6-DICHLORO-3-HYDROXYPYRIDINE-4-CARBOXALDEHYDE
• 2,6-DICHLORO-3-HYDROXYPYRIDINE-4-CARBOXYLIC ACID
• 3-Pyridinamine,2,6-dichloro-5-methoxy-(9CI)
• 2,6-dichloropyridin-3-ol