2-Chloro-5-hydroxypyridine Chemical Properties

Melting point:

155-158°C

Boiling point:

351.9±22.0 °C(Predicted)

Density 

1.392±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

8.69±0.10(Predicted)

color 

Light yellow to Brown

InChI

InChI=1S/C5H4ClNO/c6-5-2-1-4(8)3-7-5/h1-3,8H

InChIKey

KVCOOWROABTXDJ-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=CC=C1O

CAS DataBase Reference

41288-96-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-36-37

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

29333990

2-Chloro-5-hydroxypyridine Usage And Synthesis

Uses

2-Chloro-5-hydroxypyridine is an organic intermediate.

Chemical Properties

Light yellow Cryst

Synthesis

11B. 6-Chloropyridin-3-yl acetate (11.1 g, 64.7 mmol) from step 11a was dissolved in methanol at room temperature, followed by addition of solid potassium carbonate (4.47 g, 32.4 mmol). The reaction mixture was stirred for 2 hours and the volatiles were removed under reduced pressure. The residue was diluted with ether and water, and the aqueous phase was neutralized to pH 7 by addition of aqueous 1 N hydrochloric acid.The organic and aqueous layers were separated and the aqueous phase was extracted twice with ether. The organic extracts were combined, dried over magnesium sulfate and concentrated to give 2-chloro-5-hydroxypyridine as a white solid (8.03 g, 96% yield): melting point 155 °C; 1H NMR (CD3OD, 300 MHz) δ 7.20-7.28 (m, 2H), 7.88 (m, 1H); mass spectrum (CI/NH3) m/z: 130,132 (M+H) +; 147,149 (M+NH4)+.

References

[1] Patent: US6696439, 2004, B1. Location in patent: Page column 20
[2] Patent: US6001849, 1999, A
[3] Tetrahedron Letters, 2003, vol. 44, # 4, p. 725 - 728
[4] Patent: EP1698626, 2006, A1. Location in patent: Page/Page column 24
[5] Patent: WO2004/72072, 2004, A1. Location in patent: Page 85

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