2-Chloro-3-hydroxypyridine Chemical Properties

Melting point:

170-172 °C (lit.)

Boiling point:

316.2±22.0 °C(Predicted)

Density 

1.2309 (rough estimate)

refractive index 

1.4510 (estimate)

storage temp. 

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

pka

4.32±0.10(Predicted)

form 

Powder

color 

Light beige

BRN 

2216

InChI

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

InChIKey

RSOPTYAZDFSMTN-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC=C1O

CAS DataBase Reference

6636-78-8(CAS DataBase Reference)

NIST Chemistry Reference

2-Chloro-3-pyridinol(6636-78-8)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-37/39-24/25-36

WGK Germany 

3

RTECS 

UU7707000

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:2-Chloro-3-hydroxypyridine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloro-3-hydroxypyridine Usage And Synthesis

Chemical Properties

light beige powder

Uses

2-Chloro-3-hydroxypyridine has been used in the preparation of 3-hydroxypyridine-2( 1 H)-selone. It has also been used in the synthesis of all four possible benzo[4,5]furopyridine tricyclic heterocycles: benzo[4,5]furo[2,3-b]pyridine, benzo[4,5]furo[2,3-c]pyridine, benzo[4,5]furo[3,2-c]pyridine, and benzo[4,5]furo[3,2-b]pyridine. the synthesis involves α and γ-activation of chloropyridines, as well as palladium-mediated reactions.

Synthesis

GENERAL METHOD: To a solution of 2-chloro-3-pyridyl trifluoromethanesulfonate (0.3 mmol) in anhydrous toluene (5 mL) was added Cs2CO3 (3 equiv). The reaction suspension was heated at 80 °C (oil bath temperature) with stirring for 15 hours. Upon completion of the reaction, the crude reaction mixture was quenched with ethyl acetate (~5 mL) and saturated aqueous ammonium chloride solution (~10 mL). The aqueous layer was separated and extracted with ethyl acetate (2 x 10 mL). The organic layers were combined, dried with anhydrous MgSO4 and concentrated under reduced pressure to give the crude product 2-chloro-3-hydroxypyridine. Finally, the product was purified by fast column chromatography on silica gel.

References

[1] Tetrahedron Letters, 2013, vol. 54, # 51, p. 7078 - 7079

2-Chloro-3-hydroxypyridine(6636-78-8)Related Product Information

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• 2,6-DICHLORO-3-HYDROXYPYRIDINE-4-CARBOXALDEHYDE
• 5-CHLORO-2-HYDROXYPYRIDINE-3-CARBOXYLIC ACID
• 2,6-DICHLORO-3-HYDROXYPYRIDINE-4-CARBOXYLIC ACID
• 3-BROMO-5-CHLORO-2-HYDROXYPYRIDINE