2-Bromo-6-hydroxypyridine Chemical Properties

Melting point:

121.0 to 125.0 °C

Boiling point:

336.6±42.0 °C(Predicted)

Density 

1.776±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

7.33±0.10(Predicted)

color 

White to Light yellow to Purple

InChI

InChI=1S/C5H4BrNO/c6-4-2-1-3-5(8)7-4/h1-3H,(H,7,8)

InChIKey

VOMMPWVMVDGZEM-UHFFFAOYSA-N

SMILES

C1(=O)NC(Br)=CC=C1

CAS DataBase Reference

27992-32-1

Safety Information

HS Code 

2933399990

2-Bromo-6-hydroxypyridine Usage And Synthesis

Synthesis Reference(s)

Synthesis, p. 707, 1974 DOI: 10.1055/s-1974-23407

Synthesis

General procedure for the synthesis of 2-bromo-6-hydroxypyridine from 2,6-dibromopyridine: 2,6-dibromopyridine (4 g, 17 mmol), potassium tert-butoxide (20 g, 0.27 mol), and redistilled tert-butanol (100 mL) were mixed and reacted at reflux overnight. After completion of the reaction, the mixture was cooled and the solvent was removed under vacuum. Subsequently, the ice-water mixture was carefully added and the aqueous layer was extracted with chloroform (100 mL x 2) to remove unreacted starting material. Next, the aqueous layer was acidified with 3N hydrochloric acid and again extracted with chloroform (100 mL x 2). The organic phases were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated to give pure 2-bromo-6-hydroxypyridine (2.5 g, 85% yield) as a white solid.

References

[1] Patent: US2009/318455, 2009, A1. Location in patent: Page/Page column 82
[2] Synlett, 2015, vol. 26, # 11, p. 1557 - 1562
[3] Patent: WO2014/57103, 2014, A1. Location in patent: Page/Page column 174
[4] Tetrahedron, 1996, vol. 52, # 35, p. 11385 - 11404
[5] Tetrahedron, 1996, vol. 52, # 35, p. 11385 - 11404

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