5-BROMO-3-IODO-PYRIDIN-2-OL Chemical Properties

Melting point:

226-227℃

Boiling point:

307.9±42.0 °C(Predicted)

Density 

2.55±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

8.52±0.10(Predicted)

Appearance

Light yellow to yellow Solid

Sensitive 

Light Sensitive

InChI

InChI=1S/C5H3BrINO/c6-3-1-4(7)5(9)8-2-3/h1-2H,(H,8,9)

InChIKey

WAUPPDAXWKLNNU-UHFFFAOYSA-N

SMILES

C1(=O)NC=C(Br)C=C1I

CAS DataBase Reference

381233-75-6

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2933399990

5-BROMO-3-IODO-PYRIDIN-2-OL Usage And Synthesis

Uses

5-BROMO-3-IODO-PYRIDIN-2-OL can be used as a pharmaceutical synthesis intermediate. It can be prepared by using 2-amino-5-bromopyridine as a reactant to prepare 2-amino-5-bromo-3-iodopyridine, followed by further diazotization; or it can be prepared by iodination using 5-bromo-2-hydroxypyridine as a reactant.

Synthesis

General procedure for the synthesis of 5-bromo-3-iodopyridin-2(1H)-one from 2-hydroxy-5-bromopyridine: 5-bromo-2-hydroxypyridine (2.5 g, 14.4 mmol), iodosuccinimide (4.7 g, 20.9 mmol), and acetonitrile (40 mL) were mixed, and the reaction was stirred for 20 min at 82 °C. After completion of the reaction, the mixture was cooled to room temperature and the solid was collected by filtration. The filter cake was recrystallized with ethyl acetate to afford the target product 5-bromo-2-hydroxy-3-iodopyridine (4.0 g) in 92.6% yield.

References

[1] Patent: CN108084186, 2018, A. Location in patent: Paragraph 0187-0188
[2] Synlett, 2003, # 11, p. 1678 - 1682
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 4, p. 1644 - 1668
[4] Patent: WO2015/132727, 2015, A1. Location in patent: Page/Page column 22; 28
[5] Heterocycles, 2002, vol. 57, # 1, p. 55 - 71

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