3-bromo-5-chloro-2-iodopyridine Chemical Properties

Melting point:

58-60 °C(Solv: methanol (67-56-1))

Boiling point:

280.0±35.0 °C(Predicted)

Density 

2.395±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-2.80±0.20(Predicted)

Appearance

White to light yellow Solid

InChI

InChI=1S/C5H2BrClIN/c6-4-1-3(7)2-9-5(4)8/h1-2H

InChIKey

INARBABVYJQJDC-UHFFFAOYSA-N

SMILES

C1(I)=NC=C(Cl)C=C1Br

Safety Information

HS Code 

2933399990

3-bromo-5-chloro-2-iodopyridine Usage And Synthesis

Synthesis

Acetonitrile (100 mL), elemental iodine (48.9 g, 192.8 mmol), cuprous iodide (23.9 g, 125.3 mmol), and tert-butyl nitrite (14.9 g, 144.6 mmol) were sequentially added to a 500 mL three-necked flask under nitrogen protection. Under cooling in an ice bath, 2-amino-3-bromo-5-chloropyridine (20.0 g, 96.4 mmol) was slowly added, followed by heating the reaction mixture to 60 °C and stirring the reaction for 2 hours. After completion of the reaction, water (45 mL) was added to the reaction mixture and the solid was collected by filtration. The filter cake was washed with ethyl acetate (45 mL x 1) and after combining the filtrates, the aqueous phase was further extracted with ethyl acetate (200 mL x 2). The organic phases were combined, washed with saturated aqueous sodium thiosulfate (110 mL × 2) and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure, and the residue was pulped with a small amount of methanol, filtered, and dried to give 21.9 g of 3-bromo-5-chloro-2-iodopyridine white solid in 71.2% yield.

References

[1] Patent: CN106467488, 2017, A. Location in patent: Paragraph 0011; 0012; 0013; 0014; 0015; 0016-0037
[2] Tetrahedron, 2004, vol. 60, # 51, p. 11869 - 11874

3-bromo-5-chloro-2-iodopyridine(823221-97-2)Related Product Information

• 5-CHLORO-2-IODOPYRIDINE
• 2-Iodopyridine