5-Bromo-2-iodopyridine Chemical Properties

Melting point:

113-117 °C (lit.)

Boiling point:

258.8±20.0 °C(Predicted)

Density 

2.347±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO, Methanol (Slightly)

pka

-0.51±0.10(Predicted)

form 

Crystalline Powder

color 

White to beige

Sensitive 

Light Sensitive

BRN 

2119

Stability:

Light Sensitive

InChI

InChI=1S/C5H3BrIN/c6-4-1-2-5(7)8-3-4/h1-3H

InChIKey

HSNBRDZXJMPDGH-UHFFFAOYSA-N

SMILES

C1(I)=NC=C(Br)C=C1

CAS DataBase Reference

223463-13-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, LIGHT SENSITIVE

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Bromo-2-iodopyridine Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

5-Bromo-2-iodopyridine may be used in the synthesis of the following:

• 5-bromopyridyl-2-magnesium chloride via reaction with isopropylmagnesium chloride solution
• 5-bromo-2-pyridylzinc iodide via treatment with active zinc in tetrahydrofuran
• 5-bromo-2-(trifluoromethyl)pyridine via halogen/trifluoromethyl displacement reaction
• (5-bromopyridin-2-yl)zinc(II) chloride via multi-step synthesis
• 5,5′-dibromo-2,2′-bipyridine via multi-step synthesis

Synthesis

The general procedure for the synthesis of 5-bromo-2-iodopyridine from 2,5-dibromopyridine was as follows: an aqueous solution of 57% hydriodic acid (HI) was added to a reaction system containing 2,5-dibromopyridine (12.60 g, 53.2 mmol) and sodium iodide (NaI, 11.40 g, 76 mmol). The reaction mixture was heated to reflux for 24 h, subsequently cooled to room temperature and diluted with 100 mL of water. The pH of the mixture was adjusted to alkaline with sodium bicarbonate (NaHCO3), and then treated with the addition of sodium dithionite (Na2S2O4) until the solution became colorless. The reaction mixture was extracted with dichloromethane (DCM, 5 x 60 mL), the organic phases were combined and dried over anhydrous sodium sulfate (Na2SO4). The solvent was removed by concentration under reduced pressure and the obtained residue was collected by filtration, washed with ether (Et2O, 60 mL) and dried over air to give 5-bromo-2-iodopyridine (8.28 g, 55% yield) as a light gray powder.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 17, p. 4528 - 4532
[2] Chemical Communications, 2012, vol. 48, # 8, p. 1120 - 1122
[3] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
[4] Journal of Organic Chemistry, 2001, vol. 66, # 2, p. 605 - 608
[5] Organic Letters, 2004, vol. 6, # 26, p. 4905 - 4907

5-Bromo-2-iodopyridine(223463-13-6)Related Product Information

• Chromium picolinate
• 2,2'-Bipyridine
• 2,6-Lutidine
• 1-Hexadecylpyridinium bromide
• 2-Bromo-5-nitropyridine
• 2-Chloro-3-hydroxypyridine
• 2-Iodopyridine
• 5-Bromo-2-fluorobenzoic acid
• 5-Bromo-2-chlorobenzoic acid
• 5-Bromo-2-iodo-3-methylpyridine
• Bromine
• 5-Bromo-2-iodo-4-picoline
• 5-BROMO-2-IODOPYRIDIN-3-OL
• 5-BROMO-2-IODO-3-METHOXYPYRIDINE
• 3-BROMO-2,6-DIIODO-5-METHOXYPYRIDINE
• 3,5-DIBROMO-2-IODOPYRIDINE
• 4-BROMO-1-IODOISOQUINOLINE
• 5-BROMO-2-IODOPYRIDIN-3-YL ACETATE