3-Bromo-5-iodo-pyridine Chemical Properties

Melting point:

127-131 °C

Boiling point:

266.5±25.0 °C(Predicted)

Density 

2.347±0.06 g/cm3(Predicted)

storage temp. 

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

pka

0.85±0.20(Predicted)

form 

Solid

color 

Off-white

Water Solubility 

Slightly soluble in water.

Sensitive 

Light Sensitive

InChI

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

InChIKey

AOOZLVWDZUPEHT-UHFFFAOYSA-N

SMILES

C1=NC=C(I)C=C1Br

CAS DataBase Reference

233770-01-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-22

Safety Statements 

26-36/37/39

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

IRRITANT

HS Code 

2933399990

3-Bromo-5-iodo-pyridine Usage And Synthesis

Chemical Properties

Off-white Cryst

Uses

Reactant in the synthesis chiral 4, 4?-Bipyridines. 3-bromo-5-(trifluoromethyl)pyridine is prepared from 3-Bromo-5-iodopyridine.

Synthesis

General procedure for the synthesis of 3-bromo-5-iodopyridine from 3,5-dibromopyridine: 3,5-dibromopyridine (0.52 g, 2.19 mmol) was dissolved in anhydrous tetrahydrofuran (4 mL) at -10 °C, keeping the internal temperature below -5 °C. Subsequently, tetrahydrofuran solution of 2M isopropylmagnesium chloride (0.25 g, 2.11 mmol) and anhydrous tetrahydrofuran solution of iodine (0.62 g, 2.11 mmol) were added sequentially and slowly and stirred for about 5 minutes. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and saturated aqueous sodium bisulfite. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated to afford 3-bromo-5-iodopyridine (4.85 g, 98% yield), which can be used directly for further purification. The product characterization data were as follows: 1H NMR (400 MHz, CDCl3) δ 7.54-7.51 (m, 1H), 8.26 (s, 1H), 8.42 (s, 1H); MS (ES): m/z = 284 [M + H]+.

References

[1] Patent: WO2005/94822, 2005, A1. Location in patent: Page/Page column 35
[2] Chemistry - A European Journal, 2010, vol. 16, # 41, p. 12425 - 12433
[3] European Journal of Organic Chemistry, 2002, # 2, p. 327 - 330
[4] Patent: US2006/4018, 2006, A1. Location in patent: Page/Page column 12; 27
[5] Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 1062,1068

3-Bromo-5-iodo-pyridine(233770-01-9)Related Product Information

• 2-Chloro-3-hydroxypyridine
• 2-Bromo-5-nitropyridine
• 3-Bromo-5-chloropyridine
• Pyridine
• 3-Pyridyl bromide
• 3-Hydroxypyridine
• 3-Bromo-5-fluoropyridine
• 1-Hexadecylpyridinium bromide
• 3-Aminopyridine
• 3-Bromo-2-fluorobenzoic acid
• 3-BROMO-5-HYDROXYBENZOIC ACID
• 3-Bromo-6-chloroimidazo[1,2-b]pyridazine
• 3-BROMO-2-FLUOROBENZOTRIFLUORIDE
• 3-BROMO-5-ISOXAZOLECARBOXALDEHYDE
• 3-Bromo-4-chlorofuro[3,2-c]pyridine
• 5-TERT-BUTYL METHYLISOPHTHALATE
• 3-BROMO-5-FLUOROBENZYL ALCOHOL
• methyl 3-bromopicolinate