5-Bromo-2-chloropyridine Chemical Properties

Melting point:

65-69 °C (lit.)

Boiling point:

208.1±20.0 °C(Predicted)

Density 

1.7783 (rough estimate)

refractive index 

1.5400 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

-2.25±0.10(Predicted)

form 

Crystalline Powder or Crystals

color 

Off-white

BRN 

108887

InChI

InChI=1S/C5H3BrClN/c6-4-1-2-5(7)8-3-4/h1-3H

InChIKey

PEAOEIWYQVXZMB-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(Br)C=C1

CAS DataBase Reference

53939-30-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39-36/37/39

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

T

HazardClass 

IRRITANT, IRRITANT-HARMFUL

HS Code 

29333990

MSDS

• Language:English Provider:5-Bromo-2-chloropyridine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Bromo-2-chloropyridine Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

5-Bromo-2-chloropyridine may be used in the preparation of following compounds:

• Amino-2-chloropyridine via palladium-catalyzed amination.
• 5-Bromo-2-fluoropyridine via halogen-exchange reaction using anhydrous potassium fluoride.
• 2-Chloro-5-(2,5-dimethoxyphenyl)pyridine via Suzuki coupling with 2,5-dimethoxyphenylboronic acid.

Synthesis

6-Chloro-pyridin-3-ylamine was dissolved slowly with constant stirring in 48% HBr solution (50 mL) at r.t. and then the solution was cooled to -10 °C. A solution of sodium nitrite in cold water was added dropwise at -10 °C with constant stirring over 2 h, followed by a solution of copper (I) bromide in 48% HBr dropwise. The mixture was then stirred at r.t. until complete. The mixture was neutralized with sodium carbonate and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (60-120 mesh) eluting with 1% ethyl acetate/petroleum ether to afford 5- bromo-2-chloropyridine.

References

[1] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3627 - 3644
[2] Patent: WO2008/62182, 2008, A1. Location in patent: Page/Page column 119
[3] Patent: WO2004/6922, 2004, A1. Location in patent: Page/Page column 53
[4] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1920, vol. 50, p. 476
[5] Chem. Zentralbl., 1923, vol. 94, # III, p. 1020

5-Bromo-2-chloropyridine(53939-30-3)Related Product Information

• 1-Hexadecylpyridinium bromide
• 2-Chloro-5-chloromethylpyridine
• Clopidol
• 2-Chloro-5-fluoropyridine
• 2-Chloro-3-cyanopyridine
• 5-Amino-2-chloropyridine
• 2-chloro-5-cyanopyridine
• 3-Bromo-6-chloro-2-methylpyridine
• 6-Chloro-2-methyl-3-nitropyridine
• 2-Chloro-5-hydroxypyridine
• 2-CHLORO-5-METHOXYPYRIDINE
• 2-Chloro-5-nitropyridine
• 2-Chloro-5-iodopyridine
• 5-Bromo-2-chlorobenzoic acid
• pyridinium Chlorochromate
• Difluorochloromethane
• Bromine
• 2-Chloropyridine