3-Bromo-2-chloropyridine Chemical Properties

Melting point:

54-57 °C (lit.)

Boiling point:

97 °C / 10mmHg

Density 

1.7783 (rough estimate)

refractive index 

1.5400 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

pka

-0.63±0.10(Predicted)

form 

Crystalline Powder, Crystals or Flakes or Solid

color 

White to yellow

BRN 

109812

InChI

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

InChIKey

HDYNIWBNWMFBDO-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC=C1Br

CAS DataBase Reference

52200-48-3(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

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:3-Bromo-2-chloropyridine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Bromo-2-chloropyridine Usage And Synthesis

Chemical Properties

yellow Long needles

Uses

3-Bromo-2-chloropyridine may be used to synthesize:

• acetylenic dipyridone
• 3-ethynyl-2-(phenylmethoxy)-pyridine
• nemertelline
• ortho-chlorodiheteroarylamine4 or 2-chloro-N-(2,3,7-trimethylbenzo[b]thien-6-yl)pyridin-3-amine

General Description

3-Bromo-2-chloropyridine can be synthesized from 3-amino-2-chloropyridine or 2-chloro-3-pyridinamine.

Synthesis

Example 3 Synthesis of 3-bromo-2-chloropyridine (7): water (45 mL) and 48% hydrobromic acid (27 mL) were sequentially added to a reaction vial containing 3-amino-2-chloropyridine (6) (2.57 g, 20 mmol) at room temperature. Subsequently, 2,2,6,6-tetramethylpiperidine 1-yloxy (TEMPO) (0.31 g, 2 mmol) was added to the mixed solution and the reaction system was cooled to below 10 °C. A solution of sodium nitrite (4.14 g) dissolved in water (30 mL) was added slowly and dropwise. The reaction mixture was stirred at room temperature for about 2 h. After stirring, the reaction mixture was neutralized by adding a 10 mol/L aqueous sodium hydroxide solution (40 mL). The reaction mixture was extracted with toluene (300 mL in two portions) and the organic phases were combined and washed with 50 mL of water. The organic layer was concentrated under reduced pressure to remove the solvent to afford the target product 3-bromo-2-chloropyridine (7) (3.08 g, 80.1% yield).

References

[1] Patent: US2013/144061, 2013, A1. Location in patent: Paragraph 0229; 0230
[2] Journal of Organic Chemistry, 1995, vol. 60, # 5, p. 1408 - 1412

3-Bromo-2-chloropyridine(52200-48-3)Related Product Information

• 3-BROMO-2-CHLORO-4-IODOPYRIDINE
• 5-BROMO-6-CHLOROPYRIDINE-3-CARBOXYLIC ACID
• 2-Chloro-3-bromo-5-methylpyridine
• 3-Bromo-2,6-dichloropyridine
• 2-Chloro-3-bromo-5-nitropyridine
• 3-Bromo-2-chloropyridine
• 3-BROMO-2-CHLOROPYRIDINE-5-SULPHONYL CHLORIDE,3-BROMO-2-CHLOROPYRIDINE-5-SULFONYL CHLORIDE,5-BROMO-6-CHLOROPYRIDINE-3-SULFONYL CHLORIDE
• 5-AMINO-3-BROMO-2-CHLOROPYRIDINE
• 3-BROMO-2-CHLORO-4-PICOLINE
• Methyl 3-bromo-2-chloropyridine-5-carboxylate
• 3-BROMO-2-CHLORO-6-PICOLINE
• 2,5-DIBROMO-3-CHLOROPYRIDINE
• 3-BROMO-2,5-DICHLOROPYRIDINE
• 2,3-DIBROMO-6-CHLOROPYRIDINE
• 4-BROMO-3-CHLOROPYRIDINE
• 3-BROMO-2-CHLOROPYRIDINE-4-BORONIC ACID
• 2-AMINO-3-BROMO-5-CHLOROPYRIDINE
• 3,5-Dibromo-2-chloropyridine