2-Bromo-5-chloropyridine Chemical Properties

Melting point:

65-69 °C

Boiling point:

128 °C / 16mmHg

Density 

1.736±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

-1.49±0.10(Predicted)

form 

Powder

color 

Beige to yellow-brown

Water Solubility 

Slightly soluble in water.

InChI

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

InChIKey

BZUUVQCSPHPUQA-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

40473-01-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-20/22-20/2236/37/38-20/21/22

Safety Statements 

36/37/39-26-22-22 26 36/37/39-36

RIDADR 

Cool, dry,tightly closed

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

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2-Bromo-5-chloropyridine Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

It is an important organic intermediate used in agrochemicals, pharmaceuticals and dyestuff fields. It is also used in the synthesis of novel halopyridinylboronic acids and esters.

Synthesis

General procedure for the synthesis of 2-bromo-5-chloropyridine from 2-amino-5-chloropyridine: [Ref. Example 25] 5-(5-chloro-2-pyridinyl)-1-(3-pyridinyl)-1H-pyrazole-3-carboxylic acid; [show image] 1) Hydrogen bromide (12 ml, 47% aqueous solution) was slowly added to hydrogen bromide (12 ml, 47% aqueous solution) at 0 °C in a hydrobromic acid containing 2-amino-5-chloropyridine (5 g) ( 50 ml, 47%) solution. Subsequently, a solution of sodium nitrite (15 g) dissolved in water (20 ml) was added dropwise to the reaction mixture. The reaction solution was stirred at 0°C for 1 h. After that, a solution of sodium hydroxide (32 g) in water (80 ml) and ethyl acetate was added for extraction. The organic and aqueous phases were separated and the organic phase was dried over anhydrous sodium sulfate. After filtration, the solvent was removed by concentration under reduced pressure to give 2-bromo-5-chloropyridine (6.8 g, 91% yield) as a white solid. The product was characterized by 1H-NMR (400 MHz, CDCl3): δ 7.44 (1H, d, J = 8.42 Hz), 7.54 (1H, m), 8.36 (1H, s).

References

[1] Chemistry of Heterocyclic Compounds, 2017, vol. 53, # 2, p. 196 - 206
[2] Khim. Geterotsikl. Soedin., 2017, vol. 53, # 2, p. 196 - 206,11
[3] Patent: EP1698626, 2006, A1. Location in patent: Page/Page column 41
[4] Patent: EP1762568, 2007, A1. Location in patent: Page/Page column 24-25
[5] Patent: US5750545, 1998, A

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