2-Bromo-5-chloro-3-nitropyridine Chemical Properties

Melting point:

75-78°C

Boiling point:

250.3±35.0 °C(Predicted)

Density 

1.936±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

soluble in Methanol

pka

-5.53±0.20(Predicted)

form 

Solid

color 

Off-white

InChI

InChI=1S/C5H2BrClN2O2/c6-5-4(9(10)11)1-3(7)2-8-5/h1-2H

InChIKey

VFMIDVIAQMFGGP-UHFFFAOYSA-N

SMILES

C1(Br)=NC=C(Cl)C=C1[N+]([O-])=O

CAS DataBase Reference

75806-86-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-38-22

Safety Statements 

26-36/37/39-39

WGK Germany 

3

HazardClass 

IRRITANT

HazardClass 

6.1

HS Code 

2933399990

2-Bromo-5-chloro-3-nitropyridine Usage And Synthesis

Chemical Properties

Hoar or pale yellow solid

Synthesis

To a solution of 2-Amino-5-chloro-3-nitropyridine (10.0 g, 57.6 mmol) in HBr [(31.0 mL (100%), 286.4 mmol)], sodium nitrite (13.8 g, 199.9 mmol) was added dropwise. To the stirred solution, Br2 (10.0 mL, 197.1 mmol)in water was added and stirred at room temperature for 1 h. The reaction mixture was basified with NaHCO3 solution (PH=7), extracted with ethyl acetate, washed with water, and dried over anhydrous Na2SO4. The solvent was removed under vacuum to yield 2-Bromo-5-chloro-3-nitropyridine (10.0 g, 73.0%) as a yellow solid.

References

[1] Patent: WO2014/202580, 2014, A1. Location in patent: Page/Page column 100
[2] Patent: WO2014/202528, 2014, A1. Location in patent: Page/Page column 97
[3] Synthetic Communications, 2012, vol. 42, # 19, p. 2791 - 2796
[4] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 8, p. 2061 - 2071
[5] Patent: US5801183, 1998, A

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