2,3-DICHLORO-5-NITROPYRIDINE Chemical Properties

Melting point:

51-56℃

Boiling point:

256°C(lit.)

Density 

1.629±0.06 g/cm3(Predicted)

Flash point:

>110°C

storage temp. 

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

solubility 

soluble in Methanol

form 

powder to crystal

pka

-4.99±0.10(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C5H2Cl2N2O2/c6-4-1-3(9(10)11)2-8-5(4)7/h1-2H

InChIKey

XLPDVAVQKGDHNO-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C([N+]([O-])=O)C=C1Cl

CAS DataBase Reference

22353-40-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-43-41-37/38-25

Safety Statements 

26-36/37/39-45-39

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

1

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29333990

2,3-DICHLORO-5-NITROPYRIDINE Usage And Synthesis

Uses

5-Nitro-2,3-Dichloropyridine is an important fine chemical intermediate, widely used in the pharmaceutical and pesticide fields.

Chemical Properties

Light yellow Cryst

Synthesis

Quinoline (48.5 mL, 0.41 mol) was slowly added to phosphorous trichloride (164.0 mL, 1.75 mol) at 0 °C and under nitrogen protection. Subsequently, 5-nitro-2-hydroxy-3-chloropyridine (204 mg, 1.17 mmol) was added to this stirred mixture. The reaction mixture was heated to 120 °C and maintained for 2 hours. After completion of the reaction, it was cooled to 0 °C and the reaction was quenched by the addition of ice water. The precipitate was collected by filtration, washed with plenty of water and dried to give 2,3-dichloro-5-nitropyridine. Yield: 220 g (97%). Melting point: 53 °C. 1H NMR (300 MHz, DMSO-d6): δ 9.16 (d, 1H, J = 2.4 Hz), 8.94 (d, 1H, J = 2.4 Hz). 13C NMR (300 MHz, DMSO-d6): δ 158.69, 137.36, 132.51, 130.13, 124.39. mass spectra ( electrospray ionization): m/z 193 ([M+H]+).

References

[1] Synthesis, 1990, # 6, p. 499 - 501
[2] European Journal of Medicinal Chemistry, 2012, vol. 58, p. 355 - 360
[3] Patent: WO2013/117963, 2013, A1. Location in patent: Page/Page column 21
[4] Patent: WO2014/207508, 2014, A1. Location in patent: Page/Page column 55
[5] Roczniki Chemii, 1968, vol. 42, p. 2079,2084

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