2-Chloro-4-nitropyridine Chemical Properties

Melting point:

52-56 °C (lit.)

Boiling point:

258.4±20.0 °C(Predicted)

Density 

1.489±0.06 g/cm3(Predicted)

Flash point:

223 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

-1.93±0.10(Predicted)

form 

crystalline powder

color 

Yellow

BRN 

120418

InChI

InChI=1S/C5H3ClN2O2/c6-5-3-4(8(9)10)1-2-7-5/h1-3H

InChIKey

LIEPVGBDUYKPLC-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

23056-36-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:2-Chloro-4-nitropyridine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloro-4-nitropyridine Usage And Synthesis

Chemical Properties

Light yellow powder

Uses

2-Chloro-4-nitropyridine may be used to synthesize 2-chloro-4-ethoxypyridine and 4-thiophenoxypyridines.

Uses

2-Chloro-4-nitropyridine is used in the preparation of (thio)barbituric acid derivatives in the treatment of obesity related non-alcoholic fatty liver disease. As well it is used in the production of selective and potent MET Kinase inhibitors.

Synthesis

The general procedure for the synthesis of 2-chloro-4-nitropyridine-N-oxide from 2-chloro-4-nitropyridine-N-oxide is as follows: referring to the method of Example 17, phosphorus trichloride (4.2 mL, 48.7 mmol) was slowly added to a solution of anhydrous chloroform (25 mL) of 2-chloro-4-nitropyridine-N-oxide (1.70 g, 9.74 mmol) at room temperature. Subsequently, the reaction mixture was heated to reflux and maintained at this temperature for the reaction overnight. Upon completion of the reaction, the mixture was cooled to room temperature. The reaction solution was carefully poured into ice water and the pH was adjusted to 7-8 with alkali and subsequently washed with saturated sodium bicarbonate solution. The aqueous phase was extracted twice with chloroform, all organic phases were combined, washed sequentially with water and brine, dried over anhydrous sodium sulfate, filtered and the organic phase was concentrated. Finally, the product was dried under high vacuum to give 2-chloro-4-nitropyridine (1.2 g, 78% yield) as a solid.

References

[1] Journal of Organic Chemistry, 2009, vol. 74, # 19, p. 7441 - 7448
[2] Patent: WO2008/62182, 2008, A1. Location in patent: Page/Page column 114
[3] Journal of the American Chemical Society, 1959, vol. 81, p. 2674

2-Chloro-4-nitropyridine(23056-36-2)Related Product Information

• 2-Bromo-5-nitropyridine
• 4-Nitropyridine
• Pentachloropyridine
• 1-Chloro-3-nitrobenzene
• 2-Chloro-5-chloromethylpyridine
• 2-Chloro-3-hydroxypyridine
• Clopidol
• 2-Chloro-4-picoline
• 4-Chloronitrobenzene
• Difluorochloromethane
• 2-CHLORO-3-FLUORO-4-NITROPYRIDINE N-OXIDE
• 2,6-Dichloro-3-nitropyridine
• 2,6-DICHLORO-4-NITROPYRIDINE-N-OXIDE
• 2-CHLORO-4-NITROPYRIDINE-N-OXIDE,2-CHLORO-4-NITROPYRIDINE 1-OXIDE,2-Chloro-4-nitropyridine-N-oxide ,97%
• 4-Nitrobenzyl chloride
• 2,4-Dichloro-3-nitropyridine
• 4-Chloro-3-nitropyridine hydrochloride, 97+%,4-Chloro-3-nitropyridine hydrochloride, 98+%,4-CHLORO-3-NITROPYRIDINE HYDROCHLORIDE, 90+%
• 2-Nitrochlorobenzene