2-Chloro-3-nitropyridine Chemical Properties

Melting point:

100-103 °C (lit.)

Boiling point:

260.3±20.0 °C(Predicted)

Density 

1.6616 (rough estimate)

refractive index 

1.454-1.456

Flash point:

185°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

Water Solubility 

Insoluble in water

pka

-2.60±0.10(Predicted)

form 

Crystalline Powder

color 

Yellow

BRN 

124482

InChI

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

InChIKey

UUOLETYDNTVQDY-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

5470-18-8(CAS DataBase Reference)

NIST Chemistry Reference

2-Chloro-3-nitropyridine(5470-18-8)

EPA Substance Registry System

Pyridine, 2-chloro-3-nitro- (5470-18-8)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/22-36/37/38-22

Safety Statements 

22-24/25-37/39-26-36

RIDADR 

UN 2811

WGK Germany 

3

TSCA 

T

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29333999

MSDS

• Language:English Provider:2-Chloro-3-nitropyridine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloro-3-nitropyridine Usage And Synthesis

Chemical Properties

yellow crystalline powder

Uses

2-Chloro-3-nitropyridine is often used as a pharmaceutical intermediate.

Reactions

2-Chloro-3-nitropyridine is a nucleophilic compound that reacts with amines to form substituted amines.

Synthesis

General procedure for the synthesis of 2-chloro-3-nitropyridine from 3-nitropyridine-2-carboxylic acid: accurately weigh 3-nitropyridine-2-carboxylic acid (50.4 mg, 0.3 mmol), sodium carbonate (64.0 mg, 0.6 mmol), sodium chloride (17.6 mg, 0.3 mmol) and tert-butyl hypochlorite (32 μL, 0.3 mmol) in a 25 mL Schlenk reaction flask. Subsequently, dichloromethane (3 mL) was added as a solvent and the reaction mixture was placed in an oil bath at 25 °C for 20 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using petroleum ether/ethyl acetate as eluent to give 2-chloro-3-nitropyridine in 58% yield.

Purification Methods

It forms needles from H2O. Purify it by continuous sublimation over a period of 2 weeks at 50-60o/0.1mm [Barlin J Chem Soc 2150 1964]. The N-oxide has m 100o(from CH2Cl2/Et2O). [Taylor & Driscoll J Org Chem 25 1716 1960, Ochiai & Kaneko Chem Pharm Bull Jpn 8 28 1960, Beilstein 20/5 V 451.]

References

[1] Patent: CN108586334, 2018, A. Location in patent: Paragraph 0060-0062

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