2,6-Dichloro-3-nitropyridine Chemical Properties

Melting point:

55-60 °C(lit.)

Boiling point:

295.5±35.0 °C(Predicted)

Density 

1.6791 (rough estimate)

refractive index 

1.6100 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

Liquid

pka

-5.76±0.10(Predicted)

color 

Clear colorless to light yellow

BRN 

1619741

InChI

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

InChIKey

SHCWQWRTKPNTEM-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

16013-85-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-42/43-43

Safety Statements 

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

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:2,6-Dichloro-3-nitropyridine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,6-Dichloro-3-nitropyridine Usage And Synthesis

Chemical Properties

yellow crystalline powder or chunks

Uses

2,6-Dichloro-3-nitropyridine was used:

• in the synthesis of pyridyldifluoroacetates
• as starting reagent in the preparation of bicyclooxacalixhetarene

Definition

Nitropyridine nucleus played a pivotal role in the development of different medicinal agents and in the field of agrochemicals. It is seen from the current literature that pyridine derivatives have been developed and used as insecticidal agents. Nitrated pyridines and their derivatives are important intermediates in synthesis of heterocyclic compounds in dyes and pharmaceutical products. Fused heterocycles containing nitropyridine systems have been associated with several biological and medicinal activities including antiolytic, antiviral and anti-inflammatory profiles.

General Description

2,6-Dichloro-3-nitropyridine undergoes macrocyclic condensation reaction with resorcinol derivatives to yield chiral tetraoxacalix[2]arene[2]pyridines.

Synthesis

General procedure for the synthesis of 2,6-dichloro-3-nitropyridine from 2,6-dichloropyridine: 80 mL of concentrated sulfuric acid was added to a 150 mL three-necked flask with stirring at room temperature, and 7.4 g (0.05 mol) of 2,6-dichloropyridine (IV) was slowly added, followed by the slow addition of 10.1 g (0.1 mol) of potassium nitrate. After the addition was completed, stirring was continued for 30 minutes, then the temperature was slowly increased to 120°C and the reaction was maintained at this temperature for 10 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature and poured into crushed ice with stirring. The precipitated white solid precipitate was washed to neutrality with ice water, immediately subjected to diafiltration, and dried to give 7.75 g of white solid 2,6-dichloro-3-nitropyridine (V) in 80% yield and melting point of 61-63 °C.

Structure and conformation

The asymmetric unit of 2,6-Dichloro-3-nitropyridine consists of two crystallographically independent mol-ecules. The pyridine ring in each mol-ecule is essentially planar, with maximum deviations of 0.004 (4) and 0.007 (4)Å. Short Cl-O [3.09?(3) and 3.13 (4)Å] and Cl-Cl [3.38 (12)Å] contacts were observed. No significant inter-molecular inter-actions were observed in the crystal packing.

References

[1] Patent: CN103936766, 2016, B. Location in patent: Paragraph 0032-0033
[2] Patent: US2006/80790, 2006, A1. Location in patent: Page/Page column 2
[3] Patent: WO2017/31176, 2017, A1. Location in patent: Page/Page column 33-34
[4] Journal of Heterocyclic Chemistry, 1984, vol. 21, # 5, p. 1521 - 1525
[5] ChemMedChem, 2015, vol. 10, # 2, p. 368 - 379

2,6-Dichloro-3-nitropyridine(16013-85-7)Related Product Information

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