6-CHLORO-2-CYANO-3-NITROPYRIDINE Chemical Properties

Melting point:

118-120 °C

Boiling point:

347.2±42.0 °C(Predicted)

Density 

1.57±0.1 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

-10.14±0.10(Predicted)

Appearance

White to light yellow Solid

InChI

InChI=1S/C6H2ClN3O2/c7-6-2-1-5(10(11)12)4(3-8)9-6/h1-2H

InChIKey

XVIHGTRTKQZJAC-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

93683-65-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

RIDADR 

UN2811

HazardClass 

IRRITANT

HS Code 

2933399990

6-CHLORO-2-CYANO-3-NITROPYRIDINE Usage And Synthesis

Chemical Properties

Light yellow Cryst

Synthesis

General procedure for the preparation of 2-cyano-3-nitro-6-chloropyridine: 1. 2,6-dichloro-3-nitropyridine (5.0 g, 25.9 mmol) and cuprous(I) cyanide (2.55 g, 28.5 mmol) were mixed in N-methylpyrrolidone (19 mL). 2. the mixture was heated to 180 °C and maintained for 15 min. 3. After completion of the reaction, cooled to room temperature, the reaction mixture was poured into ice water and stirred for 10 minutes. 4. The aqueous layer was separated and the organic layer was extracted with boiling toluene followed by re-extraction with ethyl acetate. 5. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. 6. The residue was ground with ether and filtered to give 2-cyano-3-nitro-6-chloropyridine (1.76 g, 39% yield). 1H-NMR (CDCl3, 300MHz) data: δ 7.78 (d, J = 8.9Hz, 1H), 8.54 (d, J = 8.9Hz, 1H).

References

[1] Journal of Heterocyclic Chemistry, 1984, vol. 21, # 5, p. 1521 - 1525
[2] Patent: WO2005/97805, 2005, A1. Location in patent: Page/Page column 48-49
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 23, p. 4533 - 4541

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