4,6-DICHLORONICOTINONITRILE Chemical Properties

Melting point:

133-135°

Boiling point:

272.9±35.0℃ (760 Torr)

Density 

1.49±0.1 g/cm3 (20 ºC 760 Torr)

Flash point:

118.8±25.9℃

storage temp. 

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

pka

-1.94±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C6H2Cl2N2/c7-5-1-6(8)10-3-4(5)2-9/h1,3H

InChIKey

VNRGFXKFARXGSX-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=CC(Cl)=C1C#N

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN2811

HazardClass 

IRRITANT

HS Code 

2933399990

4,6-DICHLORONICOTINONITRILE Usage And Synthesis

Uses

4, 6-dichlorotinonitrile is a nitrile organic compound, which can be used as pharmaceutical intermediates.

Synthesis

General procedure for the synthesis of 4,6-dichloronicotinonitrile from 4,6-dichloropyridine-3-amide: Pyridine (20.3 mL, 250 mmol) was slowly added to an acetonitrile (180 mL) suspension of 4,6-dichloronicotinamide (8.00 g, 41.9 mmol) at room temperature. Subsequently, phosphorous trichloride (11.7 mL, 126 mmol) was added dropwise over 3 minutes. The reaction mixture was heated to 60 °C with continuous stirring for 1.5 hours. Upon completion of the reaction, the solution was cooled to room temperature and carefully poured into 0.8 M aqueous sodium hydroxide solution (600 mL). Multiple extractions were performed with ethyl acetate (6 x 400 mL) and the organic phases were combined. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel fast column chromatography (30% ethyl acetate/hexane as eluent) to afford 4,6-dichloronicotinonitrile as a light orange solid (6.41 g, 88% yield).1H NMR (400 MHz, CDCl3) δ 8.67 (s, 1H), 7.58 (s, 1H).

References

[1] Patent: US2015/291629, 2015, A1. Location in patent: Paragraph 1175

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