2,5-Dichloronicotinonitrile Chemical Properties

Melting point:

118-119℃

Boiling point:

255℃

Density 

1.49

Flash point:

108℃

storage temp. 

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

pka

-4.56±0.10(Predicted)

Appearance

White to light brown Solid

InChI

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

InChIKey

CZKCARRNABGWOH-UHFFFAOYSA-N

SMILES

C(#N)C1=C(Cl)N=CC(Cl)=C1

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

2,5-Dichloronicotinonitrile Usage And Synthesis

Synthesis

The general procedure for the synthesis of 2,5-dichloronicotinonitrile from 2,5-dichloronicotinamide was as follows: 2,5-dichloronicotinamide (180 mg, 0.94 mmol) was dissolved in dichloromethane (8.0 mL). Subsequently, trifluoroacetic anhydride (0.16 mL, 1.20 mmol) and triethylamine (0.30 mL, 2.20 mmol) were sequentially added to the reaction system and the reaction mixture was stirred. After the reaction was completed, the reaction solution was slowly poured into water (50 mL). The aqueous phase was extracted with dichloromethane (80 mL x 3) and the organic phase was combined. The organic phase was washed with saturated saline (150 mL) and dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/petroleum ether) to give 2,5-dichloronicotinonitrile (155 mg, 95% yield) as a white solid.

References

[1] Patent: CN108276401, 2018, A. Location in patent: Paragraph 0475; 0507; 0508
[2] Patent: WO2018/127096, 2018, A1. Location in patent: Paragraph 00260
[3] Patent: CN108727369, 2018, A. Location in patent: Paragraph 0607; 0622-0624