5,6-DICHLORO-2,3-DICYANOPYRAZINE Chemical Properties

Melting point:

183 °C

Boiling point:

324.1±42.0 °C(Predicted)

Density 

1.68±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

soluble in Methanol

form 

powder to crystal

pka

-12.94±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C6Cl2N4/c7-5-6(8)12-4(2-10)3(1-9)11-5

InChIKey

QUFXYBKGILUJHS-UHFFFAOYSA-N

SMILES

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

Safety Information

RIDADR 

2811

HazardClass 

6.1

PackingGroup 

III

HS Code 

2933998090

5,6-DICHLORO-2,3-DICYANOPYRAZINE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 5,6-dichloropyrazine-2,3-dicarbonitrile from 5,6-dioxo-1,4,5,6-tetrahydropyrazine-2,3-dicarbonitrile is shown in Figure 13. The reaction should be carried out in a fume hood. A magnetically stirred slurry consisting of 8.10 g (0.050 mol) of 5,6-dioxo-1,4,5,6-tetrahydropyrazine-2,3-dicarbonitrile, 4.0 mL of dimethylformamide, and 160 mL of thionyl chloride is heated in a 500 mL round-bottomed flask equipped with 24/40 milled glass fittings under a high efficiency reflux condenser and nitrogen atmosphere. At the beginning of the reaction, the release of SO2 and HCl gas was observed at about 62°C. After about 3.5 h, the solid was completely dissolved and the temperature was raised to 70°C. Upon completion of the reaction, the reaction mixture was cooled to room temperature and subsequently placed in a dry ice/acetone bath to -65°C. The cooled slurry was rapidly filtered through a sintered-glass filter to collect the crystals formed under nitrogen protection. The solids were washed with two 50 mL portions of cold ether and air dried to give 7 g (70% yield) of 2,3-dichloro-5,6-dicyanopyrazine with a melting point of 180-182°C. If the product is darker, it can be carbonated and recrystallized by carbon treatment in 50 mL of chloroform to give 5.5 g of purified product.

References

[1] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1419 - 1421
[2] Patent: US8742107, 2014, B1. Location in patent: Page/Page column 4; 5
[3] Acta Chemica Scandinavica, 1996, vol. 50, # 12, p. 1153 - 1156
[4] Tetrahedron Letters, 2012, vol. 53, # 25, p. 3126 - 3130

5,6-DICHLORO-2,3-DICYANOPYRAZINE(56413-95-7)Related Product Information

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