2,5,6-Trichloro-3-pyridinecarbonitrile Chemical Properties

Boiling point:

285.6±35.0 °C(Predicted)

Density 

1.63

storage temp. 

Inert atmosphere,Room Temperature

pka

-7.49±0.10(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C6HCl3N2/c7-4-1-3(2-10)5(8)11-6(4)9/h1H

InChIKey

FXYJHWZGUONOAL-UHFFFAOYSA-N

SMILES

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

2,5,6-Trichloro-3-pyridinecarbonitrile Usage And Synthesis

Synthesis

The general procedure for the synthesis of 2,5,6-trichloronicotinonitrile from 2,5,6-trichloropyridine-3-amide is as follows: 2,5,6-trichloronicotinamide (2.3 g, 10.2 mmol) was suspended in POCl3 (20 ml), heated to 90 °C and maintained for 1 h. The reaction was carried out in the presence of POCl3 (20 ml). Upon completion of the reaction, the mixture was cooled to room temperature and subsequently the POCl3 was removed under vacuum.The obtained residue was dissolved in dichloromethane (DCM, 50 ml) and diluted by adding ice water (50 ml). Subsequently, aqueous Na2CO3 was slowly added to adjust the pH to 8. The organic phase was separated, dried over anhydrous Na2SO4, filtered and concentrated to afford 2,5,6-trichloronicotinonitrile (2.1 g, 80% yield), which was used in the subsequent reaction without further purification.1H NMR (400 MHz, CD3OD) δ 8.54 (s, 1H).

References

[1] Patent: WO2006/82392, 2006, A1. Location in patent: Page/Page column 108
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 2958 - 2961

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