2,6-Pyridinedicarbonitrile

2,6-Pyridinedicarbonitrile Property

Melting point:

123-127 °C (lit.)

Boiling point:

290.0±20.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

-5.87±0.10(Predicted)

form 

solid

color 

Off-white to light brown

InChI

InChI=1S/C7H3N3/c8-4-6-2-1-3-7(5-9)10-6/h1-3H

InChIKey

XNPMXMIWHVZGMJ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2893-33-6

Safety

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29333990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2,6-Pyridinedicarbonitrile Chemical Properties,Usage,Production

Chemical Properties

white to off-white powder

Uses

2,6-Pyridinedicarbonitrile may be used to synthesize bis-tetrazoles and pyridine-based tridentate ligand 2,6-bis(α-aminoisopropyl)pyridine.

General Description

2,6-Pyridinedicarbonitrile is a heterocyclic dinitrile. Its biotransformation by Rhodococcus erythropolis A4 to 6-cyanopyridine-2-carboxamide has been reported.

Synthesis

The general procedure for the synthesis of 2,6-pyridinedicarbonitrile from pyridine-2,6-dicarboxylic acid was carried out as follows: liquid ammonia (0.5 ml) and acetonitrile (50 ml) were mixed in a cold bath at -40 °C, followed by the addition of pyridine-2,6-dicarboxylic acid (1.67 g). After raising the temperature of the mixture to 0°C, phosphorus pentachloride (4 g) was added in batches. The reaction mixture was stirred at room temperature for 2 hours to ensure complete reaction. After completion of the reaction, the solvent was removed by concentration under reduced pressure. The residue was dissolved with dichloromethane and subsequently washed with saturated sodium bicarbonate solution to neutrality. The organic layer was dried with anhydrous magnesium sulfate and concentrated again. The resulting solid was recrystallized by isopropanol to give white crystals of 2,6-pyridinedicarbonitrile (1.13 g) in 88% yield.

References

[1] Patent: CN105503716, 2016, A. Location in patent: Paragraph 0016
[2] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2676 - 2699
[3] Chemical Communications, 2017, vol. 53, # 42, p. 5718 - 5720