3,4-PYRIDINEDICARBOXIMIDE

3,4-PYRIDINEDICARBOXIMIDE Property

Melting point:

232-235 °C(lit.)

Boiling point:

268.69°C (rough estimate)

Density 

1.4015 (rough estimate)

refractive index 

1.5300 (estimate)

storage temp. 

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

pka

7.80±0.20(Predicted)

form 

Crystalline Powder

color 

White to tan

InChI

InChI=1S/C7H4N2O2/c10-6-4-1-2-8-3-5(4)7(11)9-6/h1-3H,(H,9,10,11)

InChIKey

SJSABZBUTDSWMJ-UHFFFAOYSA-N

SMILES

C1=NC=CC2C(=O)NC(=O)C1=2

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

US7966000

HazardClass 

IRRITANT

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.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P405Store locked up.

3,4-PYRIDINEDICARBOXIMIDE Chemical Properties,Usage,Production

Chemical Properties

White to light brown powder

Synthesis

The general procedure for the synthesis of 3,4-pyridinedicarboxylic acid as a raw material for the synthesis of 3,4-pyridinedicarboximides was as follows: firstly, sublimated 3,4-pyridinedicarboxylic acid (50 g, 300 mmol) was suspended in acetic anhydride (123.5 g, 1,200 mmol), and heated to reflux (140-150 °C) until the solid was completely dissolved and the mixture presented homogeneous state. Subsequently, the reaction mixture was cooled and concentrated under vacuum. Next, acetamide (50 g, 846 mmol) was added to the concentrate and the mixture was heated and reacted at 140 °C for 3 hours. After completion of the reaction, the mixture was cooled to room temperature. The solid residue formed during cooling was pulverized, ground with 100 ml of water, filtered and washed with additional water. Finally, the resulting solid was dried in a desiccator to afford 3,4-pyridinedicarboximide (42.26 g, 95.1% yield), which met the purity requirements for use without further purification. The product was analyzed by LC-MS showing a m/z (ESP) of 149 [M + H]+ and a retention time (R/T) of 0.44 min.

References

[1] Patent: US2006/199804, 2006, A1. Location in patent: Page/Page column 29
[2] Acta Chimica Hungarica, 1983, vol. 112, # 4, p. 487 - 500