2,5-PYRIDINEDICARBOXYLIC ACID DIETHYL ESTER Chemical Properties

Melting point:

46 °C

Boiling point:

181 °C / 17mmHg

Density 

1.165±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

-0.10±0.10(Predicted)

color 

White to Gray to Brown

Safety Information

HS Code 

2933.39.9200

2,5-PYRIDINEDICARBOXYLIC ACID DIETHYL ESTER Usage And Synthesis

Synthesis

Concentrated sulfuric acid (3.9 mL, 71.6 mmol) was slowly added dropwise to a stirred suspension of 2,5-pyridinedicarboxylic acid (3.0 g, 17.9 mmol) in anhydrous ethanol (10 mL) over 15 minutes. Subsequently, the reaction mixture was heated to reflux for 18 hours. Upon completion of the reaction, the solution was cooled to room temperature and the solvent was removed by evaporation under reduced pressure. Saturated sodium bicarbonate (NaHCO3) solution was added to the residue and the pH was adjusted to 7-8. Next, the aqueous phase was extracted with ethyl acetate (EtOAc, 4 x 50 mL). All organic extracts were combined and washed with brine (30 mL) and subsequently dried with anhydrous sodium sulfate (Na2SO4). Finally, the solvent was evaporated under reduced pressure to afford diethyl 2,5-pyridinedicarboxylate (3.0 g, 75% yield), which could be used for subsequent experiments without further purification.

References

[1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 24, p. 3025 - 3028
[2] Journal of Porphyrins and Phthalocyanines, 2010, vol. 14, # 6, p. 469 - 480
[3] Dalton Transactions, 2015, vol. 44, # 35, p. 15391 - 15395
[4] European Journal of Organic Chemistry, 2010, # 1, p. 174 - 182
[5] CrystEngComm, 2011, vol. 13, # 8, p. 2915 - 2922

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