Basic information Safety Supplier Related

Ethyl2,6-PyridinedicarboxylateMono

Basic information Safety Supplier Related

Ethyl2,6-PyridinedicarboxylateMono Basic information

Product Name:
Ethyl2,6-PyridinedicarboxylateMono
Synonyms:
  • 6-Ethoxycarbonyl-2-pyridinecarboxylic acid
  • Methyl dipicolinate
  • 2,6-pyridinediCarbocylic acid monoethyl ester
  • 6-(Ethoxycarbonyl)
  • Ethyl2,6-PyridinedicarboxylateMono
  • 2,6-pyridinedicarboxylatemonoethylester
  • 6-(Ethoxycarbonyl)picolinic acid
  • 2,6-Pyridinedicarboxylic acid, 2-ethyl ester
CAS:
21855-16-3
MF:
C9H9NO4
MW:
195.17
Mol File:
21855-16-3.mol
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Ethyl2,6-PyridinedicarboxylateMono Chemical Properties

Melting point:
116-117℃
Boiling point:
396.2±27.0 °C(Predicted)
Density 
1.304±0.06 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
pka
3.27±0.10(Predicted)
Appearance
White to off-white Solid
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Safety Information

HS Code 
2933399990
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Ethyl2,6-PyridinedicarboxylateMono Usage And Synthesis

Synthesis

3739-94-4

64-17-5

15658-60-3

21855-16-3

The general synthetic procedure was as follows. 2,6-Pyridinedicarboxylic acid (1, 1.5 g, 8.98 mmol) was mixed with 24 mL of dichlorosulfoxide (SOCl2). The reaction mixture was heated to reflux for 3 hours. After completion of the reaction, excess dichlorosulfoxide was removed by distillation under reduced pressure. To the resulting white solid, 50 mL of tetrahydrofuran (THF) was added. After the solid was completely dissolved, ethanol (10.5 mmol) and N,N-diisopropylethylamine (DIEA, 10.5 mmol) were added slowly via syringe. The reaction mixture was heated to reflux for 4 hours. At the end of the reaction, the solvent was removed by distillation under reduced pressure. The residue was separated and purified by column chromatography to afford the target products diethyl 2,6-pyridinedicarboxylate and monoethyl 2,6-pyridinedicarboxylate.

References

[1] Tetrahedron, 2011, vol. 67, # 44, p. 8458 - 8464

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