ChemicalBook--->CAS DataBase List--->21855-16-3

21855-16-3

21855-16-3 Structure

21855-16-3 Structure
IdentificationBack Directory
[Name]

Ethyl2,6-PyridinedicarboxylateMono
[CAS]

21855-16-3
[Synonyms]

6-(Ethoxycarbonyl)
Methyl dipicolinate
6-(Ethoxycarbonyl)picolinic acid
Ethyl2,6-PyridinedicarboxylateMono
2,6-pyridinedicarboxylatemonoethylester
6-Ethoxycarbonyl-2-pyridinecarboxylic acid
2,6-Pyridinedicarboxylic acid, 2-ethyl ester
2,6-pyridinediCarbocylic acid monoethyl ester
[Molecular Formula]

C9H9NO4
[MDL Number]

MFCD00806154
[MOL File]

21855-16-3.mol
[Molecular Weight]

195.17
Chemical PropertiesBack Directory
[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
Safety DataBack Directory
[HS Code ]

2933399990
Spectrum DetailBack Directory
[Spectrum Detail]

Ethyl2,6-PyridinedicarboxylateMono(21855-16-3)1HNMR
Hazard InformationBack Directory
[Synthesis]

2,6-Pyridinedicarboxylic acid chloride

3739-94-4

Ethanol

64-17-5

Diethyl 2,6-pyridinedicarboxylate

15658-60-3

Ethyl2,6-PyridinedicarboxylateMono

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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15658-60-3

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