Chemical Properties
Yellow to red crystalline powder
Uses
Diethyl 2,6-pyridinedicarboxylate serves as a precursor for polyester synthesis via transesterification with PEG 1000[1]. It functions as a model substance to optimize esterase reactions involving lanthanide ions[2].
Synthesis
Pyridine-2,6-dicarboxylic acid (10.0g, 59.9mmol) was added into ethanol (120mL),
then 3 drops of concentrated sulfuric acid were added. The mixture was heated to
reflux for 8 hours. After evaporation of the solvent, the solid residue was washed with
saturated Na2CO3 aqueous solution and extracted with chloroform for 3 times. The
organic phase was dried with small amount of MgSO4. The solvent was removed to
afford 1 as white powder (12.6g, 56.3mmol, yield = 94%). 1
H-NMR (400MHz,
CDCl3) | ppm 8.29 (d, J = 7.80 Hz, 2H), 8.01 (t, J = 7.80, 7.80 Hz, 1H), 4.50 (q, J =
7.12, 7.12, 7.12 Hz, 2H), 1.47 (t, J = 7.13, 7.13 Hz, 3H). 13C-NMR (100 MHz, CDCl3)
| ppm 164.6, 148.6, 138.2,127.8, 62.3,14.2,14.2. ESI MS: m/z = 224.1 [M+H]+
, 246.1
[M+Na]+
.
References
[1] Soutif, J.-C., Doan, N. T., & Montembault, V. (2006). Determination by MALDI-TOF MS of the structures obtained from polytransesterification of diethyl 2,6-pyridinedicarboxylate and poly(ethylene glycol). European Polymer Journal, 42(1), 126–132.
https://doi.org/10.1016/j.eurpolymj.2005.07.026 [2] Steinkamp, T., & Karst, U. (2004). Detection scheme for bioassays based on 2,6-pyridinedicarboxylic acid derivatives and enzyme-amplified lanthanide luminescence. Analytica Chimica Acta, 526(1), 27–34.
https://doi.org/10.1016/j.aca.2004.09.060
References
[1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 9, p. 2599 - 2603
[2] Chemical Communications, 2008, # 21, p. 2444 - 2446
[3] Tetrahedron Letters, 2017, vol. 58, # 10, p. 991 - 994
[4] Molecular Crystals and Liquid Crystals, 2007, vol. 470, # 1, p. 369 - 381
[5] Organometallics, 2015, vol. 34, # 7, p. 1170 - 1176
