2,6-Diformylpyridine

2,6-Diformylpyridine
Names
Preferred IUPAC name
Pyridine-2,6-dicarbaldehyde
Other names
2,6-Pyridinedialdehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.024.172 Edit this at Wikidata
EC Number
  • 226-589-6
UNII
  • InChI=1S/C7H5NO2/c9-4-6-2-1-3-7(5-10)8-6/h1-5H
    Key: PMWXGSWIOOVHEQ-UHFFFAOYSA-N
  • C1=CC(=NC(=C1)C=O)C=O
Properties
Appearance white solid
Melting point 124 °C (255 °F; 397 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,6-Diformylpyridine is an organic compound with the formula C5H3N(CHO)2, and typically appears as a solid powder at room temperature. The molecule features formyl groups adjacent to the nitrogen of pyridine. The compound is prepared by oxidation of 2,6-dimethylpyridine.[1]

It condenses with amines to give diiminopyridine ligands,[2] as was demonstrated in Fraser Stoddart's synthesis of molecular Borromean rings.[3][4][5] It also finds use in the preparation of metal-coordinated polymer materials.[6] [7]

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References

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  1. ^ Forni, Lucio; Casalone, Gianluigi (1987). "Vapour Phase Oxidation of 2,6-Lutidine to 2,6-Pyridinedicarboxaldehyde. III: Kinetic Study". Applied Catalysis. 34: 317–328. doi:10.1016/S0166-9834(00)82465-3.
  2. ^ Britovsek, George J. P.; Bruce, Michael; Gibson, Vernon C.; Kimberley, Brian S.; Maddox, Peter J.; Mastroianni, Sergio; McTavish, Stuart J.; Redshaw, Carl; Solan, Gregory A.; Strömberg, Staffan; White, Andrew J. P.; Williams, David J. (1999). "Iron and Cobalt Ethylene Polymerization Catalysts Bearing 2,6-Bis(Imino)Pyridyl Ligands: Synthesis, Structures, and Polymerization Studies". Journal of the American Chemical Society. 121 (38): 8728–8740. doi:10.1021/ja990449w.
  3. ^ Chichak, K. S.; Cantrill, S. J.; Pease, A. R.; Chiu, S.-H.; Cave, G. W. V.; Atwood, J. L.; Stoddart, J. F. (2004). "Molecular Borromean Rings" (PDF). Science. 304 (5675): 1308–1312. Bibcode:2004Sci...304.1308C. doi:10.1126/science.1096914. PMID 15166376. S2CID 45191675.
  4. ^ Peters, Andrea J.; Chichak, Kelly S.; Cantrill, Stuart J.; Stoddart, J. Fraser (2005). "Nanoscale Borromean links for real". Chemical Communications (27): 3394–6. doi:10.1039/B505730B. PMID 15997275.
  5. ^ Yaghi, Omar M.; Kalmutzki, Markus J.; Diercks, Christian S. (2019). "Historical Perspective on the Discovery of Covalent Organic Frameworks". Introduction to Reticular Chemistry: Metal-Organic Frameworks and Covalent Organic Frameworks. Wiley-VCH. p. 188. ISBN 9783527821082.
  6. ^ Schoustra, Sybren K.; Smulders, Maarten M. J. (2023). "Metal Coordination in Polyimine Covalent Adaptable Networks for Tunable Material Properties and Enhanced Creep Resistance". Macromolecular Rapid Communications. 44 (5): 2200790. doi:10.1002/marc.202200790. PMID 36629864. S2CID 255593988.
  7. ^ Nasr, G.; Macron, T.; Gilles, A.; Mouline, Z.; Barboiu, M. (2012). "Metallodynameric membranes – toward the constitutional transport of gases". Chemical Communications. 48 (54): 6827–6829. doi:10.1039/C2CC32656F. PMID 22652555.
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