2,6-Diacetylpyridine

changed 444216370 2,6-Diacetylpyridine 2,6-Diacetylpyridine.svg 180 Skeletal formula 2,6-Ac2py.jpg 230 1,1′-(Pyridine-2,6-diyl)di(ethan-1-one) 1,1′-(Pyridine-2,6-diyl)diethanone1-(6-Acetylpyridin-2-yl)ethanoneDAP 2,6-Bisacetylpyridine CC(=O)c1cccc(n1)C(=O)C correct chemspider 63955 InChI=1S/C9H9NO2/c1-6(11)8-4-3-5-9(10-8)7(2)12/h3-5H,1-2H3 correct chemspider BEZVGIHGZPLGBL-UHFFFAOYSA-N correct CAS 1129-30-2 correct FDA P34UXL3MYV 70790 214-442-9 9 9 1 2 White crystals 1.119 g/cm3 81 Sublimes at 110 to 130 C F K 126 MSDS sheet 07 Warning 315 319 335 261 264 271 280 302+352 304+340 305+351+338 312 321 332+313 337+313 362 403+233 405 501 pyridines 2-acetylpyridine 2,6-Diacetylpyridine is an organic compound with the formula C5H3N(C(O)CH3)2. It is a white solid that is soluble in organic solvents. It is a disubstituted pyridine. It is a precursor to ligands in coordination chemistry. The Advent of Macrocyclic Chemistry Curtis, N. F. Supramolecular Chemistry 24 7 439–447 2012 10.1080/10610278.2012.688123 96660708 Synthesis The synthesis of 2,6-diacetylpyridine begins with oxidation of the methyl groups in 2,6-lutidine to form dipicolinic acid. This process has been well established with potassium permanganate and selenium dioxide. CA 1108617 patent Two Stage Process for Preparing 2,6-pyridinedicarboxylic acid Agnese, G. Ghelli, G. Burshchi, E. The diketone can be formed from the diester of picolinic acid groups through a Claisen condensation. 10.1021/om201212m 22675236 3366276 Electronic Effects in 4-Substituted Bis(imino)pyridines and the Corresponding Reduced Iron Compounds Organometallics 31 6 2275–2285 2012 Darmon Jonathan M. Turner Zoë R. Lobkovsky Emil Chirik Paul J. Finkelstein K. D. Wieghardt K. Debeer S. Chirik P. J. The resulting adduct can be decarboxylated to give diacetylpyridine. Controlled Synthesis of 2-Acetyl-6-carbethioxypyridine and 2-6-Diacetylpyridine from 2,6-Dimethylpyridine Yoshiro Ogata Masaru Tsuchida Akihiko Muramoto Synth. Commun. 35 17 2317–2324 2006 10.1080/00397910500186995 93168188 center|650px|DAP synthesis Claisen Treating 2,6-pyridinedicarbonitrile with methylmagnesium bromide provides an alternative synthesis for the diketone. Hydrogenized iron(II) complexes as highly active ethene polymerization catalysts Schmidt, R. Welch, M.B. Palackal, S.J. Alt, H.G. Journal of Molecular Catalysis A: Chemical 179 1–2 155–173 2001 10.1016/S1381-1169(01)00333-8 325px|center|DAP synthesis Grignard Precursor to Schiff base ligands Diacetylpyridine is a popular starting material for ligands in coordination chemistry, often via template reactions. The diiminopyridine (DIP) class of ligands can be formed from diacetylpyridine through Schiff base condensation with substituted anilines. Diiminopyridine ligands have been the focus of much interest due to their ability to traverse a wide range of oxidation states. 600px|center|diiminopyridine_synthesis In azamacrocycle chemistry, diacetylpyridines can undergo the same Schiff base condensation with N1-(3-aminopropyl)propane-1,3-diamines. The product of the condensation can be hydrogenated to yield macrocyclic tetradentate ligands. Similar penta- and hexadentate ligands have been synthesized by varying the polyamine chain. See also 2,6-Diformylpyridine References Category:Disubstituted pyridines Category:Ligands Category:Acetyl compounds