2,6-Diacetylpyridine

2,6-Diacetylpyridine
Names
	Preferred IUPAC name 1,1'-(Pyridine-2,6-diyl)di(ethan-1-one)
	Other names 1,1'-(Pyridine-2,6-diyl)diethanone; 1-(6-Acetylpyridin-2-yl)ethanone; DAP ; 2,6-Bisacetylpyridine
Identifiers
CAS Number	1129-30-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	63955 ;
ECHA InfoCard	100.013.130
EC Number	214-442-9;
PubChem CID	70790;
CompTox Dashboard (EPA)	DTXSID10150202 ;
	InChI InChI=1S/C9H9NO2/c1-6(11)8-4-3-5-9(10-8)7(2)12/h3-5H,1-2H3 Key: BEZVGIHGZPLGBL-UHFFFAOYSA-N ;
	SMILES CC(=O)c1cccc(n1)C(=O)C;
Properties
Chemical formula	C9H9NO2
Molar mass	163.176 g·mol−1
Appearance	White crystals
Density	1.119 g/cm³
Melting point	81 °C (178 °F; 354 K) Sublimes at 110 to 130 °C (230 to 266 °F; 383 to 403 K)
Boiling point	126 °C (259 °F; 399 K)
Hazards
Safety data sheet	MSDS sheet
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
Related compounds
Related pyridines	2-acetylpyridine
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

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.[1][2]

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.[3] The diketone can be formed from the diester of picolinic acid groups through a Claisen condensation.[4] The resulting adduct can be decarboxylated to give diacetylpyridine.[5]

DAP synthesis Claisen

Treating 2,6-pyridinedicarbonitrile with methylmagnesium bromide provides an alternative synthesis for the diketone.[2]

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.[2]

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.[1]

azamacrocycle_synthesis

gollark: Well, actually, I just used anomalous "beeoids" in Esobot to seed its RNG.

gollark: If you look at the code and then use anything vaguely related to any part of it in anything you right, it immediately becomes the property of the FSF.

gollark: Idea: design an even more restrictive license than AGPLv3.

gollark: How has nobody realized this?

gollark: Macron is literally just metahistomorphic semifunctors.

References

Curtis, N. F. (2012). "The Advent of Macrocyclic Chemistry". Supramolecular Chemistry. 24 (7): 439–447. doi:10.1080/10610278.2012.688123.
Schmidt, R.; Welch, M.B.; Palackal, S.J.; Alt, H.G. (2001). "Hydrogenized iron(II) complexes as highly active ethene polymerization catalysts". Journal of Molecular Catalysis A: Chemical. 179 (1–2): 155–173. doi:10.1016/S1381-1169(01)00333-8.
CA patent 1108617, Agnese, G. & Burshchi, E., "Two Stage Process for Preparing 2,6-pyridinedicarboxylic acid"
Darmon, Jonathan M.; Turner, Zoë R.; Lobkovsky, Emil; Chirik, Paul J.; Finkelstein, K. D.; Wieghardt, K.; Debeer, S.; Chirik, P. J. (2012). "Electronic Effects in 4-Substituted Bis(imino)pyridines and the Corresponding Reduced Iron Compounds". Organometallics. 31 (6): 2275–2285. doi:10.1021/om201212m. PMC 3366276. PMID 22675236.
Yoshiro Ogata; Masaru Tsuchida; Akihiko Muramoto (2006). "Controlled Synthesis of 2-Acetyl-6-carbethioxypyridine and 2-6-Diacetylpyridine from 2,6-Dimethylpyridine". Synth. Commun. 35 (17): 2317–2324. doi:10.1080/00397910500186995.

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[azamacrocycle-1] Curtis, N. F. (2012). "The Advent of Macrocyclic Chemistry". Supramolecular Chemistry. 24 (7): 439–447. doi:10.1080/10610278.2012.688123.

[DIP-2] Schmidt, R.; Welch, M.B.; Palackal, S.J.; Alt, H.G. (2001). "Hydrogenized iron(II) complexes as highly active ethene polymerization catalysts". Journal of Molecular Catalysis A: Chemical. 179 (1–2): 155–173. doi:10.1016/S1381-1169(01)00333-8.

[3] CA patent 1108617, Agnese, G. & Burshchi, E., "Two Stage Process for Preparing 2,6-pyridinedicarboxylic acid"

[4] Darmon, Jonathan M.; Turner, Zoë R.; Lobkovsky, Emil; Chirik, Paul J.; Finkelstein, K. D.; Wieghardt, K.; Debeer, S.; Chirik, P. J. (2012). "Electronic Effects in 4-Substituted Bis(imino)pyridines and the Corresponding Reduced Iron Compounds". Organometallics. 31 (6): 2275–2285. doi:10.1021/om201212m. PMC 3366276. PMID 22675236.

[5] Yoshiro Ogata; Masaru Tsuchida; Akihiko Muramoto (2006). "Controlled Synthesis of 2-Acetyl-6-carbethioxypyridine and 2-6-Diacetylpyridine from 2,6-Dimethylpyridine". Synth. Commun. 35 (17): 2317–2324. doi:10.1080/00397910500186995.