247:
154:
737:
24:
416:
697:
678:
33:
573:
858:
424:
396:
746:
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
490:
586:
921:
Yoshiro Ogata; Masaru
Tsuchida; Akihiko Muramoto (2006). "Controlled Synthesis of 2-Acetyl-6-carbethioxypyridine and 2-6-Diacetylpyridine from 2,6-Dimethylpyridine".
286:
486:
826:
Schmidt, R.; Welch, M.B.; Palackal, S.J.; Alt, H.G. (2001). "Hydrogenized iron(II) complexes as highly active ethene polymerization catalysts".
872:
Darmon, Jonathan M.; Turner, Zoë R.; Lobkovsky, Emil; Chirik, Paul J.; Finkelstein, K. D.; Wieghardt, K.; Debeer, S.; Chirik, P. J. (2012).
261:
736:
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111:
460:
204:
225:
514:
415:
972:
727:. Diiminopyridine ligands have been the focus of much interest due to their ability to traverse a wide range of
161:
856:, Agnese, G. & Burshchi, E., "Two Stage Process for Preparing 2,6-pyridinedicarboxylic acid"
506:
696:
502:
23:
688:
677:
494:
376:
81 °C (178 °F; 354 K) Sublimes at 110 to 130 °C (230 to 266 °F; 383 to 403 K)
149:
661:
641:
438:
408:
874:"Electronic Effects in 4-Substituted Bis(imino)pyridines and the Corresponding Reduced Iron Compounds"
853:
764:
728:
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45:
242:
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Diacetylpyridine is a popular starting material for ligands in coordination chemistry, often via
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The synthesis of 2,6-diacetylpyridine begins with oxidation of the methyl groups in
522:
653:
470:
668:. The diketone can be formed from the diester of picolinic acid groups through a
632:. It is a white solid that is soluble in organic solvents. It is a disubstituted
193:
799:
720:
452:
510:
935:
340:
122:
448:
907:
633:
549:
672:. The resulting adduct can be decarboxylated to give diacetylpyridine.
724:
361:
180:
162:
889:
444:
32:
637:
563:
Except where otherwise noted, data are given for materials in their
719:(DIP) class of ligands can be formed from diacetylpyridine through
110:
100:
518:
786:
Curtis, N. F. (2012). "The Advent of
Macrocyclic Chemistry".
735:
695:
676:
230:
270:
InChI=1S/C9H9NO2/c1-6(11)8-4-3-5-9(10-8)7(2)12/h3-5H,1-2H3
581:
755:
have been synthesized by varying the polyamine chain.
691:
provides an alternative synthesis for the diketone.
192:
781:
779:
660:. This process has been well established with
86:
8:
828:Journal of Molecular Catalysis A: Chemical
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152:
130:
15:
897:
687:Treating 2,6-pyridinedicarbonitrile with
212:
775:
291:
266:
241:
50:1,1′-(Pyridine-2,6-diyl)di(ethan-1-one)
386:126 °C (259 °F; 399 K)
143:
821:
819:
817:
273:Key: BEZVGIHGZPLGBL-UHFFFAOYSA-N
7:
183:
59:1,1′-(Pyridine-2,6-diyl)diethanone
14:
707:Precursor to Schiff base ligands
571:
414:
327:
321:
61:1-(6-Acetylpyridin-2-yl)ethanone
31:
22:
567:(at 25 °C , 100 kPa).
723:condensation with substituted
330:
315:
1:
840:10.1016/S1381-1169(01)00333-8
800:10.1080/10610278.2012.688123
989:
936:10.1080/00397910500186995
740:diiminopyridine_synthesis
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56:
44:
39:
30:
21:
788:Supramolecular Chemistry
636:. It is a precursor to
461:Precautionary statements
689:methylmagnesium bromide
751:. Similar penta- and
741:
701:
700:DAP synthesis Grignard
682:
662:potassium permanganate
642:coordination chemistry
294:CC(=O)c1cccc(n1)C(=O)C
854:CA patent 1108617
739:
699:
681:DAP synthesis Claisen
680:
65:2,6-Bisacetylpyridine
17:2,6-Diacetylpyridine
765:2,6-Diformylpyridine
749:tetradentate ligands
670:Claisen condensation
606:2,6-Diacetylpyridine
46:Preferred IUPAC name
753:hexadentate ligands
348: g·mol
18:
742:
713:template reactions
702:
683:
594:Infobox references
542:Related compounds
16:
930:(17): 2317–2324.
890:10.1021/om201212m
602:Chemical compound
600:
599:
530:Safety data sheet
439:Hazard statements
226:CompTox Dashboard
112:Interactive image
980:
973:Acetyl compounds
948:
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911:
901:
884:(6): 2275–2285.
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850:
844:
843:
834:(1–2): 155–173.
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812:
811:
783:
729:oxidation states
666:selenium dioxide
658:dipicolinic acid
610:organic compound
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578:
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556:2-acetylpyridine
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310:Chemical formula
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878:Organometallics
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717:diiminopyridine
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589: ?)
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356:White crystals
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924:Synth. Commun.
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794:(7): 439–447.
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565:standard state
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491:P305+P351+P338
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144:ECHA InfoCard
141:
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25:
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791:
787:
745:
710:
686:
654:2,6-lutidine
651:
605:
604:
430:
397:
71:Identifiers
57:Other names
721:Schiff base
425:Signal word
366:1.119 g/cm
353:Appearance
303:Properties
150:100.013.130
957:Categories
771:References
536:MSDS sheet
409:Pictograms
341:Molar mass
214:P34UXL3MYV
123:ChemSpider
99:3D model (
78:CAS Number
963:Pyridines
648:Synthesis
612:with the
550:pyridines
515:P403+P233
507:P337+P313
503:P332+P313
487:P304+P340
483:P302+P352
400:labelling
171:214-442-9
163:EC Number
88:1129-30-2
944:93168188
908:22675236
808:96660708
759:See also
725:anilines
656:to form
634:pyridine
624:N(C(O)CH
548:Related
391:Hazards
968:Ligands
899:3366276
715:. The
638:ligands
614:formula
587:what is
585: (
431:Warning
362:Density
346:163.176
181:PubChem
942:
906:
896:
860:
806:
608:is an
582:verify
579:
532:(SDS)
287:SMILES
40:Names
940:S2CID
804:S2CID
262:InChI
194:70790
132:63955
101:JSmol
904:PMID
664:and
523:P501
519:P405
511:P362
499:P321
495:P312
479:P280
475:P271
471:P264
467:P261
453:H335
449:H319
445:H315
205:UNII
63:DAP
932:doi
894:PMC
886:doi
836:doi
832:179
796:doi
640:in
398:GHS
231:EPA
184:CID
959::
938:.
928:35
902:.
892:.
882:31
880:.
876:.
830:.
816:^
802:.
792:24
790:.
778:^
731:.
644:.
521:,
517:,
513:,
509:,
505:,
501:,
497:,
493:,
489:,
485:,
481:,
477:,
473:,
469:,
451:,
447:,
402::
946:.
934::
910:.
888::
842:.
838::
810:.
798::
630:2
628:)
626:3
622:3
620:H
618:5
616:C
577:Y
334:2
331:O
328:N
325:9
322:H
319:9
316:C
233:)
229:(
103:)
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