1,4-Cyclohexanedione

changed changed 477186325 MSDS for 1,4-Cyclohexanedione 1,4-Cyclohexanedione 1,4-Cyclohexanedione.png 80px Chemical structure of Cyclohexanedione skin-invert Cyclohexane-1,4-dione correct chemspider correct EBI 28286 11995 correct kegg C08063 1/C6H8O2/c7-5-1-2-6(8)4-3-5/h1-4H2 DCZFGQYXRKMVFG-UHFFFAOYAA correct chemspider 1S/C6H8O2/c7-5-1-2-6(8)4-3-5/h1-4H2 correct chemspider DCZFGQYXRKMVFG-UHFFFAOYSA-N correct CAS 637-88-7 correct FDA BJS27Z99AM C1CC(=O)CCC1=O 211-306-0 12511 101292 774152 B01109 6 8 2 White solid 77 to 78.5 130 to 133 (20 mmHg) Very Soluble in ethanol. Insoluble in diethyl ether. 132 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 1,4-Cyclohexanedione is an organic compound with the formula (CH2)4(CO)2. This white solid is one of the three isomeric cyclohexanediones. This particular diketone is used as a building block in the synthesis of more complex molecules. Preparation 1,4-Cyclohexanedione is prepared in two steps from diesters of succinic acid. Specifically under basic conditions, the diethyl succinate condenses to give the cyclohexenediol derivative diethylsuccinoylsuccinate. This intermediate can be hydrolysed and decarboxylated to afford the desired dione.10.15227/orgsyn.045.0025 free 1,4-Cyclohexanedione Organic Syntheses Arnold T. Nielsen Wayne R. Carpenter 45 25 1965 This dione condenses with malononitrile to give an intermediate that can be dehydrogenated to tetracyanoquinodimethane (TCNQ).10.1002/14356007.a16_063.pub2 Malonic Acid and Derivatives Ullmann's Encyclopedia of Industrial Chemistry 2007 Strittmatter Harald Hildbrand Stefan Pollak Peter 978-3-527-30673-2 Reactions and uses Protection of one of the carbonyl groups with ethylene glycol affords 1,4-cyclohexanedione monoethylene glycol ketal (1,4-dioxaspiro[4.5]decan-8-one).孙玉亮, et al. CN109503545 (2019 to Hebei caike New Material Technology Co., Ltd.).王淑梅, et al. CN111039917 (2020 to Tsaker Chemical Zhangzhou Co ltd). This compound is useful because it finds application in the synthesis of ramatroban, ciclindole, flucindole, LY-344864, frovatriptan, epibatidine,Hassner, A. Belostotskii, A. M. Tetrahedron Letters A simple method of preparation of 7-alkyl-7-azabicyclo[2.2.1]heptanes 36 10 1709–1712 March 1995 https://linkinghub.elsevier.com/retrieve/pii/004040399500051D 10.1016/0040-4039(95)00051-D subscription Davis, C. R. Johnson, R. A. Cialdella, J. I. Liggett, W. F. Mizsak, S. A. Marshall, V. P. The Journal of Organic Chemistry Microbiological Oxygenation of Bridgehead Azabicycloalkanes 62 7 2244–2251 1 April 1997 https://pubs.acs.org/doi/10.1021/jo962192f 10.1021/jo962192f subscription quinelorane,Doll, M. K.-H. Nichols, D. E. Kilts, J. D. Prioleau, C. Lawler, C. P. Lewis, M. M. Mailman, R. B. Journal of Medicinal Chemistry Synthesis and Dopaminergic Properties of Benzo-Fused Analogues of Quinpirole and Quinelorane 42 5 935–940 1 March 1999 https://pubs.acs.org/doi/10.1021/jm9804533 10.1021/jm9804533 subscription bromadol,Bernd Sundermann, Hagen-Heinrich Hennies, Werner Englberger, Stephan Wnendt, 7183436 (2007 to Gruenenthal Gmbh).Bernd Sundermann, Hagen-Heinrich Hennies, Werner Englberger, Babette-Yvonne Koegel, 7211694 (2007 to Gruenenthal Gmbh) and C-8813. References Category:Diketones Category:Cyclohexanes