1,3-Cyclohexanedione

1,3-CHD.png 138 px skin-invert Cyclohexane-1,3-dione CHD, dihydroresorcinol 504-02-9 10434 10004 207-980-0 6UK3D2BXJT 17766 363919 C01066 385888 200899 1S/C6H8O2/c7-5-2-1-3-6(8)4-5/h1-4H2 HJSLFCCWAKVHIW-UHFFFAOYSA-N C1CC(=O)CC(=O)C1 6 8 2 Colorless or white solid 1.0861 g/cm3 105.5 5.20 (H2O) Terasawa Tadao Okada Toshihiko 1977 Novel heterocyclic synthons. Synthesis and properties of thia- and oxacyclohexane-3,5-diones 10.1021/jo00427a014 J. Org. Chem. 42 7 1163–1169 05 07 Danger 302 318 412 264 270 273 280 301+312 305+351+338 310 330 501 1,3-Cyclohexanedione is an organic compound with the formula (CH2)4(CO)2. It is one of three isomeric cyclohexanediones. It is a colorless compound that occurs naturally. It is the substrate for cyclohexanedione hydrolase. The compound exists mainly as the enol tautomer.1,3-Cyclohexadiene Sanjeeva Rao Guppi George A. O'Doherty 2008 10.1002/047084289X.rn00921 E-EROS Encyclopedia of Reagents for Organic Synthesis 978-0471936237 Synthesis, structure, and reactivity 1,3-Cyclohexanedione is produced by semi-hydrogenation of resorcinol:Dihydroresorcinol R. B. Thompson Org. Synth. 1947 27 21 10.15227/orgsyn.027.0021 free C6H4(OH)2 + H2 → C6H8O2 1,3-Cyclohexanedione exists in solution predominantly as the enol tautomer. left|thumb|Enolization of 1,3-cyclohexanedione. It reacts under acid catalysis with alcohols to 3-alkoxyenones. Its pKa is 5.26. Treatment of the sodium salt of the enolate with methyl iodide gives 2-methyl-1,3-cyclohexanedione, which also exists predominantly as the enol.Methyl-1,3-Cyclohexanedione A. B. Mekler S. Ramachandran S. Swaminathan Melvin S. Newman Org. Synth. 1961 41 56 10.15227/orgsyn.041.0056 free Derivatives Dimedone (5,5-dimethyl-1,3-cyclohexanedione) is a well established reagent.10.1002/14356007.a16_063.pub2 Malonic Acid and Derivatives Ullmann's Encyclopedia of Industrial Chemistry 2007 Strittmatter Harald Hildbrand Stefan Pollak Peter 978-3527306732 Several herbicides against grasses are formal derivatives of 1,3-cyclohexanedione. Examples of commercial products include cycloxydim, clethodim, tralkoxydim, butroxydim, sethoxydim, profoxydim, and mesotrione.Cyclohexane-1,3-dione Oxime Ether Grass-Specific Herbicides and the Discovery of Butroxydim Keith G. Watson Aust. J. Chem. 2011 64 4 367–372 10.1071/CH10366 1,3-Cyclohexanedione is also used in the manufacture of Ondansetron. References Category:Diketones