1,3-Cyclohexanedione
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| Names | |
|---|---|
Preferred IUPAC name Cyclohexane-1,3-dione | |
| Other names CHD, dihydroresorcinol | |
| Identifiers | |
CAS Number |
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3D model (JSmol) |
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Beilstein Reference | 385888 |
ChEBI |
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ChEMBL |
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ChemSpider |
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ECHA InfoCard | 100.007.255 |
EC Number | 207-980-0 |
Gmelin Reference | 200899 |
KEGG |
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PubChem CID |
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UNII |
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InChI
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SMILES
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| Properties | |
Chemical formula | C6H8O2 |
Molar mass | 7002112128000000000♠112.128 g·mol−1 |
| Appearance | Colorless or white solid |
Density | 1.0861 g/cm3 |
Melting point | 105.5 °C (221.9 °F; 378.6 K) |
| Hazards | |
GHS pictograms |   |
GHS signal word | Danger |
GHS hazard statements | H302, H318, H412 |
GHS precautionary statements | P264, P270, P273, P280, P301+312, P305+351+338, P310, P330, P501 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
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]
Synthesis, structure, and reactivity
1,3-Cyclohexanedione is produced by semi-hydrogenation of resorcinol:[2]
- C6H4(OH)2 + H2 → C6H8O2
1,3-Cyclohexanedione exists in solution as the enol. It reacts under acid catalysis with alcohols to 3-alkoxyenones.[1]
Enolization of 1,3-cyclohexanedione.
Its pKa is 5.26. Treatment of the sodium salt of the enolate with methyl iodide gives 2-methyl-1,3-cyclohexanedione, which despite the name, also exists predominantly as the enol.[2]
Derivatives
Dimedone, 5,5-dimethyl-1,3-cyclohexanedione is a well established reagent.
Several herbicides are formal derivatives of 1,3-cyclohexanedione. Examples of commercial products include Cycloxydim, Clethodim, Tralkoxydim, butroxydim, Profoxydim, and Quizalofop-P-ethyl.[3]
References
^ ab Guppi, Sanjeeva Rao; O'Doherty, George A. (2008). "1,3-Cyclohexadiene". e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00921..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output .citation q{quotes:"""""""'""'"}.mw-parser-output .citation .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-maint{display:none;color:#33aa33;margin-left:0.3em}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}
^ ab Mekler, A. B.; Ramachandran, S.; Swaminathan, S.; Newman, Melvin S. (1961). "Methyl-1,3-Cyclohexanedione". Org. Synth. 41: 56. doi:10.15227/orgsyn.041.0056.
^ Keith G. Watson (2011). "Cyclohexane-1,3-dione Oxime Ether Grass-Specific Herbicides and the Discovery of Butroxydim". Aust. J. Chem. 64: 367–372. doi:10.1071/CH10366.
