1,3-Cyclohexanedione











































































































1,3-Cyclohexanedione

1,3-CHD.png
Names

Preferred IUPAC name
Cyclohexane-1,3-dione

Other names
CHD, dihydroresorcinol

Identifiers

CAS Number
  • 504-02-9

3D model (JSmol)
  • Interactive image

Beilstein Reference

 385888

ChEBI
  • CHEBI:17766

ChEMBL
  • ChEMBL363919

ChemSpider
  • 10004

ECHA InfoCard
100.007.255

EC Number
 207-980-0

Gmelin Reference

 200899

KEGG
  • C01066


PubChem CID
  • 10434

UNII
  • 6UK3D2BXJT




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
The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)

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




  1. ^ 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}


  2. ^ 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.


  3. ^ 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.








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