1,3-Cyclohexanedione

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1,3-Cyclohexanedione
1,3-CHD.png
Names
Preferred IUPAC name
Cyclohexane-1,3-dione
Other names
CHD, dihydroresorcinol
Identifiers
3D model (JSmol)
385888
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.255 Edit this at Wikidata
EC Number
  • 207-980-0
200899
KEGG
UNII
  • InChI=1S/C6H8O2/c7-5-2-1-3-6(8)4-5/h1-4H2
    Key: HJSLFCCWAKVHIW-UHFFFAOYSA-N
  • C1CC(=O)CC(=O)C1
Properties
C6H8O2
Molar mass 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)
Acidity (pKa) 5.20 (H2O)[1]
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H318, H412
P264, P270, P273, P280, P301+P312, P305+P351+P338, P310, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[2]

Synthesis, structure, and reactivity[edit]

1,3-Cyclohexanedione is produced by semi-hydrogenation of resorcinol:[3][4]

C6H4(OH)2 + H2 → C6H8O2

1,3-Cyclohexanedione exists in solution predominantly as the enol tautomer.

Enolization of 1,3-cyclohexanedione.

It reacts under acid catalysis with alcohols to 3-alkoxyenones.[2] 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.[4]

Derivatives[edit]

Dimedone (5,5-dimethyl-1,3-cyclohexanedione) is a well established reagent.[5]

Several herbicides against grasses are formal derivatives of 1,3-cyclohexanedione. Examples of commercial products include cycloxydim, clethodim, tralkoxydim, butroxydim, profoxydim, and mesotrione.[6]

References[edit]

  1. ^ Terasawa, Tadao; Okada, Toshihiko (1977). "Novel heterocyclic synthons. Synthesis and properties of thia- and oxacyclohexane-3,5-diones". J. Org. Chem. 42 (7): 1163–1169. doi:10.1021/jo00427a014.
  2. ^ a b Guppi, Sanjeeva Rao; O'Doherty, George A. (2008). "1,3-Cyclohexadiene". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00921. ISBN 978-0471936237.
  3. ^ Thompson, R. B. (1947). "Dihydroresorcinol". Org. Synth. 27: 21. doi:10.15227/orgsyn.027.0021.
  4. ^ a b 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.
  5. ^ Strittmatter, Harald; Hildbrand, Stefan; Pollak, Peter (2007). "Malonic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a16_063.pub2. ISBN 978-3527306732.
  6. ^ Keith G. Watson (2011). "Cyclohexane-1,3-dione Oxime Ether Grass-Specific Herbicides and the Discovery of Butroxydim". Aust. J. Chem. 64 (4): 367–372. doi:10.1071/CH10366.