1,2-Cyclohexanedione

1,2-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 is soluble in a variety of organic solvents. It can be prepared by oxidation of cyclohexanone by selenium dioxide.[1] The enol is about 1 kcal/mol more stable than the diketo form.[2]

1,2-Cyclohexanedione
Names
Preferred IUPAC name
Cyclohexane-1,2-dione
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.050
UNII
  • InChI=1S/C6H8O2/c7-5-3-1-2-4-6(5)8/h1-4H2
    Key: OILAIQUEIWYQPH-UHFFFAOYSA-N
  • C1CCC(=O)C(=O)C1
Properties
C6H8O2
Molar mass 112.128 g·mol−1
Appearance white, waxy solid
Density 1.1305 g/cm3
Melting point 40 °C
Boiling point 194 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Numerous diimine and dioxime ligands have been prepared from this diketone. It condenses with 1,2-diamines to give diaza heterocycles.

References
  1. Hach, Clifford C.; Banks, Charles V.; Diehl, Harvey (1952). "1,2-Cyclohexanedione Dioxime". Org. Synth. 32: 35. doi:10.15227/orgsyn.032.0035.
  2. Jana, Kalyanashis; Ganguly, Bishwajit (2018). "DFT Study to Explore the Importance of Ring Size and Effect of Solvents on the Keto–Enol Tautomerization Process of α- and β-Cyclodiones". ACS Omega. 3 (7): 8429–8439. doi:10.1021/acsomega.8b01008. PMC 6644555. PMID 31458971.
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