1,2-Cyclohexanedione

1,2-Cyclohexanedione
Names
	Preferred IUPAC name Cyclohexane-1,2-dione
Identifiers
CAS Number	765-87-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	12465;
ECHA InfoCard	100.011.050
PubChem CID	13006;
UNII	75C1OVW0FJ ;
CompTox Dashboard (EPA)	DTXSID6061101 ;
	InChI InChI=1S/C6H8O2/c7-5-3-1-2-4-6(5)8/h1-4H2 Key: OILAIQUEIWYQPH-UHFFFAOYSA-N;
	SMILES C1CCC(=O)C(=O)C1;
Properties
Chemical formula	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

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]

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

References

^ Hach, Clifford C.; Banks, Charles V.; Diehl, Harvey (1952). "1,2-Cyclohexanedione Dioxime". Org. Synth. 32: 35. doi:10.15227/orgsyn.032.0035.
^ 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.

[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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