1,4-Cyclohexanedione

1,4-Cyclohexanedione is an organic compound with the formula (CH2)4(CO)2. This white solid is one of the three isomeric cyclohexanediones. This particular diketone is used as a building block in the synthesis of more complex molecules.

1,4-Cyclohexanedione[1]
Names
Preferred IUPAC name
Cyclohexane-1,4-dione
Identifiers
CAS Number
3D model (JSmol)
3DMet
Beilstein Reference
 774152
ChEBI
ChemSpider
ECHA InfoCard 100.010.279
EC Number
  • 211-306-0
Gmelin Reference
 101292
KEGG
PubChem CID
CompTox Dashboard (EPA)
Properties
Chemical formula
 C6H8O2
Molar mass 112.127 g/mol
Melting point 77 to 78.5 °C (170.6 to 173.3 °F; 350.1 to 351.6 K)
Boiling point 130 to 133 °C (266 to 271 °F; 403 to 406 K) (20 mm.)
Solubility in water
 Very
Solubility Soluble in ethanol. Insoluble in diethyl ether.
Hazards
GHS pictograms
GHS Signal word Warning
GHS hazard statements
 H315, H319, H335
GHS precautionary statements
 P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
Flash point 132 °C (270 °F; 405 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation

1,4-Cyclohexanedione is prepared in two steps from diesters of succinic acid. Specifically under basic conditions, the diethyl ester condenses to give the cyclohexenediol derivative diethylsuccinoylsuccinate. This intermediate can be hydrolysed and decarboxylated to afford the desired dione.[2]

References
  1. MSDS for 1,4-Cyclohexanedione
  2. Nielsen, Arnold T.; Carpenter, Wayne R. (1965). "1,4-Cyclohexanedione". Organic Syntheses. 45: 25. doi:10.15227/orgsyn.045.0025.
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