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1,4-Cyclohexanedione

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1,4-Cyclohexanedione
Chemical structure of Cyclohexanedione
Chemical structure of Cyclohexanedione
Names
Preferred IUPAC name Cyclohexane-1,4-dione
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 774152
ChEBI
ChemSpider
ECHA InfoCard 100.010.279 Edit this at Wikidata
EC Number
  • 211-306-0
Gmelin Reference 101292
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H8O2/c7-5-1-2-6(8)4-3-5/h1-4H2Key: DCZFGQYXRKMVFG-UHFFFAOYSA-N
  • InChI=1/C6H8O2/c7-5-1-2-6(8)4-3-5/h1-4H2Key: DCZFGQYXRKMVFG-UHFFFAOYAA
SMILES
  • C1CC(=O)CCC1=O
Properties
Chemical formula C6H8O2
Molar mass 112.128 g·mol
Appearance White solid
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 mmHg)
Solubility in water Very
Solubility Soluble in ethanol. Insoluble in diethyl ether.
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Preparation

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

This dione condenses with malononitrile to give an intermediate that can be dehydrogenated to tetracyanoquinodimethane (TCNQ).

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.
  3. 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.
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