Dimedone

Names

IUPAC name

5,5-Dimethylcyclohexane-1,3-dione

Other names

Cyclomethone,
5,5-dimethyl-1,3-cyclohexanedione,
Dimethyldihydroresorcinol,
Methone

Identifiers

CAS Number

126-81-8^Y

ChemSpider

29091^Y

Jmol interactive 3D

InChI=1S/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3^Y
Key: BADXJIPKFRBFOT-UHFFFAOYSA-N^Y
InChI=1/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3
Key: BADXJIPKFRBFOT-UHFFFAOYAX

SMILES

O=C1CC(=O)CC(C)(C)C1

Properties

Chemical formula

C₈H₁₂O₂

Molar mass

140.17968

Appearance

Yellow crystals

Melting point

147 to 150 °C (297 to 302 °F; 420 to 423 K) (decomposes)

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

Dimedone is a cyclic diketone used in organic chemistry to determine whether a compound contains an aldehyde group. Cyclohexanediones in general can be used as catalysts in the formation of transition-metal complexes. Other uses include applications in colorimetry, crystallography, luminescence and spectrophotometric analysis. It can also be used for chemistry involving organic compounds of low electrical resistance.

Synthesis

Dimedone is prepared from mesityl oxide and diethyl malonate.^[1]

Physical properties

Dimedone usually comes in the form of white crystals. It is stable under ambient conditions and soluble in water, as well as ethanol and methanol. It has a melting point range of 147–150 °C (420–423 K).

Tautomerism

Dimedone is in equilibrium with its tautomer in solution — in a 2:1 keto to enol ratio in chloroform.^[2]

Crystalline dimedone contains chains of molecules, in the enol form, linked by hydrogen bonds:^[3]

References

↑ R. L. Shriner and H. R. Todd (1935). "5,5-dimethyl-1,3-cyclohexanedione". Organic Syntheses 15: 16. doi:10.1002/0471264180.os015.06.
↑ Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (1st ed.). Oxford University Press. p. 532. ISBN 978-0-19-850346-0.
↑ M. Bolte and M. Scholtyssik (October 1997). "Dimedone at 133K". Acta Crystallogr. C 53 (10): IUC9700013. doi:10.1107/S0108270197099423.

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