Dimedone

Dimedone

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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 3D model	Interactive image
PubChem	31358
InChI 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)
Vapor pressure	{{{value}}}
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.

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.

Diagram of tautomeric equilibrium of dimedone

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

Ball-and-stick model of a hydrogen-bonded dimedone chain, as found in the crystal structure