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Names | |||
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Preferred IUPAC name
5,5-Dimethylcyclohexane-1,3-dione | |||
Other names
Cyclomethone,
5,5-dimethyl-1,3-cyclohexanedione, Dimethyldihydroresorcinol, Methone | |||
Identifiers | |||
3D model (JSmol)
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ChemSpider | |||
ECHA InfoCard | 100.004.369 | ||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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Properties | |||
C8H12O2 | |||
Molar mass | 140.182 g·mol−1 | ||
Appearance | White solid | ||
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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Dimedone is an organic compound with the formula (CH3)2C(CH2)2(CO)2(CH2). Classified as a cyclic diketone, it is a derivative of 1,3-cyclohexanedione. It is a white solid that is soluble in water, as well as ethanol and methanol. It once was used as a reagent to test for the aldehyde functional group.
Dimedone is prepared from mesityl oxide and diethyl malonate via a Michael addition reaction.[1][2]
Dimedone is in equilibrium with its tautomer in solution — in a 2:1 keto to enol ratio in chloroform.[3]
Crystalline dimedone contains chains of molecules, in the enol form, linked by hydrogen bonds:[4]
Dimedone reacts with aldehydes to give crystalline derivatives, whose melting points can be used to distinguish between aldehydes.[5]