Dimedone
| Dimedone | |
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5,5-Dimethylcyclohexane-1,3-dione |
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Other names
Cyclomethone, |
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| Identifiers | |
| CAS number | 126-81-8  |
| PubChem | 31358 |
| ChemSpider | 29091 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C8H12O2 |
| Molar mass | 140.17968 |
| Appearance | Yellow crystals |
| Melting point |
147–150 °C (decomposes) |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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 colourimetry, crystallography, luminescence and spectrophotometric analysis. It can also be used for chemistry involving organic compounds of low electrical resistance.
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[edit] Synthesis
Dimedone is prepared from mesityl oxide and diethyl malonate[1].
[edit] Physical properties
Dimedone usually comes in the form of yellow 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).
[edit] 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]:
[edit] References
- ^ R. L. Shriner and H. R. Todd (1935). "5,5-dimethyl-1,3-cyclohexanedione". Organic Syntheses 15: 16. http://www.orgsyn.org/orgsyn/prep.asp?prep=cv2p0200.
- ^ Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (1st ed.). Oxford University Press. pp. p. 532. ISBN 978-0-19-850346-0.
- ^ M. Bolte and M. Scholtyssik (October 1997). "Dimedone at 133K". Acta Cryst. C53 (10): IUC9700013. doi:10.1107/S0108270197099423.
