Dimedone

Dimedone
Names
	Preferred 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 ;
3D model (JSmol)	Interactive image;
ChemSpider	29091 ;
PubChem CID	31358;
UNII	B2B5DSX2FC ;
	InChI InChI=1S/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3 Key: BADXJIPKFRBFOT-UHFFFAOYSA-N ; 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). verify (what is ?) 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[edit]

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

Physical properties[edit]

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).

Chemical properties[edit]

Tautomerism[edit]

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]

Reaction with aldehydes[edit]

Dimedone reacts with aldehydes to give crystalline derivatives, whose melting points can be used to distinguish between aldehydes.^[4]

References[edit]

^ R. L. Shriner and H. R. Todd (1935). "5,5-dimethyl-1,3-cyclohexanedione". Organic Syntheses. 15: 16. doi:10.1002/0471264180.os015.06. ISBN 0471264229.
^ Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (1st ed.). Oxford University Press. p. 530. 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.
^ Horning, E. C.; Horning, M. G. (1946). "METHONE DERIVATIVES OF ALDEHYDES". The Journal of Organic Chemistry. 11 (1): 95–99. doi:10.1021/jo01171a014. ISSN 0022-3263.

[1] R. L. Shriner and H. R. Todd (1935). "5,5-dimethyl-1,3-cyclohexanedione". Organic Syntheses. 15: 16. doi:10.1002/0471264180.os015.06. ISBN 0471264229.

[2] Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (1st ed.). Oxford University Press. p. 530. ISBN 978-0-19-850346-0.

[3] M. Bolte and M. Scholtyssik (October 1997). "Dimedone at 133K". Acta Crystallogr. C. 53 (10): IUC9700013. doi:10.1107/S0108270197099423.

[4] Horning, E. C.; Horning, M. G. (1946). "METHONE DERIVATIVES OF ALDEHYDES". The Journal of Organic Chemistry. 11 (1): 95–99. doi:10.1021/jo01171a014. ISSN 0022-3263.

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