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Dimedone

From Wikipedia, the free encyclopedia
Dimedone
Names
Preferred IUPAC name
5,5-Dimethylcyclohexane-1,3-dione
Other names
Cyclomethone,
5,5-dimethyl-1,3-cyclohexanedione,
Dimethyldihydroresorcinol,
Methone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.369 Edit this at Wikidata
UNII
  • InChI=1S/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3 checkY
    Key: BADXJIPKFRBFOT-UHFFFAOYSA-N checkY
  • InChI=1/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3
    Key: BADXJIPKFRBFOT-UHFFFAOYAX
  • O=C1CC(=O)CC(C)(C)C1
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).
checkY verify (what is checkYX markN ?)

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. Derivatives of dimedone and 1,3-cyclohexanedione derivatives are used as reagents for selective detection of sulfenic acids in biological samples.[1]

Synthesis

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Dimedone is prepared from mesityl oxide and diethyl malonate via a Michael addition reaction.[2][3]

Chemical properties

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Tautomerism

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Dimedone is in equilibrium with its tautomer in solution — in a 2:1 keto to enol ratio in chloroform.[4]

Diagram of tautomeric equilibrium of dimedone

Crystalline dimedone contains chains of molecules, in the enol form, linked by hydrogen bonds:[5]

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

Reaction with aldehydes

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Dimedone reacts with aldehydes to give crystalline derivatives, whose melting points can be used to distinguish between aldehydes.[6]

Reaction of dimedone with formaldehyde

References

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  1. ↑ Klomsiri, Chananat; Nelson, Kimberly J.; Bechtold, Erika; Soito, Laura; Johnson, Lynnette C.; Lowther, W. Todd; Ryu, Seong-Eon; King, S. Bruce; Furdui, Cristina M.; Poole, Leslie B. (2010). "Use of dimedone-based chemical probes for sulfenic acid detection evaluation of conditions affecting probe incorporation into redox-sensitive proteins". Methods in Enzymology. 473: 77–94. doi:10.1016/S0076-6879(10)73003-2. ISSN 1557-7988. PMC 3795394. PMID 20513472.
  2. ↑ R. L. Shriner and H. R. Todd (1935). "5,5-dimethyl-1,3-cyclohexanedione". Organic Syntheses. 15: 14. doi:10.15227/orgsyn.015.0014.
  3. ↑ "Dimedone synthesis". ChemTube3D. Retrieved 11 May 2023.
  4. ↑ Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (1st ed.). Oxford University Press. p. 530. ISBN 978-0-19-850346-0.
  5. ↑ M. Bolte and M. Scholtyssik (October 1997). "Dimedone at 133K". Acta Crystallogr. C. 53 (10): IUC9700013. Bibcode:1997AcCrC..53C0013B. doi:10.1107/S0108270197099423.
  6. ↑ 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. PMID 21013441.
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