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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 401995012 | verifiedrevid = 401997177
|ImageFileL1=dimedone.png | ImageFileL1 =dimedone.png
|ImageSizeL1=120px
|ImageFileR1=Dimedone-3D-balls.png | ImageFileR1 =Dimedone-3D-balls.png
⚫ | PIN =5,5-Dimethylcyclohexane-1,3-dione
|ImageSizeR1=120px
⚫ | OtherNames =Cyclomethone,<br>5,5-dimethyl-1,3-cyclohexanedione,<br>Dimethyldihydroresorcinol,<br>Methone
⚫ |IUPACName=5,5-Dimethylcyclohexane-1,3-dione
⚫ |Section1={{Chembox Identifiers
⚫ |OtherNames=Cyclomethone,<br>5,5-dimethyl-1,3-cyclohexanedione,<br>Dimethyldihydroresorcinol,<br>Methone
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ |Section1= {{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 29091 | ChemSpiderID = 29091
| InChI = 1/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3 | InChI = 1/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3
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| StdInChIKey = BADXJIPKFRBFOT-UHFFFAOYSA-N | StdInChIKey = BADXJIPKFRBFOT-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=126-81-8 | CASNo =126-81-8
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem=31358
| UNII = B2B5DSX2FC
⚫ | SMILES = O=C1CC(=O)CC(C)(C)C1
| PubChem =31358
⚫ | SMILES = O=C1CC(=O)CC(C)(C)C1
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=8|H=12|O=2
| Formula=C<sub>8</sub>H<sub>12</sub>O<sub>2</sub>
| MolarMass=140.17968 | MolarMass =
| Appearance=Yellow crystals | Appearance =White solid
| Density= | Density =
| MeltingPtC = 147 to 150
| MeltingPt=147-150 °C (decomposes)
| MeltingPt_notes = (decomposes)
| BoilingPt=
| BoilingPt =
| Solubility=
| Solubility =
⚫ }}
⚫ |Section3= {{Chembox Hazards
| MainHazards=
| FlashPt=
| Autoignition=
}} }}
⚫ |Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
⚫ }}
}} }}


'''Dimedone''' is an organic compound with the formula {{chem2|(CH3)2C(CH2)2(CO)2(CH2)}}. Classified as a cyclic ], it is a derivative of ]. It is a white solid that is soluble in water, as well as ] and ]. It once was used as a reagent to test for the ] ].
'''Dimedone''' is a cyclic ] used in ] to determine whether a compound contains an ] 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.


== Synthesis == == Synthesis ==
Dimedone is prepared from ] and ]<ref>{{ cite journal | journal = Organic Syntheses | volume = 15 | year = 1935 | pages = 16 | url = http://www.orgsyn.org/orgsyn/prep.asp?prep=cv2p0200 | title = 5,5-dimethyl-1,3-cyclohexanedione | author = R. L. Shriner and H. R. Todd}}</ref>. Dimedone is prepared from ] and ] via a ].<ref>{{ cite journal | journal = Organic Syntheses | volume = 15 | year = 1935 | pages = 16 | url = http://www.orgsyn.org/orgsyn/prep.asp?prep=cv2p0200 | title = 5,5-dimethyl-1,3-cyclohexanedione | author = R. L. Shriner and H. R. Todd | doi=10.1002/0471264180.os015.06| isbn = 0471264229 }}</ref><ref>{{cite web |title=Dimedone synthesis |url=https://www.chemtube3d.com/conjugate-addition-dimedone-synthesis/ |website=ChemTube3D |access-date=11 May 2023 |language=en}}</ref>


== Physical properties == == Chemical properties ==
Dimedone usually comes in the form of yellow crystals. It is stable under ambient conditions and soluble in water, as well as ] and ]. It has a melting point range of 147 - 150 °C (420 - 423 K).


== Tautomerism == === Tautomerism ===
Dimedone is in equilibrium with its ] in solution — in a 2:1 keto to enol ratio in ]<ref>{{Clayden|pages=p. 532}}</ref>. Dimedone is in equilibrium with its ] in solution — in a 2:1 keto to enol ratio in ].<ref>{{Clayden|pages=530}}</ref>


] ]


Crystalline dimedone contains chains of molecules, in the enol form, linked by ]s<ref>{{ cite journal | journal = Acta Cryst. | volume = C53 | issue = 10 | month = October | year = 1997 | pages = IUC9700013 | doi = 10.1107/S0108270197099423 | title = Dimedone at 133K | author = M. Bolte and M. Scholtyssik }}</ref>: Crystalline dimedone contains chains of molecules, in the enol form, linked by ]s:<ref>{{ cite journal | journal = Acta Crystallogr. C | volume = 53 | issue = 10 |date=October 1997 | pages = IUC9700013 | doi = 10.1107/S0108270197099423 | title = Dimedone at 133K | author = M. Bolte and M. Scholtyssik | doi-access = free | bibcode = 1997AcCrC..53C0013B }}</ref>


] ]

=== Reaction with aldehydes ===
Dimedone reacts with aldehydes to give crystalline derivatives, whose melting points can be used to distinguish between aldehydes.<ref>{{Cite journal |last1=Horning |first1=E. C. |last2=Horning |first2=M. G. |title=Methone Derivatives of Aldehydes |date=1946 |url=https://pubs.acs.org/doi/abs/10.1021/jo01171a014 |journal=The Journal of Organic Chemistry |language=en |volume=11 |issue=1 |pages=95–99 |doi=10.1021/jo01171a014 |pmid=21013441 |issn=0022-3263}}</ref>

:]


==References== ==References==
{{reflist}} {{reflist}}


] ]
]

]
]
]
]

Latest revision as of 03:57, 23 October 2024

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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.369 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3Key: BADXJIPKFRBFOT-UHFFFAOYSA-N
  • InChI=1/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3Key: BADXJIPKFRBFOT-UHFFFAOYAX
SMILES
  • O=C1CC(=O)CC(C)(C)C1
Properties
Chemical formula C8H12O2
Molar mass 140.182 g·mol
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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

Synthesis

Dimedone is prepared from mesityl oxide and diethyl malonate via a Michael addition reaction.

Chemical properties

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

Reaction with aldehydes

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

Reaction of dimedone with formaldehyde

References

  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. "Dimedone synthesis". ChemTube3D. Retrieved 11 May 2023.
  3. Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (1st ed.). Oxford University Press. p. 530. ISBN 978-0-19-850346-0.
  4. M. Bolte and M. Scholtyssik (October 1997). "Dimedone at 133K". Acta Crystallogr. C. 53 (10): IUC9700013. Bibcode:1997AcCrC..53C0013B. doi:10.1107/S0108270197099423.
  5. 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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