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Revision as of 18:51, 12 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: {{cascite}} StdInChI StdInChIKey.← Previous edit Latest revision as of 03:57, 23 October 2024 edit undoCitation bot (talk | contribs)Bots5,424,581 edits Added bibcode. | Use this bot. Report bugs. | Suggested by Dominic3203 | Category:Diketones | #UCB_Category 71/206 
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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 351375247 | 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 = 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
| InChIKey = BADXJIPKFRBFOT-UHFFFAOYAX | InChIKey = BADXJIPKFRBFOT-UHFFFAOYAX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3 | StdInChI = 1S/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| 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}}


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