cyclopentanone
{{chembox
| Verifiedimages = changed
| Watchedfields = changed
| verifiedrevid = 443548992
| Reference=Merck Index, 11th Edition, 2748.
| Name = Cyclopentanone
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFileR1 = Cyclopentanone.png
| ImageSizeR1 = 80px
| ImageNameR1 = Cyclopentanone
| ImageFileL1 = Cyclopentanone-3D-balls-by-AHRLS-2012.png
| ImageSizeL1 = 80px
| ImageFile2 = AW Cyclopentanone.jpg
| PIN = Cyclopentanone
| OtherNames = Ketocyclopentane
Adipic ketone
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 220W81TN3S
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16486
| SMILES = C1CCC(=O)C1
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8141
| PubChem = 8452
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C00557
| InChI = 1/C5H8O/c6-5-3-1-2-4-5/h1-4H2
| InChIKey = BGTOWKSIORTVQH-UHFFFAOYAP
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 18620
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H8O/c6-5-3-1-2-4-5/h1-4H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BGTOWKSIORTVQH-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 120-92-3
| RTECS = GY4725000
}}
|Section2={{Chembox Properties
| Formula = C5H8O
| MolarMass = 84.12 g/mol
| Appearance = clear, colorless liquid
| Odor = peppermint-like
| Density = 0.95 g/cm3, liquid
| Solubility = Slightly soluble
| MeltingPtC = -58.2
| BoilingPtC = 130.6
| Viscosity =
| MagSus = −51.63·10−6 cm3/mol
}}
|Section7={{Chembox Hazards
| MainHazards =
| FlashPtC = 26
| GHSPictograms = {{GHS02}}{{GHS07}}
| GHSSignalWord = WARNING
| HPhrases = {{H-phrases|226|315|319}}
| PPhrases = {{P-phrases|210|302+352|305+351+338}}{{Sigma-Aldrich|sial|id=C112402|name=Cyclopentanone|access-date=2022-03-22}}
| ExternalSDS = [https://archive.org/download/Cyclopentanone-MSDS/PrintMSDSAction.pdf Cyclopentanone]
}}
|Section8={{Chembox Related
| OtherFunction_label = ketones
| OtherFunction = cyclohexanone
2-pentanone
3-pentanone
cyclopentenone
| OtherCompounds = cyclopropane
}}
}}
Cyclopentanone is the organic compound with the formula (CH2)4CO. This cyclic ketone is a colorless volatile liquid.
Preparation
Ketonic decarboxylation of adipic acid gives cyclopentanone. The reaction is conducted at elevated temperatures in the presence of barium hydroxide.{{cite journal|journal=Org. Synth.|first1=J. F.|last1=Thorpe|first2=G. A. R.|last2=Kon|year=1925|title= Cyclopentanone|volume=5|pages=37|doi=10.15227/orgsyn.005.0037}}
:File:Barium adipate pyrolysis.png
The Pd-catalyzed oxidation of cyclopentene also gives cyclopentanone.{{cite book |doi=10.1002/14356007.a08_227.pub2 |chapter=Cyclopentadiene and Cyclopentene |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2016 |last1=Claus |first1=Martin |last2=Claus |first2=Evelyn |last3=Claus |first3=Peter |last4=Hönicke |first4=Dieter |last5=Födisch |first5=Ringo |last6=Olson |first6=Michael |pages=1–16 |isbn=978-3-527-30673-2 }}
Uses
Cyclopentanone is common precursor to fragrances, especially those related to jasmine and jasmone. Examples include 2-pentyl- and 2-heptylcyclopentanone.Johannes Panten and Horst Surburg "Flavors and Fragrances, 2. Aliphatic Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2015, Wiley-VCH, Weinheim.{{doi|10.1002/14356007.t11_t01}} It is a versatile synthetic intermediate, being a precursor to cyclopentobarbital.{{cite encyclopedia |author=Hardo Siegel |author2=Manfred Eggersdorfer |title=Ketones |entry=Ketones |encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a15_077|isbn=978-3-527-30673-2}}
Cyclopentanone is also used to make cyclopentamine, the pesticide pencycuron, and pentethylcyclanone.
It is also used as a precursor to cubane-1,4-dicarboxylate, which is used to synthesize other substituted cubanes, such as the high explosives heptanitrocubane and octanitrocubane.{{Cite journal |last1=Bliese |first1=Marianne |last2=Tsanaktsidis |first2=John |date=1997 |title=Dimethyl Cubane-1,4-dicarboxylate: A Practical Laboratory Scale Synthesis |url=http://www.publish.csiro.au/?paper=C97021 |journal=Australian Journal of Chemistry |language=en |volume=50 |issue=3 |page=189 |doi=10.1071/C97021 |issn=0004-9425|url-access=subscription }}
References
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