Cyclopentanone: Difference between revisions

| Verifiedimages = changed

| Watchedfields = changed

| verifiedrevid = 443548992

| Reference=<ref>''[[Merck Index]]'', 11th Edition, '''2748'''.</ref>

| 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 <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->

| OtherNames = Ketocyclopentane<br />Adipic ketone

|Section1={{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 220W81TN3S

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| 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

|Section3={{Chembox Structure

| Dipole =

|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}}<ref name="sigma">{{Sigma-Aldrich|sial|id=C112402|name=Cyclopentanone|access-date=2022-03-22}}</ref>

| ExternalSDS = [https://archive.org/download/Cyclopentanone-MSDS/PrintMSDSAction.pdf Cyclopentanone]

|Section8={{Chembox Related

| OtherFunction_label = [[ketone]]s

| OtherFunction = [[cyclohexanone]]<br />[[2-Pentanone|2-pentanone]]<br />[[3-pentanone]]<br />[[cyclopentenone]]

| OtherCompounds = [[cyclopropane]]

'''Cyclopentanone''' is the [[organic compound]] with the formula (CH₂)₄CO. This cyclic [[ketone]] is a colorless volatile liquid.

==Preparation==

Upon treatment with [[barium hydroxide]] at elevated temperatures, [[adipic acid]] undergoes [[ketonization]] to give cyclopentanone:<ref>{{OrgSynth|author=J. F. Thorpe and G. A. R. Kon|year=1925|title=Cyclopentanone|volume=5|page=37|collvol=1|collvolpages=192|prep=CV1P0192}}.</ref>

:(CH₂)₄(CO₂H)₂ → (CH₂)₄CO + H₂O + CO₂

==Uses==

Cyclopentanone is common precursor to fragrances, especially those related to [[jasmine]] and [[jasmone]]. Examples include 2-pentyl- and 2-heptylcyclopentanone.<ref>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}}</ref> It is a versatile synthetic intermediate, being a precursor to [[cyclopentobarbital]].<ref name=Ullmann>{{cite encyclopedia |author=Hardo Siegel |author2=Manfred Eggersdorfer |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 }}</ref>

[[File:Cyclopal.svg|thumb|left|144px|Cyclopentobarbital is a drug made from cyclopentanone.]]

Cyclopentanone is also used to make [[cyclopentamine]], the pesticide [[pencycuron]], and [[pentethylcyclanone]].<ref name=Ullmann/>

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|octonitrocubane]].<ref>{{Cite journal |last=Bliese |first=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}}</ref>

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[[Category:Cycloalkanones|5]]

[[Category:Ketone solvents]]

[[Category:Perfume ingredients]]

[[Category:Cyclopentanes]]