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	{{chembox		{{chembox
			|Verifiedimages = changed
	| verifiedrevid = 443548314
			|Watchedfields = changed
	| ImageFileL1_Ref = {{chemboximage|correct|??}}
			|verifiedrevid = 444653737
	| ImageFileL1=Cyclopentane2d.png
			|ImageFileL1_Ref = {{chemboximage|correct|??}}
	|ImageSizeL1=80px
			|ImageFileL1 = Cyclopentane v2.svg
	|ImageFileR1=Cyclopentane3d.png
			|ImageSizeL1 = 100px
	|ImageSizeR1=110px
			|ImageAltL1 = Skeletal formula
	|IUPACName=Cyclopentane
			|ImageFileR1 = Cyclopentane3d.png
	|OtherNames=pentamethylene
			|ImageSizeR1 = 110px
	|Section1= {{Chembox Identifiers
			|ImageAltR1 = Space-filling model
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			|PIN = Cyclopentane
	| ChemSpiderID = 8896
			|OtherNames = pentamethylene
	| InChI = 1/C5H10/c1-2-4-5-3-1/h1-5H2
			|Section1 = {{Chembox Identifiers
	| InChIKey = RGSFGYAAUTVSQA-UHFFFAOYAL
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			|ChemSpiderID = 8896
	| StdInChI = 1S/C5H10/c1-2-4-5-3-1/h1-5H2
			|InChI = 1/C5H10/c1-2-4-5-3-1/h1-5H2
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = RGSFGYAAUTVSQA-UHFFFAOYSA-N		|InChIKey = RGSFGYAAUTVSQA-UHFFFAOYAL
	| CASNo_Ref = {{cascite|correct|CAS}}		|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			|StdInChI = 1S/C5H10/c1-2-4-5-3-1/h1-5H2
	| CASNo=287-92-3
			|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| PubChem=9253
			|StdInChIKey = RGSFGYAAUTVSQA-UHFFFAOYSA-N
	| ChEBI_Ref = {{ebicite|correct|EBI}}
			|CASNo_Ref = {{cascite|correct|CAS}}
	| ChEBI = 23492
			|CASNo=287-92-3
	| SMILES=C1CCCC1
			|UNII_Ref = {{fdacite|correct|FDA}}
	| RTECS=GY2390000
			|UNII = T86PB90RNU
	}}
			|PubChem=9253
	|Section2= {{Chembox Properties
			|ChEBI_Ref = {{ebicite|correct|EBI}}
	| Formula=C<sub>5</sub>H<sub>10</sub>
			|ChEBI = 23492
	| MolarMass=70.1 g/mol
			|SMILES=C1CCCC1
	| Appearance=clear, colorless liquid
			|RTECS=GY2390000
	| Density=0.751 g/cm<sup>3</sup>
			|EINECS = 206-016-6
	| MeltingPt=−94 °C
	| BoilingPtC=49
	| Solubility=
	| pKa = ~45
	| pKb =
	}}
	|Section3= {{Chembox Hazards
	| MainHazards=
	| FlashPt=
	| Autoignition=
	}}
	| Section8 = {{Chembox Related
	| OtherCpds = ], ], ]
	}}
	}}		}}
			|Section2 = {{Chembox Properties
	'''Cyclopentane''' is a highly ] ] ] with ] {{carbon}}<sub>5</sub>{{hydrogen}}<sub>10</sub> and ] 287-92-3, consisting of a ring of five ] atoms each bonded with two ] atoms above and below the plane. It occurs as a colorless ] with a ]-like ]. Its ] is −94 °C and its ] is 49 °C. Cyclopentane is in the class of ]s, being ]s which have one or more ].
			|Formula=C<sub>5</sub>H<sub>10</sub>
	]
			|MolarMass=70.1 g/mol
			|Appearance=clear, colorless liquid
			|Odor = mild, sweet
			|Density=0.751 g/cm<sup>3</sup>
			|MeltingPtC=-93.9
			|BoilingPtC=49.2
			|Solubility=156 mg·l<sup>−1</sup> (25 °C)<ref>{{GESTIS|ZVG=27960|CAS=287-92-3|Name=cyclopentane|Date=28 February 2015}}</ref>
			|SolubleOther = soluble in ], ], ]
			|pKa = ~45
			|RefractIndex = 1.4065
			|VaporPressure = 45 ] (20 °C) <ref>{{cite web |url=http://www.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=0353 |title = ICSC 0353 - CYCLOPENTANE}}</ref>
			|MagSus = -59.18·10<sup>−6</sup> cm<sup>3</sup>/mol
			}}
			|Section3 = {{Chembox Hazards
			|MainHazards=Flammable<ref name=PGCH/>
			|FlashPtC = -37.2
			|AutoignitionPtC = 361
			|NFPA-H = 1 | NFPA-F = 3 | NFPA-R = 0
			|PEL = none<ref name=PGCH>{{PGCH|0171}}</ref>
			|ExploLimits = 1.1%-8.7%<ref name=PGCH/>
			|IDLH = N.D.<ref name=PGCH/>
			|REL = TWA 600 ppm (1720 mg/m<sup>3</sup>)<ref name=PGCH/>
			}}
			|Section4 = {{Chembox Related
			|OtherCompounds = ], ], ]
			}}
			}}
			'''Cyclopentane''' (also called '''C pentane''')<ref>{{cite journal |last1=Sárkány |first1=A. |last2=Gaál |first2=J. |last3=Toth |first3=L. |title=Comparative Study of C-Pentane and N-Pentane Transformations on Ni and Pt Catalysts |journal=Studies in Surface Science and Catalysis |date=1981 |volume=7 |pages=291–301 |doi=10.1016/S0167-2991(09)60278-0}}</ref> is a highly ] ] ] with ] ] and ] 287-92-3, consisting of a ring of five ] atoms each bonded with two ] atoms above and below the plane. It is a colorless ] with a ]-like ]. Its ] is −94 °C and its ] is 49 °C. Cyclopentane is in the class of ]s, being ]s that have one or more ]s. It is formed by ] ] in the presence of ] at a high temperature and pressure.
			It was first prepared in 1893 by the German chemist ].<ref>{{cite journal |last1=Wislicenus |first1=J. |last2=Hentschel |first2=W. |title=III. Der Pentamethenylalkohol und seine Derivate (Cyclopentanol and its derivatives)|journal=Justus Liebigs Annalen der Chemie |date=January 1893 |volume=275 |issue=2-3 |pages=322–330 |doi=10.1002/jlac.18932750216 | url=https://zenodo.org/records/1657308/files/article.pdf}}</ref>
	==Industrial usage==
	Cyclopentane is used in the manufacture of ] ]s and ] ]s and also as a ] in the manufacture of ] insulating foam, as found in many domestic appliances such as ]s and ]s, replacing environmentally damaging alternatives such as ] and ]<ref name=greenpeace> Greenpeace - Appliance Insulation</ref>
			==Production, occurrence and use==
	More advanced technologies, such as computer hard drives and outerspace equipment employ multiply alkylated cyclopentane (MAC) lubricants because of their extremely low volatility.<ref name=pennzane> Pennzane - lubrication technology</ref>
			Cycloalkanes are formed by ]. For example, when passed over a hot platinum surface, ] converts into cyclopentane.
			]
	The ] produces more than half a million kilograms of this chemical per year.
			Cyclopentane is principally used as a ] in the manufacture of ], replacing ozone-depleting agents such as ] and ].<ref name="Schilling2000">{{cite journal | last1 = Schilling | first1 = S. L. | title = Appliance Rigid Foams Blown with Cyclopentane and Cyclopentane/Isopentane Blends | journal = Journal of Cellular Plastics | date = May 2000 | volume = 36 | issue = 3 | pages = 190–206 | issn = 0021-955X | eissn = 1530-7999 | doi = 10.1177/0021955X0003600302 | pmid = | url = }}</ref><ref name=greenpeace> {{webarchive|url=https://web.archive.org/web/20081030041552/http://archive.greenpeace.org/ozone/excuse/20excuse.html |date=2008-10-30 }}</ref> While cyclopentane is not typically used as a ], it is common for domestic appliances that are insulated with cyclopentane-based foam, such as ]s and ]s, to be marked with cyclopentane warning labels due to its flammability. Cyclopentane is also used in the manufacture of ] ]s and ] ]s.{{Citation needed|date=June 2024}}
			Cyclopentane is a minor component of automobile fuel, with its share in US ] varying between 0.2 and 1.6% in early 1990s<ref>{{Cite journal |last=Doskey |first=Paul V. |last2=Porter |first2=Joseph A. |last3=Scheff |first3=Peter A. |date=November 1992 |title=Source Fingerprints for Volatile Non-Methane Hydrocarbons |url=https://www.tandfonline.com/doi/full/10.1080/10473289.1992.10467090 |journal=Journal of the Air & Waste Management Association |language=en |volume=42 |issue=11 |pages=1437–1445 |doi=10.1080/10473289.1992.10467090 |issn=1047-3289}}</ref> and 0.1 to 1.7% in 2011<ref>{{cite web |date=2011 |title=Hydrocarbon Composition of Gasoline Vapor Emissions from Enclosed Fuel Tanks |url=https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=P100GPED.TXT |website=nepis.epa.gov |publisher=United States Environmental Protection Agency}}</ref>. Its research and motor ] are reported as 101 or 103 and 85 or 86 respectively.<ref>{{Cite book |last=Scherzer |first=Julius |url=https://books.google.com/books?id=0R2qSCsVT3cC&pg=PA9 |title=Octane-Enhancing Zeolitic FCC Catalysts: Scientific and Technical Aspects |date=1990-08-31 |publisher=CRC Press |isbn=978-0-8247-8399-0 |pages=9 |language=en}}</ref><ref>{{Cite journal |last=Song |first=Hwasup |last2=Dauphin |first2=Roland |last3=Vanhove |first3=Guillaume |date=2020 |title=A kinetic investigation on the synergistic low-temperature reactivity, antagonistic RON blending of high-octane fuels: Diisobutylene and cyclopentane |url=https://www.researchgate.net/publication/342664049_A_kinetic_investigation_on_the_synergistic_low-temperature_reactivity_antagonistic_RON_blending_of_high-octane_fuels_Diisobutylene_and_cyclopentane |journal=Combustion and Flame |volume=220 |pages=23–33 |doi=10.1016/j.combustflame.2020.06.030 |issn=0010-2180}}</ref>
	==Formulation of cycloalkanes==
			Multiple alkylated cyclopentane (MAC) lubricants, such as 1,3,4-tri-(2-octyldodecyl) cyclopentane, have low volatility and are used by NASA in space applications.<ref name="NASA">{{cite tech report |last1=Loewenthal |first1=Stuart H. |last2=Jones |first2=William R. |last3=Predmore |first3=Roamer E. |title=Life of Pennzane and 815Z-Lubricated Instrument Bearings Cleaned with Non-CFC Solvents |date=1 September 1999 |url=https://ntrs.nasa.gov/citations/19990039657 |publisher=National Aeronautics and Space Administration |location=John H. Glenn Research Center at Lewis Field |language=en |oclc=1002210567 |id=19990039657 }}</ref><ref>{{cite web | title=Pennzoil Products: High Tech Products | website=pennzane.com | date=12 April 2004 | url=http://pennzane.com/ | archive-url=https://web.archive.org/web/20040412141718/http://pennzane.com/ | archive-date=12 April 2004 | url-status=dead | access-date=15 July 2022}}</ref>
	Cycloalkanes can be formulated via a process known as ].
			Cyclopentane requires safety precautions to prevent leakage and ignition as it is both highly flammable and can also cause respiratory arrest when inhaled.<ref>{{cite journal | author=Robert W. Virtue, M.D. | title=OBSERVATIONS ON CYCLOPENTANE AS AN ANESTHETIC AGENT | journal=Anesthesiology | volume=10 | date=May 1949 | pages=318–324 | doi=10.1097/00000542-194905000-00007}}</ref>
	For example, 2-methylbutane can be reformed into cyclopentane, by use of a platinum catalyst. This is particularly well known in automobiles, as branched alkanes will burn much more readily.
			Cyclopentane can be fluorinated to give compounds ranging from {{chem2|C5H9F}} to ] {{chem2|C5F10}}. Such species are conceivable refrigerants and specialty solvents.<ref name="Tatlow 1995">{{cite journal | last=Tatlow | first=John Colin | title=Cyclic and bicyclic polyfluoro-alkanes and -alkenes | journal=Journal of Fluorine Chemistry | volume=75 | issue=1 | year=1995 | issn=0022-1139 | doi=10.1016/0022-1139(95)03293-m | pages=7–34}}</ref><ref>{{cite journal |last1=Zhang |first1=Chengping |last2=Qing |first2=Feiyao |last3=Quan |first3=Hengdao |last4=Sekiya |first4=Akira |title=Synthesis of 1,1,2,2,3,3,4-heptafluorocyclopentane as a new generation of green solvent |journal=Journal of Fluorine Chemistry |date=January 2016 |volume=181 |pages=11–16 |doi=10.1016/j.jfluchem.2015.10.012}}</ref>
			The cyclopentane ring is pervasive in ]s including many useful drugs. Examples include most ]s, ]s, and some ]s.
			==Conformations==
			In a ], the angles at the vertices are all 108°, slightly less than the bond angle in perfectly tetrahedrally bonded carbon, which is about 109.47°. However, cyclopentane is not planar in its normal ]. It puckers in order to increase the distances between the hydrogen atoms (something which does not happen in the planar ] {{chem2|C5H5-}} because it doesn't have as many hydrogen atoms). This means that the average C-C-C angle is less than 108°. There are two conformations that give local minima of the energy, the "envelope" and the "half-chair". The envelope has mirror symmetry (]), while the half chair has two-fold rotational symmetry (]). In both cases the symmetry implies that there are two pairs of equal C-C-C angles and one C-C-C angle that has no pair. In fact for cyclopentane, unlike for ] (C<sub>6</sub>H<sub>12</sub>, see ]) and higher ]s, it is not possible geometrically for all the angles and bond lengths to be equal except if it is in the form of a flat regular pentagon.
			<gallery>
			File:Cyclopentane envelope conformation.svg|Envelope
			File:Cyclopentane3D.png|3D envelope
			File:Cyclopentane halfchair.svg|Half-chair
			</gallery>
	==References==		==References==
	{{reflist}}		{{reflist}}
			==External links==
			*{{Commons category-inline|Cyclopentane}}
	{{cycloalkanes}}		{{cycloalkanes}}
			{{Authority control}}
			]
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