Cyclopentene

Cyclopentene
Names
	Preferred IUPAC name Cyclopentene
Identifiers
CAS Number	142-29-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:49155 ;
ChEMBL	ChEMBL1797299 ;
ChemSpider	8544 ;
ECHA InfoCard	100.005.030
PubChem CID	8882;
UNII	ONM2CKV81Z ;
CompTox Dashboard (EPA)	DTXSID6029171 ;
	show InChI
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Properties
Chemical formula	C5H8
Molar mass	68.11 g/mol
Density	0.771 g/cm3
Melting point	−135 °C (−211 °F; 138 K)
Boiling point	44 to 46 °C (111 to 115 °F; 317 to 319 K)
Hazards
NFPA 704 (fire diamond)	1 3 1
Flash point	−29 °C (−20 °F; 244 K)
Related compounds
Related compounds	Cyclopentadiene; Cyclobutene
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	(what is ?)
	Infobox references

Cyclopentene is a chemical compound with the formula (CH₂)₃(CH)₂. It is a colorless liquid with a petrol-like odor. It is one of the cycloalkenes. Cyclopentene is produced industrially in large amounts by steam cracking of naphtha. It has few applications, and thus is mainly used as a component of gasoline.^[1]

Use in mechanistic organic chemistry[]

Cyclopentene is used in analysing the mechanisms of organic reactions. It can be obtained from vinylcyclopropane in the vinylcyclopropane-cyclopentene rearrangement.^[2]

The polymerization of cyclopentene by Ziegler-Natta catalysts yields 1,3-linkages, not the more typical 1,2-linked polymer.^[3]

References[]

^ Dieter Hönicke; Ringo Födisch; Peter Claus; Michael Olson (2002). "Cyclopentadiene and Cyclopentene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_227.
^ Baldwin, John E. (2003). "Thermal Rearrangements of Vinylcyclopropanes to Cyclopentenes". Chemical Reviews. 103 (4): 1197–212. doi:10.1021/cr010020z. PMID 12683781.
^ Collins, Scott; Kelly, W. Mark (1992). "The microstructure of poly(cyclopentene) produced by polymerization of cyclopentene with homogeneous Ziegler-Natta catalysts". Macromolecules. 25 (1): 233–7. Bibcode:1992MaMol..25..233C. doi:10.1021/ma00027a039.

External links[]

Media related to Cyclopentene at Wikimedia Commons

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[1] Dieter Hönicke; Ringo Födisch; Peter Claus; Michael Olson (2002). "Cyclopentadiene and Cyclopentene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_227.

[CR-2] Baldwin, John E. (2003). "Thermal Rearrangements of Vinylcyclopropanes to Cyclopentenes". Chemical Reviews. 103 (4): 1197–212. doi:10.1021/cr010020z. PMID 12683781.

[3] Collins, Scott; Kelly, W. Mark (1992). "The microstructure of poly(cyclopentene) produced by polymerization of cyclopentene with homogeneous Ziegler-Natta catalysts". Macromolecules. 25 (1): 233–7. Bibcode:1992MaMol..25..233C. doi:10.1021/ma00027a039.

[1]

[2]

[3]

show v t Cycloalkenes
Alkenes	Cyclopropene Cyclobutene Cyclopentene Cyclohexene Cycloheptene Cyclooctene Cyclononene Cyclodecene
Dienes	Cyclobutadiene Cyclopentadiene Cyclohexadiene 1,3-Cyclohexadiene 1,4-Cyclohexadiene Cycloheptadiene 1,3-Cycloheptadiene 1,4-Cycloheptadiene Cyclooctadiene 1,5-Cyclooctadiene
Trienes	Benzene Cycloheptatriene
Tetraenes	Cyclooctatetraene Cyclononatetraene

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