Cyclopentene

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]

Cyclopentene
Cyclopentene
Ball-and-stick model of cyclopentene
Names
IUPAC name
Cyclopentene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.030
UNII
Properties
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)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
1
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).
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Infobox references

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]

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References
  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.CS1 maint: multiple names: authors list (link)
  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: 233-7. doi:10.1021/ma00027a039.CS1 maint: multiple names: authors list (link)
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