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Cyclopentene

Organic compound; 5-sided hydrocarbon ring From Wikipedia, the free encyclopedia

Cyclopentene

Cyclopentene is a chemical compound with the formula (CH2)3(CH)2. It is a colorless liquid with a petrol-like odor. It has few applications, and thus is mainly used as a minor component of gasoline, present in concentrations of less than 1%.[1][2] It is one of the principal cycloalkenes.

Quick Facts Names, Identifiers ...
Cyclopentene
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Cyclopentene
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Ball-and-stick model of cyclopentene
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Space-filling model of cyclopentene
Names
Preferred IUPAC name
Cyclopentene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.030
UNII
  • InChI=1S/C5H8/c1-2-4-5-3-1/h1-2H,3-5H2 Y
    Key: LPIQUOYDBNQMRZ-UHFFFAOYSA-N Y
  • InChI=1/C5H8/c1-2-4-5-3-1/h1-2H,3-5H2
    Key: LPIQUOYDBNQMRZ-UHFFFAOYAS
  • C1CC=CC1
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)
ThumbHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
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).
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History and synthesis

Cyclopentene was first prepared by Carl Gärtner in 1893 from iodocyclopentane with potassium hydroxide. He named it pentamethenylene (German: Pentamethenylen).[3]

Cyclopentene is produced industrially in large amounts by steam cracking of naphtha. In the laboratory, it is prepared by dehydration of cyclopentanol.[4] Substituted cyclopentenes are the product of the vinylcyclopropane-cyclopentene rearrangement.[5]

It can also be produced by the catalytic hydrogenation of cyclopentadiene.[6]

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Reactions

The polymerization of cyclopentene by Ziegler-Natta catalysts yields 1,3-linkages, not the more typical 1,2-linked polymer.[7]

Palladium-catalyzed hydrocarboxylation of cyclopentene gives cyclopentanecarboxylic acid:[8]

C5H8 + CO + H2O → C5H9CO2H

References

External links

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