Cyclopentene

Short description: Organic compound; 5-sided hydrocarbon ring

Cyclopentene  |

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Names
Preferred IUPAC name

Cyclopentene

Identifiers

CAS Number

* 142-29-0 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:49155 Y

ChEMBL |

* ChEMBL1797299 N

ChemSpider |

* 8544 Y

PubChem CID

* 8882

UNII |

* ONM2CKV81Z Y

InChI

* 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

SMILES

* C1CC=CC1

Properties

Chemical formula

| C

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)  |

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).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

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Cyclopentene is a chemical compound with the formula (CH

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.

## Contents

* 1 Production
* 2 Use in mechanistic organic chemistry
* 3 References
* 4 External links

## Production

Cyclopentene is produced industrially in large amounts by steam cracking of naphtha. In the laboratory, it is prepared by dehydration of cyclopentanol.[3]

It can also produced by the catalytic hydrogenation of cyclopentadiene.[4]

## 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.[5]

The polymerization of cyclopentene by Ziegler-Natta catalysts yields 1,3-linkages, not the more typical 1,2-linked polymer.[6]

## References

1. ↑ Dieter Hönicke; Ringo Födisch; Peter Claus; Michael Olson (2002). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_227.
2. ↑ "Hydrocarbon Composition of Gasoline Vapor Emissions from Enclosed Fuel Tanks". United States Environmental Protection Agency. 2011. https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=P100GPED.TXT.
3. ↑ B. B. Corson, V. N. Ipatieff (1939). "Cyclohexylbenzene". Organic Syntheses 19: 36. doi:10.15227/orgsyn.019.0036.
4. ↑ D. Hönicke, R. Födisch, P. Claus, M. Olson: Cyclopentadiene and Cyclopentene, in: Ullmanns Enzyklopädie der Technischen Chemie 2002, Wiley-VCH, Weinheim.
5. ↑ Baldwin, John E. (2003). "Thermal Rearrangements of Vinylcyclopropanes to Cyclopentenes". Chemical Reviews 103 (4): 1197–212. doi:10.1021/cr010020z. PMID 12683781.
6. ↑ 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. doi:10.1021/ma00027a039. Bibcode: 1992MaMol..25..233C.

## External links

* v
* t
* e

Cycloalkenes

Alkenes|

* Cyclopropene
* Cyclobutene
* Cyclopentene
* Cyclohexene
* Cycloheptene
* Cyclooctene
* Cyclononene

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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