Cyclopentene

Organic compound; 5-sided hydrocarbon ring

Cyclopentene  | Cyclopentene | Ball-and-stick model of cyclopentene

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Space-filling model of cyclopentene
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

ECHA InfoCard | 100.005.030

PubChem CID

* 8882

UNII |

* ONM2CKV81Z Y

CompTox Dashboard (EPA)

* DTXSID6029171

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

| 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)  |

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

Chemical compound

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.

## History and synthesis

[edit]

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]

## Reactions

[edit]

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

[edit]

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. ISBN 978-3-527-30673-2.
2. ^ "Hydrocarbon Composition of Gasoline Vapor Emissions from Enclosed Fuel Tanks". nepis.epa.gov. United States Environmental Protection Agency. 2011.
3. ^ Gärtner, Carl (January 1893). "Das Pentamethenylen und sein Dibromür". Justus Liebigs Annalen der Chemie. 275 (2–3): 331–332\. doi:10.1002/jlac.18932750217. ISSN 0075-4617.2–3&rft.pages=331-332&rft.date=1893-01&rft_id=info:doi/10.1002/jlac.18932750217&rft.issn=0075-4617&rft.aulast=Gärtner&rft.aufirst=Carl&rft_id=https://books.google.com/books?id=QpEBhiH9p4QC&pg;=PA331&rfr_id=info:sid/en.wikipedia.org:Cyclopentene" class="Z3988">
4. ^ B. B. Corson, V. N. Ipatieff (1939). "Cyclohexylbenzene". Organic Syntheses. 19: 36. doi:10.15227/orgsyn.019.0036.
5. ^ Baldwin, John E. (2003). "Thermal Rearrangements of Vinylcyclopropanes to Cyclopentenes". Chemical Reviews. 103 (4): 1197–212\. doi:10.1021/cr010020z. PMID 12683781.
6. ^ D. Hönicke, R. Födisch, P. Claus, M. Olson: Cyclopentadiene and Cyclopentene, in: Ullmanns Enzyklopädie der Technischen Chemie 2002, Wiley-VCH, Weinheim.
7. ^ 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.
8. ^ Sang, Rui; Kucmierczyk, Peter; Dühren, Ricarda; Razzaq, Rauf; Dong, Kaiwu; Liu, Jie; Franke, Robert; Jackstell, Ralf; Beller, Matthias (2019). "Synthesis of Carboxylic Acids by Palladium‐Catalyzed Hydroxycarbonylation". Angewandte Chemie International Edition. 58 (40): 14365–14373\. doi:10.1002/anie.201908451. PMID 31390131. S2CID 199466915.

## External links

[edit]

* Media related to Cyclopentene at Wikimedia Commons

* v
* t
* e

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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