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| Names | |||
|---|---|---|---|
| Preferred IUPAC name Cyclopentene | |||
| Identifiers | |||
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3D model (JSmol) | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
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| ECHA InfoCard | 100.005.030 | ||
| UNII | |||
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| 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) | |||
| Flash point | −29 °C (−20 °F; 244 K) | ||
| Related compounds | |||
Related compounds | Cyclopentadiene Cyclobutene | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Cyclopentene is achemical compound with the formula(CH2)3(CH)2. It is a colorlessliquid with apetrol-likeodor. 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 principalcycloalkenes.
Cyclopentene was first prepared by Carl Gärtner in 1893 from iodocyclopentane withpotassium hydroxide. He named itpentamethenylene (German:Pentamethenylen).[3]
Cyclopentene is produced industrially in large amounts bysteam cracking ofnaphtha. In the laboratory, it is prepared by dehydration ofcyclopentanol.[4] Substituted cyclopentenes are the product of thevinylcyclopropane-cyclopentene rearrangement.[5]
It can also be produced by thecatalytic hydrogenation ofcyclopentadiene.[6]
The polymerization of cyclopentene byZiegler-Natta catalysts yields 1,3-linkages, not the more typical 1,2-linked polymer.[7]
Palladium-catalyzedhydrocarboxylation of cyclopentene givescyclopentanecarboxylic acid:[8]
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