Methylcyclopentane is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the

chemical formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as pare ...

CH₃C₅ H₉. It is a colourless, flammable liquid with a faint odor. It is a component of the naphthene fraction of petroleum usually obtained as a mixture with

cyclohexane Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexan ...

. It is mainly converted in naphthene reformers to

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

. As of early 1990s, it was present in American and European

gasoline Gasoline ( North American English) or petrol ( Commonwealth English) is a petrochemical product characterized as a transparent, yellowish, and flammable liquid normally used as a fuel for spark-ignited internal combustion engines. When for ...

in small amounts, and by 2011 its share in US gasoline varied between 1 and 3%. It has a research octane number of 103 and motor octane number of 95. The C₆ core of methylcyclopentane is not perfectly planar and can pucker to alleviate stress in its structure. : MeC5H9toPhH

History

Methylcyclopentane was first synthesized in 1888 by and W. H. Perkin Jr. by a Wurtz reaction of

sodium Sodium is a chemical element; it has Symbol (chemistry), symbol Na (from Neo-Latin ) and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 element, group 1 of the peri ...

and 1,5-dibromohexane. They named it methylpentamethylene since the modern nomenclature wasn't developed until 1892 Geneva Rules. In 1895, Nikolai Kischner discovered that methylcyclopentane was the reaction product of hydrogenation of

using hydriodic acid. Prior to that, several chemists (such as Marcellin Berthelot in 1867, and

Adolf von Baeyer Johann Friedrich Wilhelm Adolf von Baeyer (; 31 October 1835 – 20 August 1917) was a German chemist who synthesised indigo dye, indigo and developed a Von Baeyer nomenclature, nomenclature for cyclic compounds (that was subsequently extended a ...

in 1870) had tried and failed to synthesize

using this method.

References

{{Authority control Cycloalkanes Cyclopentyl compounds Methyl compounds