# Cymene

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{{for|the ancient Greek city|Cymene (Thessaly)}}
'''Cymene''' describes [organic compound](/source/organic_compound)s with the formula {{chem2|CH3C6H4CH(CH3)2}}.  Three isomers exist: 1,2- 1,3-, and 1,4-.  All are colorless liquids, [immiscible](/source/immiscible) in water, with similar [boiling point](/source/boiling_point)s. They are classified as [aromatic](/source/aromatic) [hydrocarbon](/source/hydrocarbon)s.  They bear two substituents: an [isopropyl](/source/isopropyl) ({{chem2|CH(CH3)2}}) group and a [methyl group](/source/methyl_group).<ref name=HC>{{cite book |doi=10.1002/14356007.a13_227.pub3 |chapter=Hydrocarbons |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2014 |last1=Schmidt |first1=Roland |last2=Griesbaum |first2=Karl |last3=Behr |first3=Arno |last4=Biedenkapp |first4=Dieter |last5=Voges |first5=Heinz-Werner |last6=Garbe |first6=Dorothea |last7=Paetz |first7=Christian |last8=Collin |first8=Gerd |last9=Mayer |first9=Dieter |last10=Höke |first10=Hartmut |pages=1–74 |isbn=9783527306732 }}</ref>
{|class="wikitable" style="text-align:center; font-size:90%"
| colspan="4" class="colspan=&quot;4&quot;" | '''Cymenes'''
|-
! Name
| [''o''-Cymene](/source/o-Cymene) || [''m''-Cymene](/source/m-Cymene) || [''p''-Cymene](/source/p-Cymene)
|-
! [Structural formula](/source/Structural_formula)
| 110px || 110px || 90px
|-
! [CAS number](/source/CAS_number)
| 527-84-4 || 535-77-3 || 99–87–6
|-
! [melting point](/source/melting_point) (°C)
| −71.54 || −63.75 || −67.94
|-
! [boiling point](/source/boiling_point) (°C)
| 178.15 || 175.05 ||177.10
|}

==Production and reactions==
m- and p-Cymene are prepared by [alkylation](/source/alkylation) of [toluene](/source/toluene) with [propylene](/source/propylene):
:{{chem2|CH3C6H5  +  2 CH3CH\dCH2  ->  CH3C6H4CH(CH3)2}}
These alkylations are catalyzed by various [Lewis acid](/source/Lewis_acid)s, such as [aluminium trichloride](/source/aluminium_trichloride).

m- and p-Cymene are mainly of interest as precursors to the respective [cresol](/source/cresol)s, which exploits the [Hock rearrangement](/source/Hock_rearrangement)s.<ref name=HC/>

==References==
{{Reflist}}

{{Hydrocarbons}}

Category:Alkylbenzenes
Category:C4-Benzenes
Category:Monoterpenes
Category:Isopropyl compounds

{{Organic-chem-stub}}

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Adapted from the Wikipedia article [Cymene](https://en.wikipedia.org/wiki/Cymene) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Cymene?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.