Cymene

Cymene describes organic compounds with the formula CH

4CH(CH

2. Three isomers exist: 1,2- 1,3-, and 1,4-. All are colorless liquids, immiscible in water, with similar boiling points. They are classified are aromatic hydrocarbons. The bearing two substituents: an isopropyl (CH(CH

2) group and a methyl group.[1]

Cymenes

Name  | o-Cymene | m-Cymene | p-Cymene
Structural formula |  | 110px |
CAS number  | 527-84-4 | 535-77-3 | 99-87-6
melting point |  -71.54 |  -63.75 |  -67.94
boiling point (°C)  | 178.15 | 175.05 | 177.10

## Production and reactions

m- and p-Cymene are prepared by alkylation of toluene with propylene:

5 \+ 2 CH
3CH=CH
2 → CH

4CH(CH

These alkylations are catalyzed by various Lewis acids, such as aluminium trichloride.

m- and p-Cymene are mainly of interest as precursors to the respective cresols, which exploits the Hock rearrangements.[1]

## References

1. ↑ 1.0 1.1 Schmidt, Roland; Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd et al. (2014). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–74. doi:10.1002/14356007.a13_227.pub3. ISBN 9783527306732.

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Hydrocarbons

Saturated
aliphatic
hydrocarbons|

| Alkanes
CnH2n \+ 2|

| Linear alkanes|

* Methane
* Ethane
* Propane
* Butane
* Pentane
* Hexane
* Heptane
* Octane
* Nonane
* Decane

|

Branched alkanes|

* Isobutane
* Isopentane
* 3-Methylpentane
* Neopentane
* Isohexane
* Isoheptane
* Isooctane
* Isononane
* Isodecane

Cycloalkanes|

* Cyclopropane
* Cyclobutane
* Cyclopentane
* Cyclohexane
* Cycloheptane
* Cyclooctane
* Cyclononane
* Cyclodecane

Alkylcycloalkanes|

* Methylcyclopropane
* Methylcyclobutane
* Methylcyclopentane
* Methylcyclohexane
* Isopropylcyclohexane

Bicycloalkanes|

* Housane (bicyclo[2.1.0]pentane)
* Norbornane (bicyclo[2.2.1]heptane)
* Decalin (bicyclo[4.4.0]decane)

Polycycloalkanes|

* Adamantane
* Diamondoid
* Perhydrophenanthrene
* Sterane
* Cubane
* Prismane
* Dodecahedrane
* Basketane
* Churchane
* Pagodane
* Twistane

Other|

* Spiroalkanes

Unsaturated
aliphatic
hydrocarbons|

| Alkenes
CnH2n|

| Linear alkenes|

* Ethene
* Propene
* Butene
* Pentene
* Hexene
* Heptene
* Octene
* Nonene
* Decene

|

Branched alkenes|

* Isobutene
* Isopentene
* Isohexene
* Isoheptene
* Isooctene
* Isononene
* Isodecene

Alkynes
CnH2n − 2|

| Linear alkynes|

* Ethyne
* Propyne
* Butyne
* Pentyne
* Hexyne
* Heptyne
* Octyne
* Nonyne
* Decyne

|

Branched alkynes|

* Isopentyne
* Isohexyne
* Isoheptyne
* Isooctyne
* Isononyne
* Isodecyne

Cycloalkenes|

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

Alkylcycloalkenes|

* Methylcyclopropene
* Methylcyclobutene
* Methylcyclopentene
* Methylcyclohexene
* Isopropylcyclohexene

Bicycloalkenes|

* Norbornene

Cycloalkynes|

* Cyclopropyne
* Cyclobutyne
* Cyclopentyne
* Cyclohexyne
* Cycloheptyne
* Cycloctyne
* Cyclononyne
* Cyclodecyne

Dienes|

* Propadiene
* Butadiene
* Pentadiene
* Hexadiene
* Heptadiene
* Octadiene
* Nonadiene
* Decadiene

Other|

* Alkatriene
* Alkadiyne
* Cumulene
* Cyclooctatetraene
* Cyclododecatriene
* Enyne

Aromatic
hydrocarbons|

| PAHs|

| Acenes|

* Naphthalene
* Anthracene
* Tetracene
* Pentacene
* Hexacene
* Heptacene

|

Other|

* Azulene
* Fluorene
* Helicenes
* Circulenes
* Butalene
* Phenanthrene
* Chrysene
* Pyrene
* Corannulene
* Kekulene

Alkylbenzenes|

* Toluene
* Xylene
* Ethylbenzene
* Cumene
* Styrene
* Mesitylene
* Pseudocumene
* Hemellitene
* Cymene
* Hexamethylbenzene

Other|

* Benzene
* Cyclopropenylidene

Other|

* Annulenes
* Annulynes
* Alicyclic compounds
* Petroleum jelly

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