P-Cymene

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Cymene
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
IUPAC name
1-Methyl-4-(1-methylethyl)benzene
Other names
4-Isopropyltoluene; Paracymene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.542 Edit this at Wikidata
EC Number
  • 202-796-7
KEGG
UNII
  • InChI=1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3 checkY
    Key: HFPZCAJZSCWRBC-UHFFFAOYSA-N checkY
  • InChI=1/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3
    Key: HFPZCAJZSCWRBC-UHFFFAOYAD
  • c1cc(ccc1C(C)C)C
Properties
C10H14
Molar mass 134.21 g/mol
Appearance Colourless liquid
Density 0.857 g/cm3
Melting point -68°C
Boiling point 177°C
23.4 mg/L
Hazards
Flash point 47°C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Cymene, or p-cymene, is a naturally occurring aromatic organic compound. It is classified as a hydrocarbon related to a monoterpene. Its structure consists of a benzene ring para-substituted with a methyl group and an isopropyl group. It is insoluble in water, but miscible with ethanol and ether.

Cymene is a constituent of a number of essential oils, most commonly the oil of cumin and thyme.

There are two less common geometric isomers. o-Cymene, in which the alkyl groups are ortho-substituted, and m-cymene, in which they are meta-substituted. p-Cymene is the only natural isomer.

Cymene is a common ligand for ruthenium. The parent compound is [(η6-cymene)RuCl2]2. This half-sandwich compound is prepared by the reaction of ruthenium trichloride with the terpene α-phellandrene. The osmium complex is also known.[1]

Significant amounts of cymene are formed in sulfite pulping process from the wood terpenes.

References

  1. ^ Bennett, M. A.; Huang, T. N.; Matheson, T. W. and Smith, A. K. (1982). "(h6-Hexamethylbenzene)ruthenium complexes". Inorganic Syntheses. 21: 74–8. doi:10.1002/9780470132524.ch16.{{cite journal}}: CS1 maint: multiple names: authors list (link)