p-Cymene

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p-Cymene
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
1-Methyl-4-(propan-2-yl)benzene
Other names
p-Cymene (no longer recommended[1])
4-Isopropyltoluene
4-Methylcumene
Paracymene
Identifiers
99-87-6 YesY
ChEBI CHEBI:28768
ChEMBL ChEMBL442915 YesY
ChemSpider 7183 YesY
EC Number 202-796-7
Jmol 3D model Interactive image
KEGG C06575 YesY
PubChem 7463
UNII 1G1C8T1N7Q YesY
Properties
C10H14
Molar mass 134.21 g/mol
Appearance Colourless liquid
Density 0.857 g/cm3
Melting point −68 °C (−90 °F; 205 K)
Boiling point 177 °C (351 °F; 450 K)
23.4 mg/L
Hazards
R-phrases R10
S-phrases S16
Flash point 47 °C (117 °F; 320 K)
435 °C (815 °F; 708 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

p-Cymene is a naturally occurring aromatic organic compound. It is classified as an alkylbenzene related to a monoterpene. Its structure consists of a benzene ring para-substituted with a methyl group and an isopropyl group. 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. All three isomers form the group of cymenes.

p-Cymene is insoluble in water, but miscible with ethanol and diethyl ether.

It is a constituent of a number of essential oils, most commonly the oil of cumin and thyme. Significant amounts are formed in sulfite pulping process from the wood terpenes.

p-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.[2]

References[edit]

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 139, 597. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. 
  2. ^ M. A. Bennett; T.-N. Huang; T. W. Matheson; A. K. Smith; Steven Ittel; William Nickerson (1982). "(η6-Hexamethylbenzene)Ruthenium Complexes". Inorganic Syntheses. 21: 74–78. doi:10.1002/9780470132524.ch16.