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p-Cymene

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p-Cymene
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name 1-Methyl-4-(propan-2-yl)benzene
Other names para-Cymene
4-Isopropyltoluene
4-Methylcumene
Paracymene
Identifiers
CAS Number
3D model (JSmol)
3DMet
Beilstein Reference 1903377
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.542 Edit this at Wikidata
EC Number
  • 202-796-7
Gmelin Reference 305912
KEGG
PubChem CID
RTECS number
  • GZ5950000
UNII
UN number 2046
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3Key: HFPZCAJZSCWRBC-UHFFFAOYSA-N
  • InChI=1/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3Key: HFPZCAJZSCWRBC-UHFFFAOYAD
SMILES
  • c1cc(ccc1C(C)C)C
Properties
Chemical formula C10H14
Molar mass 134.222 g·mol
Appearance Colourless liquid
Density 0.857 g/cm
Melting point −68 °C (−90 °F; 205 K)
Boiling point 177 °C (351 °F; 450 K)
Solubility in water 23.4 mg/L
Magnetic susceptibility (χ) −1.028×10 cm/mol
Refractive index (nD) 1.4908 (at 20 °C)
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
Hazard statements H226, H304, H411
Precautionary statements P210, P233, P240, P241, P242, P243, P273, P280, P301+P310, P303+P361+P353, P331, P370+P378, P391, P403+P235, P405, P501
Flash point 47 °C (117 °F; 320 K)
Autoignition
temperature
435 °C (815 °F; 708 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

p-Cymene is a naturally occurring aromatic organic compound. It is classified as an alkylbenzene related to monocyclic monoterpenes. Its structure consists of a benzene ring para-substituted with a methyl group and an isopropyl group. p-Cymene is insoluble in water, but miscible with organic solvents.

Isomers and production

In addition to p-cymene, two less common geometric isomers are 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, as expected from the terpene rule. All three isomers form the group of cymenes.

Cymene is also produced by alkylation of toluene with propene.

Related compounds

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 2. This half-sandwich compound is prepared by the reaction of ruthenium trichloride with the terpene α-phellandrene. The osmium complex is also known.

Hydrogenation gives the saturated derivative p-menthane.

References

  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. Pabst, Florian; Blochowicz, Thomas (December 2022). "On the intensity of light scattered by molecular liquids - Comparison of experiment and quantum chemical calculations". The Journal of Chemical Physics. 157 (24): 244501. Bibcode:2022JChPh.157x4501P. doi:10.1063/5.0133511. PMID 36586992.
  3. Balahbib, Abdelaali; El Omari, Nasreddine; Hachlafi, Naoufal EL.; Lakhdar, Fatima; El Menyiy, Naoual; Salhi, Najoua; Mrabti, Hanae Naceiri; Bakrim, Saad; Zengin, Gokhan; Bouyahya, Abdelhakim (2021-07-01). "Health beneficial and pharmacological properties of p-cymene". Food and Chemical Toxicology. 153: 112259. doi:10.1016/j.fct.2021.112259. ISSN 0278-6915.
  4. Vora, Bipin V.; Kocal, Joseph A.; Barger, Paul T.; Schmidt, Robert J.; Johnson, James A. (2003). "Alkylation". Kirk‐Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0112112508011313.a01.pub2. ISBN 0471238961.
  5. Bennett, M. A.; Huang, T.-N.; Matheson, T. W.; Smith, A. K. (1982). "(η-Hexamethylbenzene)Ruthenium Complexes". Inorganic Syntheses. 21: 74–78. doi:10.1002/9780470132524.ch16. ISBN 9780470132524.


Hydrocarbons
Saturated
aliphatic
hydrocarbons
Alkanes
CnH2n + 2
Linear alkanes
Branched alkanes
Cycloalkanes
Alkylcycloalkanes
Bicycloalkanes
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Unsaturated
aliphatic
hydrocarbons
Alkenes
CnH2n
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CnH2n − 2
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Alkylbenzenes
C2-Benzenes
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C3-Benzenes
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C4-Benzenes
Cymenes
Tetramethylbenzenes
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