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Chemical compound From Wikipedia, the free encyclopedia
p-Cymene is a naturally occurring aromatic organic compound. It is classified as an alkylbenzene related to monocyclic monoterpenes.[3] 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.
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Names | |||
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Preferred IUPAC name
1-Methyl-4-(propan-2-yl)benzene[1] | |||
Other names
para-Cymene 4-Isopropyltoluene 4-Methylcumene Paracymene | |||
Identifiers | |||
3D model (JSmol) |
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3DMet | |||
1903377 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.002.542 | ||
EC Number |
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305912 | |||
KEGG | |||
PubChem CID |
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RTECS number |
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UNII | |||
UN number | 2046 | ||
CompTox Dashboard (EPA) |
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Properties | |||
C10H14 | |||
Molar mass | 134.222 g·mol−1 | ||
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 | |||
−1.028×10−4 cm3/mol | |||
Refractive index (nD) |
1.4908 (at 20 °C) [2] | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H226, H304, H411 | |||
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) | ||
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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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.[4]
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.[5]
Hydrogenation gives the saturated derivative p-menthane.
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