p-Cymene
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Names | |||
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IUPAC name
1-Methyl-4-(1-methylethyl)benzene
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Other names
4-Isopropyltoluene; 4-Methylcumene; Paracymene
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Identifiers | |||
3D model (JSmol)
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ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.002.542 | ||
EC Number |
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KEGG | |||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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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 | |||
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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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.[1]
References
- ^ 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.