p-Cymene

p-Cymene
Skeletal formula	Ball-and-stick model
Names
	Preferred IUPAC name 1-Methyl-4-(propan-2-yl)benzene[1]
	Other names para-Cymene; 4-Isopropyltoluene; 4-Methylcumene; Paracymene
Identifiers
CAS Number	99-87-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28768;
ChEMBL	ChEMBL442915 ;
ChemSpider	7183 ;
ECHA InfoCard	100.002.542
EC Number	202-796-7;
KEGG	C06575 ;
PubChem CID	7463;
UNII	1G1C8T1N7Q ;
CompTox Dashboard (EPA)	DTXSID3026645 ;
	InChI InChI=1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3 Key: HFPZCAJZSCWRBC-UHFFFAOYSA-N ; InChI=1/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3 Key: HFPZCAJZSCWRBC-UHFFFAOYAD;
	SMILES c1cc(ccc1C(C)C)C;
Properties
Chemical formula	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)
Solubility in water	23.4 mg/L
Magnetic susceptibility (χ)	−1.028×10−4 cm3/mol
Hazards
R-phrases (outdated)	R10
S-phrases (outdated)	S16
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 [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. 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 propylene.[2]

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 [(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.[3]

Hydrogenation gives the saturated derivative p-menthane.

References

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.
Vora, Bipin V.; Kocal, Joseph A.; Barger, Paul T.; Schmidt, Robert J.; Johnson, James A. (2003). "Alkylation". Kirk-Othmer Encyclopedia of Chemical Technology. Kirk‐Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0112112508011313.a01.pub2. ISBN 0471238961.
Bennett, M. A.; Huang, T.-N.; Matheson, T. W.; Smith, A. K. (1982). "(η⁶-Hexamethylbenzene)Ruthenium Complexes". Inorganic Syntheses. 21: 74–78. doi:10.1002/9780470132524.ch16.

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[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] Vora, Bipin V.; Kocal, Joseph A.; Barger, Paul T.; Schmidt, Robert J.; Johnson, James A. (2003). "Alkylation". Kirk-Othmer Encyclopedia of Chemical Technology. Kirk‐Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0112112508011313.a01.pub2. ISBN 0471238961.

[3] Bennett, M. A.; Huang, T.-N.; Matheson, T. W.; Smith, A. K. (1982). "(η⁶-Hexamethylbenzene)Ruthenium Complexes". Inorganic Syntheses. 21: 74–78. doi:10.1002/9780470132524.ch16.