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o-Cymene

Names
Preferred IUPAC name 1-Methyl-2-(propan-2-yl)benzene
Other names o-Cymene 2-isopropyltoluene 2-methylcumene 1-isopropyl-2-methylbenzene
Identifiers
CAS Number	527-84-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28768
ChemSpider	10253
EC Number	208-426-0
PubChem CID	10703
UNII	2T13HF3266
InChI InChI=1S/C10H14/c1-8(2)10-7-5-4-6-9(10)3/h4-8H,1-3H3Key: WWRCMNKATXZARA-UHFFFAOYSA-N
SMILES CC1=CC=CC=C1C(C)C
Properties
Chemical formula	C10H14
Molar mass	134.22
Appearance	colorless liquid
Density	0.88 g/cm
Melting point	−71.5 °C (−96.7 °F; 201.7 K)
Boiling point	178 °C (352 °F; 451 K)
Solubility in water	23.3 mg/L
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Flammable
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226
Precautionary statements	P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501
Flash point	50.6 °C (123.1 °F; 323.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

o-Cymene is an organic compound classified as an aromatic hydrocarbon. Its structure consists of a benzene ring ortho-substituted with a methyl group and an isopropyl group. It is a flammable colorless liquid which is nearly insoluble in water but soluble in organic solvents.

Isomers and production

In addition to o-cymene, there are two other geometric isomers called m-cymene, in which the alkyl groups are meta-substituted, and p-cymene, in which they are para-substituted. p-Cymene is the only isomer found in nature. The three isomers form the group of cymenes.

Cymenes can be produced by alkylation of toluene with propylene.

References

1. 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.
2. Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2002). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227. ISBN 978-3-527-30673-2.

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