o-Cymene

o-Cymene
Names
	IUPAC name 1-methyl-2-propan-2-ylbenzene
	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,1-3H3 Key: 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/cm3
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 [77 °F], 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 most common natural isomer, o-cymene is also found naturally rarely, documented in the plant species Echinophora platyloba D.C.^[1] The three isomers form the group of cymenes.

Cymenes can be produced by alkylation of toluene with propylene.^[2]^[3]

References

^ Hashemi, Mohammad; Ehsani, Ali; Hosseini Jazani, Nima; Aliakbarlu, Javad; Mahmoudi, Razzaqh (2013). "Chemical composition and in vitro antibacterial activity of essential oil and methanol extract of Echinophora platyloba D.C against some of food-borne pathogenic bacteria". Veterinary Research Forum: An International Quarterly Journal. 4 (2): 123–127. ISSN 2008-8140. PMC 4313014. PMID 25653784.
^ 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.
^ 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 978-3527306732.

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[1] Hashemi, Mohammad; Ehsani, Ali; Hosseini Jazani, Nima; Aliakbarlu, Javad; Mahmoudi, Razzaqh (2013). "Chemical composition and in vitro antibacterial activity of essential oil and methanol extract of Echinophora platyloba D.C against some of food-borne pathogenic bacteria". Veterinary Research Forum: An International Quarterly Journal. 4 (2): 123–127. ISSN 2008-8140. PMC 4313014. PMID 25653784.

[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.

[Ullmanns-3] 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 978-3527306732.

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