O-Cymene: Difference between revisions

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,1-3H3 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

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Revision as of 23:59, 4 May 2022

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.^[1]^[2]

References

^ 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.

This article about a hydrocarbon is a stub. You can help Wikipedia by expanding it.

[1] 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-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 978-3527306732.

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[2]

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 == Isomers and production ==
-In addition to ''o''-cymene, there are two other geometric isomers called [[M-Cymene|''m''-cymene]], in which the alkyl groups are ''meta''-substituted, and [[P-Cymene|''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|Echinophora platyloba]]'' D.C.<ref>{{Cite journal|last=Hashemi|first=Mohammad|last2=Ehsani|first2=Ali|last3=Hosseini Jazani|first3=Nima|last4=Aliakbarlu|first4=Javad|last5=Mahmoudi|first5=Razzaqh|date=2013|title=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|url=https://pubmed.ncbi.nlm.nih.gov/25653784/|journal=Veterinary Research Forum: An International Quarterly Journal|volume=4|issue=2|pages=123–127|issn=2008-8140|pmc=4313014|pmid=25653784}}</ref> The three isomers form the group of [[cymenes]].
+In addition to ''o''-cymene, there are two other geometric isomers called [[M-Cymene|''m''-cymene]], in which the alkyl groups are ''meta''-substituted, and [[P-Cymene|''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]].<ref>{{cite encyclopedia|chapter=Alkylation|first1=Bipin V.|title=Kirk-Othmer Encyclopedia of Chemical Technology|last1=Vora|first2=Joseph A.|last2=Kocal|first3=Paul T.|last3=Barger|first4=Robert J.|last4=Schmidt|first5=James A.|last5=Johnson|year=2003|encyclopedia=Kirk‐Othmer Encyclopedia of Chemical Technology|doi=10.1002/0471238961.0112112508011313.a01.pub2|isbn=0471238961}}</ref><ref name=Ullmanns>{{Ullmann|first1 = Karl|last1 = Griesbaum|first2 = Arno|last2 = Behr|first3 = Dieter|last3 = Biedenkapp|first4 = Heinz-Werner|last4 = Voges|first5 = Dorothea|last5 = Garbe|first6 = Christian|last6 = Paetz|first7 = Gerd|last7 = Collin|first8 = Dieter|last8 = Mayer|first9 = Hartmut|last9 = Höke|title = Hydrocarbons|year = 2002|doi = 10.1002/14356007.a13_227}}</ref>