M-Cymene

m-Cymene
Names
Preferred IUPAC name
1-Methyl-3-(propan-2-yl)benzene
Other names
  • m-Cymene
  • 3-isopropyltoluene
  • 3-methylcumene
  • 1-isopropyl-3-methylbenzene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 208-617-9
UNII
  • InChI=1S/C10H14/c1-8(2)10-6-4-5-9(3)7-10/h4-8H,1-3H3
    Key: XCYJPXQACVEIOS-UHFFFAOYSA-N
  • CC1=CC(=CC=C1)C(C)C
Properties
C10H14
Molar mass 134.22
Appearance colorless liquid
Density 0.86 g/cm3
Melting point −63.8 °C (−82.8 °F; 209.3 K)
Boiling point 175 °C (347 °F; 448 K)
42.5 mg/L
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable
GHS labelling:
GHS02: Flammable
Warning
H226
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501
Flash point 47.8 °C (118.0 °F; 320.9 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

m-Cymene is an organic compound classified as an aromatic hydrocarbon. Its structure consists of a benzene ring meta-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 m-cymene, there are two other geometric isomers called o-cymene, in which the alkyl groups are ortho-substituted, and p-cymene, in which they are para-substituted. p-Cymene is the most common and only natural isomer. The three isomers form the group of cymenes.

Cymenes can be produced by alkylation of toluene with propylene.[1][2]

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. 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 978-3527306732.
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