Isodurene

Isodurene
Names
Preferred IUPAC name
1,2,3,5-Tetramethylbenzene
Other names
Isodurene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.653 Edit this at Wikidata
EC Number
  • 208-417-1
UNII
UN number 1993
  • InChI=1S/C10H14/c1-7-5-8(2)10(4)9(3)6-7/h5-6H,1-4H3
    Key: BFIMMTCNYPIMRN-UHFFFAOYSA-N
  • CC1=CC(=C(C(=C1)C)C)C
Properties
C10H14
Molar mass 134.22
Appearance colorless liquid
Density 0.89 g/cm3
Melting point −23.7 °C (−10.7 °F; 249.5 K)
Boiling point 198 °C (388 °F; 471 K)
27.9 mg/L
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
Flash point 63.3 °C (145.9 °F; 336.4 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Isodurene or 1,2,3,5-tetramethylbenzene is an organic compound with the formula C6H2(CH3)4, classified as an aromatic hydrocarbon. It is a flammable colorless liquid which is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar. Isodurene is one of three isomers of tetramethylbenzene, the other two being prehnitene (1,2,3,4-tetramethylbenzene) and durene (1,2,4,5-tetramethylbenzene).[1]

Preparation

Isoodurene can be prepared from mesitylene, which is converted to mesityl bromide. The latter reacts with magnesium to give the Grignard reagent, which can be alkylated with dimethyl sulfate.[2]

Industrially, isodurene can be isolated from the reformed fraction of oil refineries. It may also be produced by methylation of toluene, xylenes, and trimethylbenzenes.[1]

References

  1. ^ a b 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.
  2. ^ Lee Irvin Smith (1931). "Isoodurene". Org. Synth. 11: 66. doi:10.15227/orgsyn.011.0066.
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