Prehnitene

Prehnitene
Names
Preferred IUPAC name
1,2,3,4-Tetramethylbenzene
Other names
Prehnitene
Identifiers
3D model (JSmol)
1904390
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.976 Edit this at Wikidata
EC Number
  • 207-673-1
101866
UNII
  • InChI=1S/C10H14/c1-7-5-6-8(2)10(4)9(7)3/h5-6H,1-4H3
    Key: UOHMMEJUHBCKEE-UHFFFAOYSA-N
  • CC1=C(C(=C(C=C1)C)C)C
Properties
C10H14
Molar mass 134.22
Appearance colorless liquid
Density 0.90 g/cm3
Melting point −6.2 °C (20.8 °F; 266.9 K)
Boiling point 205 °C (401 °F; 478 K)
33.9 mg/l
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point 68.3 °C (154.9 °F; 341.4 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Prehnitene or 1,2,3,4-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. Prehnitene is one of three isomers of tetramethylbenzene, the other two being isodurene (1,2,3,5-tetramethylbenzene) and durene (1,2,4,5-tetramethylbenzene).[1] It is a relatively easily oxidized benzene derivative, with E1/2 of 2.0 V vs NHE.[2]

Production

Industrially, prehnitene can be isolated from the reformed fraction of oil refineries. It may also be produced by methylation of toluene, xylenes and the trimethylbenzenes hemimellitene and pseudocumene.[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. ^ Howell, J. O.; Goncalves, J. M.; Amatore, C.; Klasinc, L.; Wightman, R. M.; Kochi, J. K. (1984). "Electron transfer from aromatic hydrocarbons and their pi-complexes with metals. Comparison of the standard oxidation potentials and vertical ionization potentials". Journal of the American Chemical Society. 106 (14): 3968–3976. doi:10.1021/ja00326a014.
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