Prehnitene

Prehnitene
Names
	Preferred IUPAC name 1,2,3,4-Tetramethylbenzene
	Other names Prehnitene
Identifiers
CAS Number	488-23-3;
3D model (JSmol)	Interactive image;
Beilstein Reference	1904390
ChEBI	CHEBI:38997;
ChEMBL	ChEMBL1797278;
ChemSpider	9844;
ECHA InfoCard	100.006.976
EC Number	207-673-1;
Gmelin Reference	101866
PubChem CID	10263;
UNII	96WT7D2WXJ;
CompTox Dashboard (EPA)	DTXSID4060072 ;
	InChI InChI=1S/C10H14/c1-7-5-6-8(2)10(4)9(7)3/h5-6H,1-4H3 Key: UOHMMEJUHBCKEE-UHFFFAOYSA-N;
	SMILES CC1=C(C(=C(C=C1)C)C)C;
Properties
Chemical formula	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)
Solubility in water	33.9 mg/l
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Flammable
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references

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 E_1/2 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

^ ^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 978-3527306732.
^ 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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[Ullmanns-1] 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.

[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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