Isodurene

Isodurene
Names
	Preferred IUPAC name 1,2,3,5-Tetramethylbenzene
	Other names Isodurene
Identifiers
CAS Number	527-53-7;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1797133;
ChemSpider	10245;
ECHA InfoCard	100.007.653
EC Number	208-417-1;
PubChem CID	10695;
UNII	0JBI5Y5A5Z;
UN number	1993
CompTox Dashboard (EPA)	DTXSID6026119 ;
	InChI InChI=1S/C10H14/c1-7-5-8(2)10(4)9(3)6-7/h5-6H,1-4H3 Key: BFIMMTCNYPIMRN-UHFFFAOYSA-N;
	SMILES CC1=CC(=C(C(=C1)C)C)C;
Properties
Chemical formula	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)
Solubility in water	27.9 mg/L
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Flammable
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319
Precautionary statements	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). Infobox references

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

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

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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] Lee Irvin Smith (1931). "Isoodurene". Org. Synth. 11: 66. doi:10.15227/orgsyn.011.0066.

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