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Isodurene

From Wikipedia, the free encyclopedia
Organic compound
Isodurene
Names
Preferred IUPAC name
1,2,3,5-Tetramethylbenzene
Other names
Isodurene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard100.007.653Edit this at Wikidata
EC Number
  • 208-417-1
UNII
UN number1993
  • 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 mass134.22
Appearancecolorless liquid
Density0.89 g/cm3
Melting point−23.7 °C (−10.7 °F; 249.5 K)
Boiling point198 °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 point63.3 °C (145.9 °F; 336.4 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Isodurene or1,2,3,5-tetramethylbenzene is anorganic compound with the formula C6H2(CH3)4, classified as anaromatic hydrocarbon. It is a flammable colorless liquid which is nearly insoluble in water but soluble in organic solvents. It occurs naturally incoal tar. Isodurene is one of three isomers oftetramethylbenzene, the other two beingprehnitene (1,2,3,4-tetramethylbenzene) anddurene (1,2,4,5-tetramethylbenzene).[1]

Preparation

[edit]

Isoodurene can be prepared frommesitylene, which is converted tomesityl bromide. The latter reacts with magnesium to give the Grignard reagent, which can be alkylated withdimethyl sulfate:[2]

Industrially, isodurene can be isolated from thereformed fraction ofoil refineries. It may also be produced bymethylation of toluene, xylenes, andtrimethylbenzenes.[1]

References

[edit]
  1. ^abGriesbaum, 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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Saturated
aliphatic
hydrocarbons
Alkanes
CnH2n + 2
Linear alkanes
Branched alkanes
Cycloalkanes
Alkylcycloalkanes
Bicycloalkanes
Polycycloalkanes
Other
Unsaturated
aliphatic
hydrocarbons
Alkenes
CnH2n
Linear alkenes
Branched alkenes
Alkynes
CnH2n − 2
Linear alkynes
Branched alkynes
Cycloalkenes
Alkylcycloalkenes
Bicycloalkenes
Cycloalkynes
Dienes
Other
Aromatic
hydrocarbons
PAHs
Acenes
Other
Alkylbenzenes
C2-Benzenes
Xylenes
Other
C3-Benzenes
Trimethylbenzenes
Other
C4-Benzenes
Cymenes
Tetramethylbenzenes
Other
Other
Vinylbenzenes
Other
Other
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