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Indene

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Indene Basic information
  • Product Name:Indene
  • CAS:95-13-6
  • MF:C9H8
  • MW:116.16
  • EINECS:202-393-6
  • Mol File:95-13-6.mol
Indene Chemical Properties
  • Melting point:−5-−3 °C(lit.)
  • Boiling point:181-182 °C(lit.)
  • Density 0.996 g/mL at 25 °C(lit.)
  • vapor pressure 1.7 hPa (20 °C)
  • refractive index n20/D 1.595(lit.)
  • Flash point:138 °F
  • storage temp. 2-8°C
  • solubility organic solvents: miscible
  • pka20(at 25℃)
  • form Crystalline Powder
  • color White to pale yellow
  • Odor Threshold0.0038ppm
  • Water Solubility INSOLUBLE
  • Sensitive Light Sensitive
  • Merck 14,4939
  • BRN 635873
  • Stability:Stable, but air and light sensitive; may polymerize upon exposure to light. Typically contains aroung 80 - 100 ppm of p-tert-butylcatechol as inhibitor. Refrigerate. Flammable. Incompatible with strong oxidizing agents.
  • InChIKeyYBYIRNPNPLQARY-UHFFFAOYSA-N
  • CAS DataBase Reference95-13-6(CAS DataBase Reference)
  • NIST Chemistry ReferenceIndene(95-13-6)
  • EPA Substance Registry SystemIndene (95-13-6)
Safety Information
MSDS
Indene Usage And Synthesis
  • DescriptionIndene (also called 1H-Indene, C9H8) is a flammable polycyclic hydrocarbon. It is a colorless and aromatic smelling liquid. It is used in the synthesis of new C60 derivative (indene-C60 Bisadduct) and to prepare polyindene by the controlled cationic polymerization initiated with cumyl methyl ether/TiCl4 in CH2Cl2.  Polyindene is further used to synthesize polyolefins. Indene is also used in the synthesis of istatins, in the production of indene/cumarone thermoplastic resins, and in the production of hydrocarbon resins. These industrial resins, also called indene-coumarone resins, are mainly consumed by the paints & coatings, rubber, and construction industries.
    It should be stored in a cool place. The container should be kept tightly closed in a dry and well-ventilated place. Containers which areopened must be carefully resealed and kept upright to prevent leakage. Indene is incompatible with strong oxidizing agents. Recommended storage temperature is 2 - 8°C. Indene is sensitive to light.
  • References[1] https://en.wikipedia.org/wiki/Indene
    [2] https://www.alfa.com/de/catalog/L12665/
    [3] Stephen F. Hahn, Marc A. Hillmyer (2003) High glass transition temperature polyolefins obtained by the catalytic hydrogenation of polyindene, 36, 71-76.
  • Chemical PropertiesYellow green clear liquid
  • UsesPreparation of coumarone-indene resins, intermediate.
  • UsesPreparation of coumarone-indene resins
  • Definitionindene: A colourless flammable hydrocarbon,C9H8; r.d. 0.996; m.p.–1.8°C; b.p. 182.6°C. Indene is anaromatic hydrocarbon with a five-memberedring fused to a benzenering. It is present in coal tar and isused as a solvent and raw materialfor making other organic compounds.
  • Synthesis Reference(s)Tetrahedron Letters, 18, p. 49, 1977 DOI: 10.1016/S0040-4039(01)92547-X
  • General DescriptionA colorless liquid derived from coal tar. Fp: -2°C; bp:182°C. Density 0.997 g cm-3. Insoluble in water but soluble in organic solvents.
  • Reactivity ProfileIndene is combustible (flash point between 140°F and 200°F). Polymerizes and oxidizes on standing in the air. This reaction is accelerated by heating, acids, and catalysts, including peroxides. Has exploded during nitration with a mixture of H2SO4 and HNO3.
  • HazardToxic by inhalation.
  • Health HazardIndene is expected to be an irritant of the mucous membranes.
  • Purification MethodsShake indene with 6M HCl for 24hours (to remove basic nitrogenous material), then reflux it with 40% NaOH for 2hours (to remove benzonitrile). Fractionally distil, then fractionally crystallise it by partial freezing. The higher-melting portion is converted to its sodium salt by adding a quarter of its weight of sodamide under nitrogen and stirring for 3hours at 120o. Unreacted organic material is distilled off at 120o/1mm. The sodium salts are hydrolysed with water, and the organic fraction is separated by steam disillation, followed by fractional distillation. Before use, the distillate is passed, under nitrogen, through a column of activated silica gel. It turns yellow in air as it readily oxidizes and polymerises. [Russell J Am Chem Soc 78 1041 1956, Beilstein 5 IV 1532.]
Indene Preparation Products And Raw materials
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