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indene

 
Dictionary: in·dene   (ĭn'dēn') pronunciation
 
n.

A colorless organic liquid, C9H8, obtained from coal tar and used in preparing synthetic resins.

[IND(OLE) + –ENE.]


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A colourless flammable hydrocarbon, C9H8; r.d. 0.996; m.p. –1.8°C; b.p. 182.6°C. Indene is an aromatic hydrocarbon with a five-membered ring fused to a benzene ring. It is present in coal tar and is used as a solvent and raw material for making other organic compounds.



 
WordNet: indene
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Note: click on a word meaning below to see its connections and related words.

The noun has one meaning:

Meaning #1: a colorless liquid hydrocarbon extracted from petroleum or coal tar and used in making synthetic resins


 
Wikipedia: Indene
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Indene
IUPAC name
Other names benzocyclopentadiene
Identifiers
CAS number [95-13-6]
PubChem 7219
SMILES
Properties
Molecular formula C9H8
Molar mass 116.16
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox references

Indene is a flammable polycyclic hydrocarbon with chemical formula C9H8. It is composed of a benzene ring fused with a cyclopentene ring. This aromatic liquid is colorless although samples often are pale yellow. The principal industrial use of indene is in the production of indene/cumarone thermoplastic resins.

Contents

Isolation

Indene occurs naturally in coal-tar fractions boiling around 175-185 °C. It can be obtained by heating this fraction with sodium to precipitate solid "sodio-indene." This step exploits indenes weak acidity evidenced by its deprotonation by sodium to give the indenyl derivative. The sodio-indene is converted back to indene by steam distillation.[1]

Reactivity

Indene readily polymerises. Oxidation of indene with acid dichromate yields homophthalic acid (o-carboxylphenylacetic acid). It condenses with ethyl oxalate in the presence of sodium ethoxide to form indene-oxalic ester, and with aldehydes or ketones in the presence of alkali to form benzofulvenes. The latter are highly coloured. An indene is also a precursor to the indenyl anion, a ligand in organometallic chemistry with some notability due to the indenyl effect.

See also

References

  1. ^ Gerd Collin, Rolf Mildenberg, Mechthild Zander, Hartmut Höke, William McKillip, Werner Freitag, Wolfgang Imöhl “Resins, Synthetic” Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2000.

See also

  • W. v. Miller, Rohde (1890). "Zur Synthese von Indenderivaten". Berichte der deutschen chemischen Gesellschaft 23 (2): 1881–1886. doi:10.1002/cber.18900230227. 
  • W. v. Miller, Rohde (1890). "Zur Synthese von Indenderivaten". Berichte der deutschen chemischen Gesellschaft 23 (2): 1887–1902. doi:10.1002/cber.18900230228. 
  • Finar, I. L. (1985). Organic Chemistry. Longman Scientific & Technical. ISBN 0582442575. 



 
 
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Dictionary. The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2007. Published by Houghton Mifflin Company. All rights reserved.  Read more
Chemistry Dictionary. A Dictionary of Chemistry. Sixth Edition. Copyright © Market House Books Ltd, 2008. All rights reserved.  Read more
WordNet. WordNet 1.7.1 Copyright © 2001 by Princeton University. All rights reserved.  Read more
Wikipedia. This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Indene" Read more