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Isobenzofuran

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Isobenzofuran
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name 2-Benzofuran
Other names 2-Oxa-2H-isoindene; Benzofuran
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H6O/c1-2-4-8-6-9-5-7(8)3-1/h1-6HKey: UXGVMFHEKMGWMA-UHFFFAOYSA-N
  • InChI=1/C8H6O/c1-2-4-8-6-9-5-7(8)3-1/h1-6HKey: UXGVMFHEKMGWMA-UHFFFAOYAR
SMILES
  • o2cc1ccccc1c2
Properties
Chemical formula C8H6O
Molar mass 118.13 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

Isobenzofuran is a bicyclic heterocycle consisting of fused cyclohexa-1,3-diene and furan rings. It is isomeric with benzofuran.

Isobenzofuran is highly reactive and rapidly polymerizes; however, it has been identified and prepared by thermolysis of suitable precursors and trapped at low temperature.

Though isobenzofuran itself is not stable, it is the parent of related stable compounds with more complex structures, such as the hindered analogue 1,3-diphenylisobenzofuran.

References

  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 218. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. Fieser, L. F.; Haddadin, M. J. (1964). "Isobenzofuran, a Transient Intermediate". Journal of the American Chemical Society. 86 (10): 2081–2082. doi:10.1021/ja01064a044.
  3. Wege, D. (1971). "Isolation of Isobenzofuran". Tetrahedron Letters. 12 (25): 2337–2338. doi:10.1016/S0040-4039(01)96856-X.
  4. Joule, J. A.; Mills, K.; Smith, G. F. (1995). Heterocyclic Chemistry (3rd ed.). CRC Press. pp. 364–365. ISBN 978-0748740697.
Simple aromatic rings
1 ring
Three-membered
Five-membered
Six-membered
Seven-membered
Nine-membered
18-membered
2 rings
Five + Five
Five + Six
Six + Six
Five + Seven
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