Isobenzofuran

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

Isobenzofuran
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
2-Benzofuran[1]
Other names
2-Oxa-2H-isoindene; Benzo[c]furan
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C8H6O/c1-2-4-8-6-9-5-7(8)3-1/h1-6H checkY
    Key: UXGVMFHEKMGWMA-UHFFFAOYSA-N checkY
  • InChI=1/C8H6O/c1-2-4-8-6-9-5-7(8)3-1/h1-6H
    Key: UXGVMFHEKMGWMA-UHFFFAOYAR
  • o2cc1ccccc1c2
Properties
C8H6O
Molar mass 118.13 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Isobenzofuran is highly reactive and rapidly polymerizes; however, it has been identified[2] and prepared by thermolysis of suitable precursors and trapped at low temperature.[3]

Though isobenzofuran itself is not stable, it is the parent of related stable compounds with more complex structures, [4] 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.
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