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Isoindole

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Isoindole
Skeletal formula
Ball-and-stick model
Names
IUPAC name
2H-Isoindole
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C8H7N/c1-2-4-8-6-9-5-7(8)3-1/h1-6,9H checkY
    Key: VHMICKWLTGFITH-UHFFFAOYSA-N checkY
  • InChI=1/C8H7N/c1-2-4-8-6-9-5-7(8)3-1/h1-6,9H
    Key: VHMICKWLTGFITH-UHFFFAOYAW
  • c1cccc2c1cnc2
Properties
C8H7N
Molar mass 117.15 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Isoindole in heterocyclic chemistry is a benzo-fused pyrrole.[1] The compound is an isomer of indole and its reduced form is an isoindoline.

In solution its tautomer without full aromaticity over the whole ring system is predominant:[citation needed]

Isoindole tautomerism

and therefore the compound resembles a pyrrole more than a simple imine. Isoindoles are building blocks for phthalocyanines which are relevant as dyes

Isoindole-1,3-diones

The commercially important phthalimide is an isoindole-1,3-dione with two carbonyl groups attached to the heterocyclic ring. Thalidomide is an infamous drug based on this framework.

See also

References

  1. ^ Gilchrist, T. L. (1987). Heterocyclic Chemistry. Longman. ISBN 0-582-01422-0.
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