Isoindole
Appearance
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Names | |
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IUPAC name
2H-Isoindole
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Identifiers | |
3D model (JSmol)
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ChEBI | |
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PubChem CID
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CompTox Dashboard (EPA)
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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).
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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]
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
- Isoindene with nitrogen replaced by a methylene group.
References
- ^ Gilchrist, T. L. (1987). Heterocyclic Chemistry. Longman. ISBN 0-582-01422-0.