|Jmol-3D images||Image 1|
|Molar mass||117.15 g/mol|
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Isoindole in heterocyclic chemistry is a benzo-fused pyrrole. The compound is an isomer of indole and its reduced form is an isoindoline. Isoindoles are building blocks for phthalocyanines which are relevant as dyes. Some alkaloids containing isoindole have been isolated and characterized.
In solution, the 2H-isoindole tautomer is the predominant form and therefore the compound resembles a pyrrole more than a simple imine. The degree to which the 2H predominates depends on the solvent, and can vary with the substituent in substituted isoindoles.
The commercially important phthalimide is an isoindole-1,3-dione with two carbonyl groups attached to the heterocyclic ring. There are a variety of natural products and pharmaceutical drugs based on phthalimide.
- Gilchrist, T. L. (1987). Heterocyclic Chemistry. Longman. ISBN 0-582-01422-0.
- See for example: Zhang, X.; Ye, W.; Zhao, S.; Che, C. T. (2004). "Isoquinoline and isoindole alkaloids from Menispermum dauricum". Phytochemistry 65 (7): 929–932. doi:10.1016/j.phytochem.2003.12.004. PMID 15081297.
- Alan R. Katritzky, Christopher A. Ramsden, J. Joule, Viktor V. Zhdankin (2010). Handbook of Heterocyclic Chemistry. Elsevier. p. 133.
- John A. Joule, Keith Mills (2010). Heterocyclic Chemistry. John Wiley & Sons. p. 447.