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Isoindole

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Title: Isoindole  
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Subject: Simple aromatic ring, Isoindene, Annulation, C8H7N, Indole
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Isoindole

Isoindole
Identifiers
CAS number 270-68-8 YesY
PubChem 3013853
ChemSpider 2282425 YesY
ChEBI CHEBI:33179 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H7N
Molar mass 117.15 g/mol
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Isoindole in heterocyclic chemistry is a benzo-fused pyrrole.[1] 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.[2]

Tautomerism

In solution, the 2H-isoindole tautomer is the predominant form and therefore the compound resembles a pyrrole more than a simple imine.[3] The degree to which the 2H predominates depends on the solvent, and can vary with the substituent in substituted isoindoles.[4]

Isoindole-1,3-diones

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.

See also

  • Isoindene with nitrogen replaced by a methylene group.

References

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