Isoindole

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Isoindole
IUPAC name	2H-Isoindole
Identifiers
CAS number	[270-68-8]
PubChem	3013853
SMILES	C1=CC2=CNC=C2C=C1
Properties
Molecular formula	C8H7N
Molar mass	117.15 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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.

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

[edit] 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.

[edit] See also

• Isoindene with nitrogen replaced by a methylene group.

[edit] References