Isoindole

Isoindole

Chembox new
ImageFile=Isoindol.svg
ImageSize=150px
IUPACName=2"H"-Isoindole
OtherNames=
Section1= Chembox Identifiers
CASNo=270-68-8
PubChem=3013853
SMILES=C1=CC2=CNC=C2C=C1
Section2= Chembox Properties
Formula=C8H7N
MolarMass=117.15 g/mol
Appearance=
Density=
MeltingPt=
BoilingPt=
Solubility=
Section3= Chembox Hazards
MainHazards=
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Autoignition=

Isoindole in heterocyclic chemistry is a benzo fused pyrrole. [Heterocyclic chemistry T.L. Gilchrist ISBN 0852014220] 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:Fact|date=February 2008

:

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


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