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2H-isoindole
Sign in to saveIn organic chemistry and heterocyclic chemistry, isoindole consists of a benzene ring fused with pyrrole. The compound is an isomer of indole. Its reduced form is isoindoline. The parent isoindole is a rarely encountered in the technical literature, but substituted derivatives are useful commercially and occur naturally. Isoindoles units occur in phthalocyanines, an important family of dyes. Some alkaloids containing isoindole have been isolated and characterized.
Chemical data
- Formula
- C8H7N
- Molecular weight
- 117.15 g/mol
- IUPAC name
- 2H-isoindole
- SMILES
- C1=CC2=CNC=C2C=C1
- InChIKey
- VHMICKWLTGFITH-UHFFFAOYSA-N
- XLogP
- 2
- Polar surface area
- 15.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
~2 min read
Encyclopedic overview
5 sectionsContents
- Synthesis
- Structure and tautomerism of 2-H-isoindoles
- Isoindole-1,3-diones and related derivatives
- See also
- References
In organic chemistry and heterocyclic chemistry, isoindole consists of a benzene ring fused with pyrrole. The compound is an isomer of indole. Its reduced form is isoindoline. The parent isoindole is a rarely encountered in the technical literature, but substituted derivatives are useful commercially and occur naturally. Isoindoles units occur in phthalocyanines, an important family of dyes. Some alkaloids containing isoindole have been isolated and characterized.
==Synthesis== The parent isoindole was prepared by flash vacuum pyrolysis of an N-substituted isoindoline. N-Substituted isoindoles, which are easier to handle, can be prepared by dehydration of isoindoline-N-oxides. They also arise by myriad other methods, e.g., starting from xylylene dibromide (C6H4(CH2Br)2).
Excerpted from Wikipedia’s “2H-isoindole” article, available under the CC BY-SA 4.0 licence.