Isoindole

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Structural formula
Structural formula of isoindole
General
Surname Isoindole
other names
  • 2 H -isoindole ( IUPAC )
  • Benzo [ c ] pyrrole
Molecular formula C 8 H 7 N
External identifiers / databases
CAS number 270-68-8
PubChem 3013853
Wikidata Q760735
properties
Molar mass 117.15 g mol −1
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Isoindole is a chemical compound from the group of bicyclic heteroaromatics and is the nitrogen analogue of isobenzofuran . It is made up of a pyrrole ring and a fused benzene ring. It is isomeric to indole . The compound forms the basic structure of other chemical compounds such as phthalocyanines .

Appearance and properties

Isoindole can be prepared by vacuum - pyrolysis or a retro Diels-Alder reaction are obtained.

1,2,3,4-tetrahydronaphthalene-1,4-imines → 2H-isoindoles + 1H-isoindoles.svg

It is unstable and converts at temperatures above −40 ° C. Depending on the conditions, the compound is in two tautomeric forms (2 H -isoindole and 1 H -isoindole / 1 H -isoindolenine) or an equilibrium of the two forms, the predominant form generally depending on the substituent in the case of substituted isoindoles.

2 H -isoindole (right) is the predominant tautomer compared to 1 H -isoindole (left)

Individual evidence

  1. This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ^ Karl M Kadish, Kevin Smith, Roger Guilard: Handbook of Porphyrin Science: Synthesis and structural studies . World Scientific, 2010, ISBN 981-4322-35-0 , pp. 38 ( limited preview in Google Book search).