Isoindole

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title: "Isoindole" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["isoindoles", "simple-aromatic-rings"] topic_path: "general/isoindoles" source: "https://en.wikipedia.org/wiki/Isoindole" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| verifiedrevid = 443885075 | ImageFile = Isoindol.svg | ImageClass = skin-invert-image | ImageSize = 150px | ImageName = Skeletal formula | ImageFile1 = Isoindole-3D-balls-2.png | ImageName1 = Ball-and-stick model | PIN=2H-Isoindole | OtherNames= |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 2282425 | InChI = 1/C8H7N/c1-2-4-8-6-9-5-7(8)3-1/h1-6,9H | InChIKey = VHMICKWLTGFITH-UHFFFAOYAW | StdInChI_Ref = | StdInChI = 1S/C8H7N/c1-2-4-8-6-9-5-7(8)3-1/h1-6,9H | StdInChIKey_Ref = | StdInChIKey = VHMICKWLTGFITH-UHFFFAOYSA-N | CASNo_Ref = | CASNo=270-68-8 | UNII_Ref = | UNII = PR6T8TL5NT | PubChem=3013853 | ChEBI_Ref = | ChEBI = 33179 | SMILES = c1cccc2c1c[nH]c2 |Section2={{Chembox Properties | Formula=C8H7N | MolarMass=117.15 g/mol | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt =

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.See for example: {{Cite journal | last1 = Zhang | first1 = X. | last2 = Ye | first2 = W. | last3 = Zhao | first3 = S. | last4 = Che | first4 = C. T. | title = Isoquinoline and isoindole alkaloids from Menispermum dauricum | doi = 10.1016/j.phytochem.2003.12.004 | journal = Phytochemistry | volume = 65 | issue = 7 | pages = 929–932 | year = 2004 | pmid = 15081297 | pmc =

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).

Structure and tautomerism of 2-H-isoindoles

Unlike indole, isoindoles exhibit noticeable alternation in the C-C bond lengths, which is consistent with their description as pyrrole derivatives fused to a butadiene.

In solution, the 2H-isoindole tautomer predominates. It resembles a pyrrole more than a simple imine. The degree to which the 2H predominates depends on the solvent, and can vary with the substituent in substituted isoindoles.

:[[File:Isoindoletautomerism.svg|class=skin-invert-image|thumb|left|400px|2H-Isoindole (right) is the predominant tautomer relative to 1H-isoindole (left)]]

N-Substituted isoindoles do not engage is tautomerism and are therefore simpler to study.

Isoindole-1,3-diones and related derivatives

The commercially important phthalimide is an isoindole-1,3-dione with two carbonyl groups attached to the heterocyclic ring. File:PY139.svg|Pigment yellow 139, a common high performance pigment. File:PY185.svg|Pigment yellow 185, a common high performance pigment. File:Copper phthalocyanine.svg|Copper phthalocyanine, one of the most pervasive synthetic pigments.

References

References

  1. [[International Union of Pure and Applied Chemistry]]. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013". [[Royal Society of Chemistry.
  2. Gilchrist, T. L.. (1987). "Heterocyclic Chemistry". Longman.
  3. Heugebaert, Thomas S. A.; Roman, Bart I.; Stevens, Christian V. "Synthesis of isoindoles and related iso-condensed heteroaromatic pyrroles" Chemical Society Reviews 2012, volume 41, pp. 5626-5640. {{doi. 10.1039/c2cs35093a
  4. R. Bonnett and R. F. C. Brown "Isoindole" J. Chem. Soc., Chem. Commun., 1972, 393-395. {{doi. 10.1039/C39720000393
  5. (2010). "Handbook of Heterocyclic Chemistry". Elsevier.
  6. (2010). "Heterocyclic Chemistry". John Wiley & Sons.

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isoindolessimple-aromatic-rings