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Isoindole information


Isoindole
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
2H-Isoindole[1]
Identifiers
CAS Number
  • 270-68-8 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:33179 checkY
ChemSpider
  • 2282425 checkY
PubChem CID
  • 3013853
UNII
  • PR6T8TL5NT checkY
CompTox Dashboard (EPA)
  • DTXSID40181488 Edit this at Wikidata
InChI
  • InChI=1S/C8H7N/c1-2-4-8-6-9-5-7(8)3-1/h1-6,9H checkY
    Key: VHMICKWLTGFITH-UHFFFAOYSA-N checkY
  • InChI=1/C8H7N/c1-2-4-8-6-9-5-7(8)3-1/h1-6,9H
    Key: VHMICKWLTGFITH-UHFFFAOYAW
SMILES
  • c1cccc2c1c[nH]c2
Properties
Chemical formula
C8H7N
Molar mass 117.15 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

In organic chemistry and heterocyclic chemistry, isoindole consists of a benzene ring fused with pyrrole.[2] 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.[3][4]

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 213. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ Gilchrist, T. L. (1987). Heterocyclic Chemistry. Longman. ISBN 0-582-01422-0.
  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. ^ See for example: Zhang, X.; Ye, W.; Zhao, S.; Che, C. T. (2004). "Isoquinoline and isoindole alkaloids from Menispermum dauricum". Phytochemistry. 65 (7): 929–932. doi:10.1016/j.phytochem.2003.12.004. PMID 15081297.

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Isoindole

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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...

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Phthalocyanine

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interest in chemical dyes and photoelectricity. It is composed of four isoindole units linked by a ring of nitrogen atoms. (C8H4N2)4H2 = H2Pc has a two-dimensional...

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Heterocyclic compound

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benzo-fused unsaturated nitrogen heterocycles, pyrrole provides indole or isoindole depending on the orientation. The pyridine analog is quinoline or isoquinoline...

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Tautomer

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example, 1H- and 3H-imidazole; 1H-, 2H- and 4H- 1,2,4-triazole; 1H- and 2H- isoindole. Ring–chain tautomers occur when the movement of the proton is accompanied...

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Simple aromatic ring

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of simple aromatic rings Furan Benzofuran Isobenzofuran Pyrrole Indole Isoindole Thiophene Benzothiophene Benzo[c]thiophene Imidazole Benzimidazole Purine...

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Isoindoline

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Isoindoline Isoindoline Speck Klaus; Magauer Thomas "The chemistry of isoindole natural products" Beilstein journal of organic chemistry 2013, vol. 9...

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Annulation

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Benzopyrene Pyrene Quinoline Pyridine Isoquinoline Chromene Pyran Isochromene Indole Pyrrole Isoindole Benzofuran Furan Isobenzofuran Benzimidazole Imidazole...

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Imine

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Formation of (3aS,7aS)-2[2-(3,4-Dimethoxyphenyl)-ethyl]-1,3-dioxo-octahydro-isoindole-3a-Carboxylic Acid Methyl Ester". Organic Syntheses. 84: 306. doi:10.15227/orgsyn...

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C8H7N

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mass: 117.0578 u) may refer to: Benzyl cyanide (BnCN) Indole Indolizine Isoindole This set index page lists chemical structure articles associated with...

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Indole

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hydrogenation of the imine subunit. Indole-3-butyric acid Indole test Isoindole Isoindoline Skatole (3-methylindole) International Union of Pure and Applied...

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Nitrene

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this C–H insertion involving an oxime, acetic anhydride leading to an isoindole: Nitrene cycloaddition. With alkenes, nitrenes react to form aziridines...

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Phthalimide

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Phthalimide Names Preferred IUPAC name 1H-Isoindole-1,3(2H)-dione Other names 1,3-dioxoisoindoline Phthalimidoyl (deprotonated) Identifiers CAS Number...

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Phthalazine

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yields a chlorphthalazine, which with zinc and hydrochloric acid gives isoindole (C8H7N), and with tin and hydrochloric acid, phthalimidine (C8H7ON), the...

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Pomalidomide

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faeces (15%) Identifiers IUPAC name 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione CAS Number 19171-19-8 Y PubChem CID 134780 IUPHAR/BPS 7348 DrugBank...

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Pigment yellow 139

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Pigment yellow 139 Names Preferred IUPAC name 5,5′-(1H-Isoindole-1,3(2H)-diylidene)di(1,3-diazinane-2,4,6-trione) Other names Lithol, Fast Yellow 1840...

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Lurasidone

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2-Benzisothiazol-3-yl)-1-piperazinyl]methyl]cyclohexyl]methyl]hexahydro-4,7-methano-1H-isoindole-1,3(2H)-dione". PubChem. U.S. National Library of Medicine. Archived from...

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Tetramethrin

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Tetramethrin is a potent synthetic insecticide in the pyrethroid family. It is a white crystalline solid with a melting point of 65–80 °C. The commercial...

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Mazindol

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Anorectic Drugs: 145–64. US granted 3597445, Houlihan WJ, Eberle MK, "1H-Isoindole Intermediates", issued 3 August 1971, assigned to Sandoz AG  Grover N...

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Captan

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name (3aR,7aS)-2-[(Trichloromethyl)sulfanyl]-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione Identifiers CAS Number 133-06-2 Y 3D model (JSmol) Interactive...

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Imide

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Maleimide Pyrrole-2,5-dione 10935 Maleic acid 3 Glutarimide Piperidine-2,6-dione 70726 Glutaric acid 6 Phthalimide Isoindole-1,3-dione 6809 Phthalic acid...

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Folpet

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Folpet Names Preferred IUPAC name 2-[(Tricloromethyl)sulfanyl]-1H-isoindole-1,3(2H)-dione Other names N-(Trichloromethylthio)phthalimide, Orthophaltan...

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Chrome yellow

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replaced with organic pigments such as arylides (Pigment Yellow 65) and isoindoles (PY 110). Vincent van Gogh used chrome yellow in many of his paintings...

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Isoindene

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hydrocarbon with chemical formula C9H8. It is composed of a cyclohexadiene ring fused with a cyclopentadiene ring. Indene Isoindole Isoindenone v t e...

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Muironolide A

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forming the lactonic ring, with an amino acid residue, which forms the isoindole ring present in the molecule and successive enzymatic transformations...

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Photodynamic therapy

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PC derivative. They have an additional benzene ring attached to each isoindole sub-unit on the periphery of the PC structure. Subsequently, NCs absorb...

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Captafol

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(3aR,7aS)-2-[(1,1,2,2-Tetrachloroethyl)sulfanyl]-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione Other names cis-Captafol; Merpafol; Crisfolatan; Sulfonimide;...

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Cyclohexylthiophthalimide

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cyclohexylthiophthalimide Names Preferred IUPAC name 2-(Cyclohexylsulfanyl)-1H-isoindole-1,3(2H)-dione Identifiers CAS Number 17796-82-6 Y 3D model (JSmol) Interactive...

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