Isatin
From Wikipedia, the free encyclopedia
| Isatin | |
|---|---|
 |
|
| IUPAC name | 1H-indole-2,3-dione |
| Identifiers | |
| CAS number | [91-56-5] |
| SMILES | O=C1c2ccccc2NC1=O |
| InChI | 1/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11) |
| Properties | |
| Molecular formula | C8H5NO2 |
| Molar mass | 147.1308 g/mol |
| Appearance | Orange-red solid |
| Melting point |
200 °C, 473 K, 392 °F |
| Hazards | |
| EU classification | Harmful (Xn) |
| R-phrases | R22 R36 R37 R38 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Isatin or 1H-indole-2,3-dione is an indole derivative. The compound was first obtained by Erdman[1] and Laurent[2] in 1841 as a product from the oxidation of Indigo dye by nitric acid and chromic acids. The compound is found in many plants.
Schiff bases of Isatin are investigated for their pharmaceutical properties .[3]
It was observed that isatin forms a blue dye if it is mixed with sulfuric acid and crude benzene. The formation of the blue indophenin was long believed to be a reaction with benzene. Victor Meyer was able to isolate the substance resposible for this reaction from benzene. This new heterocyclic compound was thiophene.[4]
[edit] Preparation
Isatin is commercially available. It may be prepared from cyclicizing the condensation product of chloral hydrate, aniline and hydroxylamine in sulfuric acid:[5]
Isatins can be made from the corresponding indole in good yield by a mix of InCl3 and IBX in a acetonitrile-water solution at 80 °C.[6]
[edit] References
- ^ Otto Linné Erdmann (1840). "Untersuchungen über den Indigo". Journal für Praktische Chemie 19, (1): 321–362. doi:.
- ^ Auguste Laurent (1840). "Recherches sur l'indigo". Ann. chim. phys. 3, (3): 393–434.
- ^ Synthesis of 3,3´-[methylenebis(3,1-phenylenenitrilo)]bis[1,3-dihydro]-2H-indol-2-one as a novel bis-Schiff base A. A. Jarrahpour, D. Khalili Molbank 2005, M437 Online Article
- ^ Ward C. Sumpter (1944). "The Chemistry of Isatin". Chemical Reviews 34, (3): 393–434. doi:.
- ^ C. S. Marvel and G. S. Hiers (1941). "Isatin". Org. Synth.; Coll. Vol. 1: 327.
- ^ Yadav, J. S. (2007). "Indium(III) Chloride/2-Iodoxybenzoic Acid: A Novel Reagent System for the Conversion of Indoles to Isatins". Synthesis (5): 693–696. doi:.
[edit] Further reading
- Piyasena Hewawasam and Nicholas A. Meanwell (1994). "A general method for the synthesis of isatins". Tetrahedron Letters 35 (40): 7303–6. doi:.
