Isatin
 | |
| Names | |
|---|---|
| IUPAC name
1H-indole-2,3-dione | |
| Identifiers | |
91-56-5  | |
| ChEBI | CHEBI:27539 |
| ChEMBL | ChEMBL326294 |
| ChemSpider | 6787 |
| DrugBank | DB02095 |
| |
| Jmol-3D images | Image |
| KEGG | C11129 |
| PubChem | 7054 |
| |
| Properties | |
| C8H5NO2 | |
| Molar mass | 147.1308 g/mol |
| Appearance | Orange-red solid |
| Melting point | 200 °C (392 °F; 473 K) |
| Hazards | |
| EU classification | Harmful (Xn) |
| R-phrases | R22 R36 R37 R38 |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
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| Infobox references | |
Isatin or 1H-indole-2,3-dione is an indole derivative. The compound was first obtained by Erdmann[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, such as Isatis tinctoria, Calanthe discolor and in Couroupita guianensis.[3]
Schiff bases of isatin are investigated for their pharmaceutical properties.[4]
Isatin forms a blue dye (indophenin) if it is mixed with sulfuric acid and crude benzene. The formation of the indophenin was long believed to be a reaction with benzene. Victor Meyer was able to isolate the substance responsible for this reaction from crude benzene. This new heterocyclic compound was thiophene.[5]
See also
References
- ↑ Erdmann, O. L. (1840). "Untersuchungen über den Indigo". Journal für Praktische Chemie 19 (1): 321–362. doi:10.1002/prac.18400190161.
- ↑ Laurent, A. (1840). "Recherches sur l'indigo". Annales de Chimie et de Physique 3 (3): 393–434.
- ↑ da Silva, J. F. M.; Garden, S. J.; Pinto, A. C. (2001). "The Chemistry of Isatins: a Review from 1975 to 1999" (PDF). Journal of the Brazilian Chemical Society 12 (3): 273–324. doi:10.1590/S0103-50532001000300002.
- ↑ Jarrahpour, A. A.; Khalili, D. (2005). "Synthesis of 3,3´-[methylenebis(3,1-phenylenenitrilo)]bis[1,3-dihydro]-2H-indol-2-one as a Novel bis-Schiff Base" (PDF). Molbank 2005 (4): M437. doi:10.3390/M437.
- ↑ Sumpter, W. C. (1944). "The Chemistry of Isatin". Chemical Reviews 34 (3): 393–434. doi:10.1021/cr60109a003.
Further reading
- Hewawasam, P.; Meanwell, N. A. (1994). "A General Method for the Synthesis of Isatins". Tetrahedron Letters 35 (40): 7303–7306. doi:10.1016/0040-4039(94)85299-5.