Isatin

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Isatin
Isatin.png
Names
IUPAC name
1H-indole-2,3-dione
Identifiers
91-56-5 YesY
ChEBI CHEBI:27539 YesY
ChEMBL ChEMBL326294 YesY
ChemSpider 6787 YesY
DrugBank DB02095 YesY
Jmol-3D images Image
KEGG C11129 YesY
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)
 YesY verify (what isYesY/N?)
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[edit]

References[edit]

  1. ^ Erdmann, O. L. (1840). "Untersuchungen über den Indigo". Journal für Praktische Chemie 19 (1): 321–362. doi:10.1002/prac.18400190161. 
  2. ^ Laurent, A. (1840). "Recherches sur l'indigo". Annales de Chimie et de Physique 3 (3): 393–434. 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ Sumpter, W. C. (1944). "The Chemistry of Isatin". Chemical Reviews 34 (3): 393–434. doi:10.1021/cr60109a003. 

Further reading[edit]