Misplaced Pages

Isatin

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

This is an old revision of this page, as edited by Beetstra (talk | contribs) at 14:35, 9 August 2011 (Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEBI').). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 14:35, 9 August 2011 by Beetstra (talk | contribs) (Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEBI').)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
Isatin
Names
IUPAC name 1H-indole-2,3-dione
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.889 Edit this at Wikidata
KEGG
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)Key: JXDYKVIHCLTXOP-UHFFFAOYSA-N
  • InChI=1/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
SMILES
  • O=C2c1ccccc1NC2=O
Properties
Chemical formula C8H5NO2
Molar mass 147.1308 g/mol
Appearance Orange-red solid
Melting point 200 °C (392 °F; 473 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Isatin or 1H-indole-2,3-dione is an indole derivative. The compound was first obtained by Erdman and Laurent 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 .

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 responsible for this reaction from benzene. This new heterocyclic compound was thiophene.

Preparation

Isatin is commercially available. It may be prepared from cyclicizing the condensation product of chloral hydrate, aniline and hydroxylamine in sulfuric acid:. This reaction is called the Sandmeyer isonitrosoacetanilide Isatin Synthesis and discovered by Traugott Sandmeyer in 1919.

Another classic reaction, the Sandmeyer diphenylurea isatin synthesis (Sandmeyer 1903), starts from diphenylthiourea, potassium cyanide, and lead carbonate

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.

References

  1. Otto Linné Erdmann (1840). "Untersuchungen über den Indigo". Journal für Praktische Chemie. 19 (1): 321–362. doi:10.1002/prac.18400190161.
  2. Auguste Laurent (1840). "Recherches sur l'indigo". Ann. Chim. Phys. 3 (3): 393–434.
  3. Synthesis of 3,3´-bis-2H-indol-2-one as a novel bis-Schiff base A. A. Jarrahpour, D. Khalili Molbank 2005, M437 Online Article
  4. Ward C. Sumpter (1944). "The Chemistry of Isatin". Chemical Reviews. 34 (3): 393–434. doi:10.1021/cr60109a003.
  5. C. S. Marvel and G. S. Hiers (1941). "Isatin". Organic Syntheses; Collected Volumes, vol. 1, p. 327.
  6. Sandmeyer, T.: Über Isonitrosoacetanilide und deren Kondensation zu Isatinen, in: Helv. Chim. Acta 1919, 2 (1), 234–242; doi:10.1002/hlca.19190020125.
  7. Isatin synthesis @ drugfuture.com
  8. Yadav, J. S.; Reddy, B.; Reddy, Ch.; Krishna, A. (2007). "Indium(III) Chloride/2-Iodoxybenzoic Acid: A Novel Reagent System for the Conversion of Indoles to Isatins". Synthesis. 2007 (5): 693–696. doi:10.1055/s-2007-965930.

Further reading

Category:
Isatin Add topic