Isatin

Isatin

Names
IUPAC name 1H-indole-2,3-dione
Identifiers
CAS Number	91-56-5 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:27539 Y
ChemSpider	6787 Y
DrugBank	DB02095 Y
ECHA InfoCard	100.001.889
KEGG	C11129 Y
PubChem CID	7054
InChI InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11) Y Key: JXDYKVIHCLTXOP-UHFFFAOYSA-N Y 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)
Hazards
EU classification (DSD)	Harmful (Xn)
R-phrases	R22 R36 R37 R38
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Isatin or 1H-indole-2,3-dione is an indole derivative. The compound was first obtained by Erdmann 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, such as Isatis tinctoria, Calanthe discolor and in Couroupita guianensis.

Schiff bases of isatin are investigated for their pharmaceutical properties.

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.

The classical methods for the synthesis of isatins are Sandmeyer’s method, the Stolle procedure, and Gassman procedure, all using aniline as substrate.