Isatin

Isatin

Chembox new
ImageFile = Instatin.png ImageSize =
IUPACName = 1H-indole-2,3-dione
OtherNames =
Section1 = Chembox Identifiers
CASNo = 91-56-5
PubChem =
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)
Section2 = Chembox Properties
Formula = C8H5NO2
MolarMass = 147.1308 g/mol
Appearance = Orange-red solid
Density =
MeltingPtC = 200
BoilingPt =
Solubility =
Section3 = Chembox Hazards
EUClass = Harmful (Xn)
MainHazards =
FlashPt =
Autoignition =
RPhrases = R22 R36 R37 R38

Isatin or 1H-indole-2,3-dione is an indole derivative. The compound was first obtained by Erdman [cite journal
author= Otto Linné Erdmann
title = Untersuchungen über den Indigo
journal = Journal für Praktische Chemie
year = 1840
volume = 19,
issue = 1
pages = 321–362
doi = 10.1002/prac.18400190161] and Laurent [cite journal
author= Auguste Laurent
title = Recherches sur l'indigo
journal = Ann. chim. phys.
year = 1840
volume = 3,
issue = 3
pages = 393–434
url = http://gallica.bnf.fr/ark:/12148/bpt6k347443/f370.table] 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 . [ "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 [http://www.mdpi.net/molbank/molbank2005/m437.htm Online Article] ]

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 responsible for this reaction from benzene. This new heterocyclic compound was thiophene. [cite journal
author= Ward C. Sumpter
title = The Chemistry of Isatin
journal = Chemical Reviews
year = 1944
volume = 34,
issue = 3
pages = 393–434
doi = 10.1021/cr60109a003]

Preparation

Isatin is commercially available. It may be prepared from cyclicizing the condensation product of chloral hydrate, aniline and hydroxylamine in sulfuric acid: [OrgSynth | title = Isatin | author = C. S. Marvel and G. S. Hiers | collvol = 1 | collvolpages = 327 | year = 1941 | prep = cv1p0327]

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. [cite journal
author= Yadav, J. S.
title = Indium(III) Chloride/2-Iodoxybenzoic Acid: A Novel Reagent System for the Conversion of Indoles to Isatins
journal = Synthesis
year = 2007
volume =2007
issue = 5
pages = 693–696
doi = 10.1055/s-2007-965930]

References

Further reading

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Look at other dictionaries:

  • Isatīn — (oxydirter Indig C16H5NO4 = (C16H5NO2 + 2O), Zersetzungsproduct des Indigblaues, s.u. Indig 2) D) e); schöne durchsichtige rhombische Prismen von hellrother Farbe, ohne Geruch, schwer löslich in kaltem Wasser, leichter löslich in heißem Wasser u …   Pierer's Universal-Lexikon

  • Isatin — I sa*tin, n. [See {Isatis}.] (Chem.) An orange red crystalline substance, {C8H5NO2}, obtained by the oxidation of indigo blue. It is also produced from certain derivatives of benzoic acid, and is one important source of artificial indigo.… …   The Collaborative International Dictionary of English

  • Isatīn — C8H5NO2 oder #, das Laktim der Orthoamidophenylglyoxylsäure (Isatinsäure), aus der es beim Erwärmen entsteht, wird aus Orthonitrophenylpropiolsäure bei Einwirkung von Alkalien und bei Behandlung von Indigo mit Salpetersäure, auch bei Oxydation… …   Meyers Großes Konversations-Lexikon

  • isatin — [ī′sə tin] n. [< L isatis, variety of herb (< Gr isatis, woad) + IN1] a reddish orange, crystalline compound, C8H5NO2, produced by the oxidation of indigo and used in making dyes …   English World dictionary

  • Isatin — Strukturformel Allgemeines Name Isatin Andere Namen 2,3 Indolindion …   Deutsch Wikipedia

  • Isatin — Isa|tin 〈n. 11; unz.; Chem.〉 in gelbroten Prismen kristallisierende, organ. chem. Verbindung zur Herstellung von indigoartigen Farbstoffen [<grch. isatis, Name einer Pflanzengattung] * * * I|sa|tin [nlat. Isatis tinctoria = Färberwaid (Bot.);… …   Universal-Lexikon

  • isatin — izatinas statusas T sritis chemija formulė NC₈H₅(=O)₂ atitikmenys: angl. isatin rus. изатин ryšiai: sinonimas – 2,3 indolindionas …   Chemijos terminų aiškinamasis žodynas

  • isatin — /uy seuh tin/, n. Chem. a yellowish red or orange, crystalline, water soluble solid, C8H5NO2, used chiefly in the synthesis of vat dyes. [1835 45; < Gk isát(is) woad + IN2] * * * …   Universalium

  • isatin — noun The indole derivative 1H indole 2,3 dione that is used in the synthesis of dyes …   Wiktionary

  • isatin — isa·tin ī sət ən n an orange red crystalline compound C8H5NO2 obtained esp. by oxidation of indigo or by various syntheses and used as a reagent * * * isa·tin (iґsə tin) a crystalline compound, C8H5O2N, in the form of yellowish red crystals …   Medical dictionary

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