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Merck
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Documenti

114618

Sigma-Aldrich

Isatin

97%

Sinonimo/i:

2,3-Diketoindoline, 2,3-Dioxo-2,3-dihydroindole, 2,3-Dioxoindoline, o-Aminobenzoylformic anhydride, Isatic acid lactam, Isatinic acid anhydride, 2,3-Indolinedione, Isatine, NSC 9262

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About This Item

Formula empirica (notazione di Hill):
C8H5NO2
Numero CAS:
91-56-5
Peso molecolare:
147.13
Beilstein:
383659
Numero CE:
202-077-8
Numero MDL:
MFCD00005718
Codice UNSPSC:
12352100
ID PubChem:
24847187
NACRES:
NA.22

Saggio

97%

Forma fisica

powder

Punto di fusione

193-195 °C (dec.) (lit.)

Solubilità

boiling water: soluble
diethyl ether: soluble
soluble

Stringa SMILE

O=C1Nc2ccccc2C1=O

InChI

1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
JXDYKVIHCLTXOP-UHFFFAOYSA-N

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Applicazioni

Isatin can be used as a reactant to prepare:
  • Phthalazinone derivatives.
  • Spirooxindole derivatives.
  • Agents against multidrug-resistant cells expressing P-glycoprotein.
  • Thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B.
  • Triazole-isatine compounds as potential antibacterial and antifungal agents.
  • Biologically relevant scaffolds such as spiro[indole-thiazolidinones].

It can be a reactant for:
  • Cascade reactions with heterocyclic ketene aminals.
  • Knoevenagel condensation reactions.

Isatin can also be used as a chromatographic spray reagent for amino acids, and also as a reference material in the preparation of indigo and Maya Blue. It is responsible for the yellow color exhibited by the "Maya Yellow" pigment.
Isatin undergoes Pd(II)-catalyzed C-H addition by direct sp2/sp3 C-H bond activation to form 3-substituted-3-hydroxy-2-oxindoles. Isatin derivatives (bis-Schiff base) are synthesized by the condensation of the natural or synthetic isatins with hydrazine.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

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Chengyuan Liang et al.
European journal of medicinal chemistry, 74, 742-750 (2013-11-02)
Eighteen symmetrical bis-Schiff base derivatives of isatin were synthesized by condensation of the natural or synthetic isatins with hydrazine and were evaluated for their in vitro and in vivo antitumor activities. More than half of the obtained compounds showed potent
Versatile three component procedure for combinatorial synthesis of biologically relevant scaffold spiro[indole-thiazolidinones] under aqueous conditions
Dandia, A.; et al.
Green Chemistry, 13, 1852-1852 (2011)
Demchuk, D. V.; et al.
Mendeleev Communications, 21, 224-224 (2011)
Gang-Wei Wang et al.
Organic letters, 15(20), 5270-5273 (2013-10-05)
The first Pd(II)-catalyzed C-H addition to isatins by direct sp(2)/sp(3) C-H bond activation for the construction of 3-substituted-3-hydroxy-2-oxindoles is reported. The bidentate nitrogen ligands were found to promote this reaction. Specifically, the preliminary bioassay indicated that 3-(5-chlorobenzoxazole)-3-hydroxy-N-benzyl-2-oxindole (2w) is a
From Maya Blue to "Maya Yellow": a connection between ancient nanostructured materials from the voltammetry of microparticles.
Antonio Doménech et al.
Angewandte Chemie (International ed. in English), 50(25), 5741-5744 (2011-05-11)
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