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114618

Sigma-Aldrich

Isatin

97%

Sinônimo(s):

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

Fórmula empírica (Notação de Hill):
C8H5NO2
Número CAS:
91-56-5
Peso molecular:
147.13
Beilstein:
383659
Número CE:
202-077-8
Número MDL:
MFCD00005718
Código UNSPSC:
12352100
ID de substância PubChem:
24847187
NACRES:
NA.22

Ensaio

97%

Formulário

powder

pf

193-195 °C (dec.) (lit.)

solubilidade

boiling water: soluble
diethyl ether: soluble
soluble

grupo funcional

ketone

cadeia de caracteres SMILES

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)

chave InChI

JXDYKVIHCLTXOP-UHFFFAOYSA-N

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Aplicação

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
0000208075
BCCG8068
BCCG6072
0000121415
BCCF6671

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Sigma-Aldrich

679119

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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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