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114618

Sigma-Aldrich

Isatin

97%

Synonym(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

Empirical Formula (Hill Notation):
C8H5NO2
CAS Number:
91-56-5
Molecular Weight:
147.13
Beilstein/REAXYS Number:
383659
EC Number:
202-077-8
MDL number:
MFCD00005718
UNSPSC Code:
12352100
PubChem Substance ID:
24847187
NACRES:
NA.22

Quality Level

100

assay

97%

form

powder

mp

193-195 °C (dec.) (lit.)

solubility

boiling water: soluble
diethyl ether: soluble
soluble

SMILES string

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)

InChI key

JXDYKVIHCLTXOP-UHFFFAOYSA-N

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Application

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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