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114618

Sigma-Aldrich

Isatin

97%

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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
Empirical Formula (Hill Notation):
C8H5NO2
CAS Number:
Molecular Weight:
147.13
Beilstein:
383659
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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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This Item
1435391271959539
Isatin 97%

Sigma-Aldrich

114618

Isatin

(S)-BIDIME ≥97%

Sigma-Aldrich

912719

(S)-BIDIME

form

powder

form

-

form

powder

form

solid

mp

193-195 °C (dec.) (lit.)

mp

-

mp

-

mp

46-50 °C

solubility

boiling water: soluble, diethyl ether: soluble

solubility

diethyl ether: 0.1 g/10 mL, clear, colorless

solubility

-

solubility

-

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

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 Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
Step-economic, efficient, ZnS nanoparticle-catalyzed synthesis of spirooxindole derivatives in aqueous medium viaKnoevenagel condensation followed by Michael addition
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Green Chemistry, 13, 2135-2145 (2011)
Novel Synthesis of Some Phthalazinone Derivatives
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Chin. J. Chem., 29, 1446-1450 (2011)
Versatile three component procedure for combinatorial synthesis of biologically relevant scaffold spiro[indole-thiazolidinones] under aqueous conditions
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Ozil, M.; et al.
J. Chem. Res. (M), 35, 268-268 (2011)

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