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Merck

114618

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24847187
EC Number:
202-077-8
Beilstein/REAXYS Number:
383659
MDL number:
MFCD00005718
Assay:
97%
Form:
powder

Key Documents

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InChI key

JXDYKVIHCLTXOP-UHFFFAOYSA-N

InChI

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

SMILES string

O=C1Nc2ccccc2C1=O

assay

97%

form

powder

mp

193-195 °C (dec.) (lit.)

solubility

boiling water: soluble, diethyl ether: soluble, soluble

functional group

ketone

Quality Level

100

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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

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000505987
0000505987
BCCN6252
0000469797
0000469797

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Novel Synthesis of Some Phthalazinone Derivatives
Mahmoud, M. R.; et al.
Chin. J. Chem., 29, 1446-1450 (2011)
Fuchao Yu et al.
Organic letters, 13(18), 4782-4785 (2011-08-19)
A concise and efficient route for the synthesis of highly substituted imidazopyrroloquinoline derivatives by simply refluxing a reaction mixture of different types of isatins and heterocyclic ketene aminals (HKAs) by acetic acid was developed. This method is suitable for combinatorial
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
Ozil, M.; et al.
J. Chem. Res. (M), 35, 268-268 (2011)
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)
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