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Merck
CN

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
Beilstein:
383659
EC Number:
202-077-8
MDL number:
MFCD00005718
UNSPSC Code:
12352100
PubChem Substance ID:
24847187
NACRES:
NA.22

Key Documents

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Quality Level

100

Assay

97%

form

powder

mp

193-195 °C (dec.) (lit.)

solubility

boiling water: soluble
diethyl ether: soluble
soluble

functional group

ketone

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 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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Certificates of Analysis (COA)

Lot/Batch Number
0000505987
0000505987
BCCN6252
0000469797
0000469797

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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
Novel Synthesis of Some Phthalazinone Derivatives
Mahmoud, M. R.; et al.
Chin. J. Chem., 29, 1446-1450 (2011)
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)
Demchuk, D. V.; et al.
Mendeleev Communications, 21, 224-224 (2011)
Ozil, M.; et al.
J. Chem. Res. (M), 35, 268-268 (2011)
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