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
• 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

Properties

• 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

Description

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.

Safety Information

• 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