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114618 Aldrich

Isatin

Synonym: 2,3-Dioxo-2,3-dihydroindole, 2,3-Diketoindoline, 2,3-Dioxoindoline, 2,3-Indolinedione, o-Aminobenzoylformic anhydride, Isatic acid lactam, Isatine, Isatinic acid anhydride, NSC 9262

  • CAS Number 91-56-5

  • Empirical Formula (Hill Notation) C8H5NO2

  • Molecular Weight 147.13

  •  Beilstein Registry Number 383659

  •  EC Number 202-077-8

  •  MDL number MFCD00005718

  •  PubChem Substance ID 24847187

  • Popular Documents:  FTNMR (PDF)  

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Properties

Related Categories Building Blocks, C7 to C9, Chemical Synthesis, Heterocyclic Building Blocks, Indoles More...
InChI Key   JXDYKVIHCLTXOP-UHFFFAOYSA-N
mp   193-195 °C (dec.)(lit.)
solubility   : soluble
  boiling water: soluble
  diethyl ether: soluble

Description

Packaging

5, 100, 500 g in poly bottle

Application

Isatin is used as a reference material in the preparation of indigo and Maya Blue. It is also responsible for the yellow color exhibited by the “Maya Yellow” pigment.

Reactant for preparation of:
• 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]

Reactant for:
• Cascade reactions with heterocyclic ketene aminals
• Knoevenagel condensation reactions

General description

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.

Price and Availability

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
1
RTECS 
NL7873000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles
Peer-Reviewed Papers
15

References

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