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CS-W001157 4
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4-Chloroindolin-2-one

  • CAS No. 20870-77-3

  • Cat. No. CS-W022163
  • Purity≥97%
  • MDL No.MFCD03787567

*For research and further manufacturing use only, not for direct human use.

4-Chloroindolin-2-one|CS-W022163

Structure of 20870-77-3

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General Information

  • CAS No. 20870-77-3
  • Cat. No. CS-W022163
  • Purity ≥97%
  • MDL No. MFCD03787567
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆ClNO
  • Molecular Weight 167.59
  • Synonym(s) 4-Chlorooxindole
  • SMILES O=C1NC2=C(C(Cl)=CC=C2)C1

Description

4-Chloroindolin-2-one is a bench-stable heterocyclic scaffold featuring a chlorine substituent at the 4-position of the indolinone core. This electron-deficient moiety integrates readily into medicinal chemistry campaigns, serving as a key intermediate for kinase inhibitors and fluorescent probes due to its compatibility with diverse coupling reactions and structural rigidity.

Application

4-Chloroindolin-2-one serves as a versatile building block in medicinal chemistry, enabling efficient access to indole-based heterocycles. Its electron-deficient aromatic core facilitates electrophilic substitution and transition-metal-catalyzed coupling reactions. The carbonyl group supports nucleophilic addition and condensation processes, while the chlorine substituent provides a handle for further functionalization via cross-coupling or displacement reactions. Bench-stable and readily purified, it functions effectively in multi-step syntheses of bioactive molecules and API intermediates.

Synthesis

  • Route1

    References

    • Lin, Wei; Hu, Ming-Hua; Feng, Xian; Fu, Lei; Cao, Cheng-Pao; Huang, Zhi-Bin; Shi, Da-Qing Tetrahedron Letters, 2014 , vol. 55, # 14 p. 2238 - 2242
  • Route2
    • Methyl 2-(2-chloro-6-nitrophenyl)acetate|CS-1716992
      97522-09-3
    • ~82%
    • In-stock
      4-Chloroindolin-2-one|CS-W022163
      20870-77-3

    References

    • Quallich; Morrissey Synthesis, 1993 , # 1 p. 51 - 53
  • Route3
    • 2-(2-Amino-6-chlorophenyl)ethanol|CS-0206583
      100376-53-2
    • ~53%
    • In-stock
      4-Chloroindolin-2-one|CS-W022163
      20870-77-3

    References

    • Fujita, Ken-Ichi; Takahashi, Yoshinori; Owaki, Maki; Yamamoto, Kazunari; Yamaguchi, Ryohei Organic Letters, 2004 , vol. 6, # 16 p. 2785 - 2788

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   29.1
  • LogP   1.8346
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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