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CS-W001157 4
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6-Nitroindolin-2-one

  • CAS No. 474799-41-2

  • Cat. No. CS-0037174
  • Purity≥95%
  • MDL No.MFCD09835636

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

6-Nitroindolin-2-one|CS-0037174

Structure of 474799-41-2

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General Information

  • CAS No. 474799-41-2
  • Cat. No. CS-0037174
  • Purity ≥95%
  • MDL No. MFCD09835636
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆N₂O₃
  • Molecular Weight None
  • Synonym(s) 6-Nitrooxindole
  • SMILES O=C1CC2=CC=C([N+]([O-])=O)C=C2N1

Description

6-Nitroindolin-2-one features a fused indolinone core bearing a nitro group at the 6-position, conferring enhanced electron deficiency and reactivity. This structural motif enables efficient incorporation into photolabile systems, where the nitro group facilitates rapid cleavage upon UV irradiation. The compound exhibits bench-stable handling characteristics and integrates readily into peptide and small-molecule scaffolds requiring controlled release functionality.

Application

6-Nitroindolin-2-one serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted indole scaffolds through reductive transformations and nucleophilic additions. Its electron-deficient nature enhances reactivity in transition-metal-catalyzed couplings, while the nitro group facilitates selective functionalization. The compound exhibits good bench stability and is compatible with common protecting group strategies, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • null|null
      185433-47-0
    • ~70%
    • In-stock
      6-Nitroindolin-2-one|CS-0037174
      474799-41-2

    References

    • Roth, Gerald J.; Heckel, Armin; Colbatzky, Florian; Handschuh, Sandra; Kley, Joerg; Lehmann-Lintz, Thorsten; Lotz, Ralf; Tontsch-Grunt, Ulrike; Walter, Rainer; Hilberg, Frank Journal of Medicinal Chemistry, 2009 , vol. 52, # 14 p. 4466 - 4480
  • Route2
    • Methyl 2-(2,4-dinitrophenyl)acetate|CS-0130247
      58605-12-2
    • ~%
    • In-stock
      6-Nitroindolin-2-one|CS-0037174
      474799-41-2

    References

    • Carruthers, Nicholas I.; Chai, Wenying; Dax, Scott L.; Jablonowski, Jill A.; Li, Xiaobing; Lovenberg, Timothy W.; Murray, William V.; Rudolph, Dale A.; Seierstad, Mark; Youngman, Mark A. Patent: US2005/70534 A1, 2005 ; Location in patent: Page/Page column 13 ; US 20050070534 A1
  • Route3

    References

    • Cao, Jingrong; Gao, Huai; Bemis, Guy; Salituro, Francesco; Ledeboer, Mark; Harrington, Edmund; Wilke, Susanne; Taslimi, Paul; Pazhanisamy; Xie, Xiaoling; Jacobs, Marc; Green, Jeremy Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 10 p. 2891 - 2895

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   72.24
  • LogP   1.0894
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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