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CS-W001157 4
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1H-indazole-5-carbaldehyde

  • CAS No. 253801-04-6

  • Cat. No. CS-W019749
  • Purity≥97%
  • MDL No.MFCD06738280

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

1H-indazole-5-carbaldehyde|CS-W019749

Structure of 253801-04-6

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General Information

  • CAS No. 253801-04-6
  • Cat. No. CS-W019749
  • Purity ≥97%
  • MDL No. MFCD06738280
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆N₂O
  • Molecular Weight 146.15
  • Synonym(s) 1H-Indazole-5-carboxaldehyde
  • SMILES O=CC1=CC2=C(NN=C2)C=C1

Description

1H-indazole-5-carbaldehyde features a reactive aldehyde group positioned at the 5-position of the indazole core, enabling direct functionalization in C–H activation and transition-metal-catalyzed coupling reactions. This electron-deficient heterocycle integrates readily into bioactive scaffolds and conjugated systems, offering high stability under standard conditions and compatibility with diverse synthetic transformations.

Application

1H-indazole-5-carbaldehyde serves as a versatile building block in medicinal chemistry, enabling efficient access to biologically active heterocycles through standard aldehyde transformations. Its well-defined reactivity facilitates nucleophilic additions, condensations, and coupling reactions with high functional group tolerance. The molecule exhibits bench stability and clean purification profiles, making it suitable for scalable synthesis and fragment-based drug discovery applications.

Synthesis

  • Route1
    • In-stock
      5-Bromo-1H-indazole|CS-B0441
      53857-57-1
    • null|null
      68-12-2
    • ~50%
    • In-stock
      1H-indazole-5-carbaldehyde|CS-W019749
      253801-04-6

    References

    • Shafer, Cynthia M.; Lindvall, Mika; Bellamacina, Cornelia; Gesner, Thomas G.; Yabannavar, Asha; Jia, Weiping; Lin, Song; Walter, Annette Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 16 p. 4482 - 4485
  • Route2

    References

    • IMCLONE SYSTEMS INCORPORATED Patent: WO2005/813 A1, 2005 ; Location in patent: Page 36 ; WO 2005/000813 A1
  • Route3
    • null|null
      68-12-2
    • ~50%
    • In-stock
      1H-indazole-5-carbaldehyde|CS-W019749
      253801-04-6

    References

    • NOVARTIS VACCINES AND DIAGNOSTICS, INC. Patent: WO2007/124288 A1, 2007 ; Location in patent: Page/Page column 50 ; WO 2007/124288 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H319
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   45.75
  • LogP   1.3754
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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