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CS-W001157 4
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1-Methyl-1H-indazole-3-carbaldehyde

  • CAS No. 4002-83-9

  • Cat. No. CS-W021348
  • Purity≥97%
  • MDL No.MFCD08060478

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

1-Methyl-1H-indazole-3-carbaldehyde|CS-W021348

Structure of 4002-83-9

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General Information

  • CAS No. 4002-83-9
  • Cat. No. CS-W021348
  • Purity ≥97%
  • MDL No. MFCD08060478
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈N₂O
  • Molecular Weight 160.17
  • Synonym(s) 3-Formyl-1-methyl-1H-indazole
  • SMILES O=CC1=NN(C)C2=C1C=CC=C2

Description

1-Methyl-1H-indazole-3-carbaldehyde features a conjugated aldehyde group fused to a nitrogen-rich heterocycle, enabling direct integration into Suzuki and Ugi-type coupling cascades. The methyl substituent enhances solubility and modulates electronic properties, while the indazole scaffold provides metabolic stability and favorable binding geometry in kinase-targeted drug discovery.

Application

1-Methyl-1H-indazole-3-carbaldehyde serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the aldehyde position for imine formation, reductive amination, or Grignard additions. Its indazole core provides metabolic stability and favorable π-stacking interactions, while the methyl group enhances solubility and reduces susceptibility to oxidation. The aldehyde functionality offers high reactivity in standard coupling protocols, facilitating rapid access to diverse heterocyclic scaffolds and drug-like molecules.

Synthesis

  • Route1

    References

    • ASTRAZENECA AB Patent: WO2005/66132 A1, 2005 ; Location in patent: Page/Page column 45-46 ; WO 2005/066132 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 : 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   34.89
  • LogP   1.3858
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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