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5-Chloro-1H-indazole-3-carbaldehyde

  • CAS No. 102735-84-2

  • Cat. No. CS-0042987
  • Purity≥97%
  • MDL No.MFCD07781535

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

5-Chloro-1H-indazole-3-carbaldehyde|CS-0042987

Structure of 102735-84-2

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General Information

  • CAS No. 102735-84-2
  • Cat. No. CS-0042987
  • Purity ≥97%
  • MDL No. MFCD07781535
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅ClN₂O
  • Molecular Weight 180.59
  • Synonym(s) 5-CHLORO-3-(1H)INDAZOLE CARBOXALDEHYDE
  • SMILES ClC1=CC=C2NN=C(C=O)C2=C1

Description

5-Chloro-1H-indazole-3-carbaldehyde delivers a potent electron-deficient heterocyclic scaffold featuring a reactive aldehyde group at the 3-position. This configuration enables direct coupling in amide bond formation and facilitates integration into bioactive molecules. The chloro substituent enhances metabolic stability and modulates electronic properties, making it valuable for medicinal chemistry and targeted synthesis.

Application

5-Chloro-1H-indazole-3-carbaldehyde serves as a versatile building block for heterocyclic synthesis, enabling efficient access to indazole-based scaffolds in medicinal chemistry. The aldehyde functionality facilitates reductive amination, Wittig reactions, and coupling with nucleophiles, while the chloro substituent supports further functionalization via palladium-catalyzed cross-coupling. Bench-stable and readily purified by recrystallization, it functions effectively in standard synthetic workflows requiring orthogonality and predictable reactivity.

Synthesis

  • Route1
    • (5-Chloro-2h-indazol-3-yl)methanol|CS-0684432
      102735-90-0
    • ~64%
    • In-stock
      5-Chloro-1H-indazole-3-carbaldehyde|CS-0042987
      102735-84-2

    References

    • Buechi, George; Lee, Gary C. M.; Yang, David; Tannenbaum, Steven R. Journal of the American Chemical Society, 1986 , vol. 108, # 14 p. 4115 - 4119
  • Route2

    References

    • US2003/207883 A1, ; Page/Page column 85 ;
  • Route3

    References

    • Journal of the American Chemical Society, , vol. 108, # 14 p. 4115 - 4119

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

Quality Control

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Computational Chemistry Data

  • TPSA   45.75
  • LogP   2.0288
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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