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Ethyl 3-iodo-1H-indazole-5-carboxylate

  • CAS No. 1279863-38-5

  • Cat. No. CS-0151727
  • Purity≥97%
  • MDL No.MFCD23704369

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

Ethyl 3-iodo-1H-indazole-5-carboxylate|CS-0151727

Structure of 1279863-38-5

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General Information

  • CAS No. 1279863-38-5
  • Cat. No. CS-0151727
  • Purity ≥97%
  • MDL No. MFCD23704369
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₉IN₂O₂
  • Molecular Weight 316.10
  • Synonym(s) 1H-Indazole-5-carboxylic acid, 3-iodo-, ethyl ester
  • SMILES CCOC(=O)C1=CC2=C(C=C1)NN=C2I

Description

Ethyl 3-iodo-1H-indazole-5-carboxylate features a strategically positioned iodine atom at the 3-position, enabling efficient late-stage functionalization via cross-coupling reactions. The indazole core provides robust heterocyclic stability, while the ester group offers synthetic versatility for further derivatization. This compound serves as a key intermediate in medicinal chemistry campaigns targeting kinase inhibitors and bioactive nitrogen heterocycles.

Application

Ethyl 3-iodo-1H-indazole-5-carboxylate serves as a versatile building block for constructing indazole-based scaffolds in medicinal chemistry. The iodine substituent enables palladium-catalyzed cross-coupling reactions, including Suzuki, Stille, and Negishi couplings, facilitating rapid diversification of the indazole core. The ester group provides a handle for selective derivatization, while the molecule exhibits good bench stability and ease of purification, making it well-suited for iterative synthesis campaigns and API precursor development.

Safety Information

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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   54.98
  • LogP   2.3442
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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