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

  • CAS No. 885271-25-0

  • Cat. No. CS-0041089
  • Purity≥98%
  • MDL No.MFCD06739144

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

Methyl 3-iodo-1H-indazole-5-carboxylate|CS-0041089

Structure of 885271-25-0

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General Information

  • CAS No. 885271-25-0
  • Cat. No. CS-0041089
  • Purity ≥98%
  • MDL No. MFCD06739144
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇IN₂O₂
  • Molecular Weight 302.07
  • Synonym(s) 3-IODO-1H-INDAZOLE-5-CARBOXYLIC ACID METHYL ESTER
  • SMILES O=C(C1=CC2=C(NN=C2I)C=C1)OC

Description

Methyl 3-iodo-1H-indazole-5-carboxylate is a bench-stable, moisture-tolerant building block featuring a strategically positioned iodine atom at the 3-position and a carboxylate ester at the 5-position. This combination enables efficient late-stage diversification via cross-coupling reactions, particularly in palladium-catalyzed transformations. The electron-deficient indazole core enhances reactivity in Suzuki-Miyaura and Negishi protocols, while the methyl ester group provides synthetic handle flexibility for downstream derivatization.

Application

Methyl 3-iodo-1H-indazole-5-carboxylate serves as a versatile building block for transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl scaffolds. The iodide functionality exhibits high reactivity in palladium-catalyzed coupling processes, while the methyl ester group provides compatibility with standard functional group manipulations. Its bench-stable nature and orthogonal reactivity profile facilitate integration into multi-step synthetic sequences for medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • WO2006/86255 A2, ; Page/Page column 85; 86 ; WO 2006/086255 A2

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   54.98
  • LogP   1.9541
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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