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CS-W001157 4
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3-Iodo-1-methyl-1H-indazole

  • CAS No. 52088-10-5

  • Cat. No. CS-0051321
  • Purity≥96%
  • MDL No.MFCD09971239

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

3-Iodo-1-methyl-1H-indazole|CS-0051321

Structure of 52088-10-5

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General Information

  • CAS No. 52088-10-5
  • Cat. No. CS-0051321
  • Purity ≥96%
  • MDL No. MFCD09971239
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇IN₂
  • Molecular Weight 258.06
  • Synonym(s) None
  • SMILES CN1N=C(I)C2=C1C=CC=C2

Description

3-Iodo-1-methyl-1H-indazole is a heterocyclic iodide featuring a methylated indazole core with a reactive iodine at the 3-position. This substitution pattern enables facile cross-coupling reactions, making it a valuable scaffold for constructing complex pharmaceutical intermediates and bioactive molecules under standard conditions.

Application

3-Iodo-1-methyl-1H-indazole serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions for the construction of biologically relevant indazole scaffolds. The iodide group provides high reactivity in Suzuki, Stille, and Negishi couplings, while the methylated indazole core offers enhanced metabolic stability and favorable pharmacokinetic properties. Its bench-stable nature and ease of purification make it well-suited for iterative synthesis campaigns in API development.

Synthesis

  • Route1
    • In-stock
      3-Iodo-1H-indazole|CS-W003212
      66607-27-0
    • null|null
      74-88-4
    • ~87%
    • In-stock
      3-Iodo-1-methyl-1H-indazole|CS-0051321
      52088-10-5

    References

    • F. HOFFMANN-LA ROCHE AG; CHEN, Shaoqing; DE VICENTE FIDALGO, Javier; HAMILTON, Matthew Michael; HERMANN, Johannes Cornelius; KENNEDY-SMITH, Joshua; LI, Hongju; LOVEY, Allen John; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; LYNCH, Stephen M.; O'YANG, Counde; PADILLA, Fernando; SCHOENFELD, Ryan Craig; SIDDURI, Achyutharao; SOTH, Michael; WANG, Ce; WOVKULICH, Peter Michael; ZHANG, Xiaohu Patent: WO2013/30138 A1, 2013 ; Location in patent: Page/Page column 59; 60 ;
  • Route2

    References

    • F. HOFFMANN-LA ROCHE AG; CHEN, Shaoqing; DE VICENTE FIDALGO, Javier; HAMILTON, Matthew Michael; HERMANN, Johannes Cornelius; KENNEDY-SMITH, Joshua; LI, Hongju; LOVEY, Allen John; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; LYNCH, Stephen M.; O'YANG, Counde; PADILLA, Fernando; SCHOENFELD, Ryan Craig; SIDDURI, Achyutharao; SOTH, Michael; WANG, Ce; WOVKULICH, Peter Michael; ZHANG, Xiaohu Patent: WO2013/30138 A1, 2013 ;
  • Route3

    References

    • v. Auwers; Lohr Journal fuer Praktische Chemie (Leipzig), 1924 , vol. <2> 108, p. 314

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   17.82
  • LogP   2.1779
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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