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5-Chloro-1H-indazol-3-amine

  • CAS No. 5685-72-3

  • Cat. No. CS-0085350
  • Purity≥98%
  • MDL No.MFCD07385612

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

5-Chloro-1H-indazol-3-amine|CS-0085350

Structure of 5685-72-3

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General Information

  • CAS No. 5685-72-3
  • Cat. No. CS-0085350
  • Purity ≥98%
  • MDL No. MFCD07385612
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆ClN₃
  • Molecular Weight 167.60
  • Synonym(s) 3-Amino-5-chloro-1H-indazole
  • SMILES NC1=NNC2=C1C=C(Cl)C=C2

Description

5-Chloro-1H-indazol-3-amine is a bench-stable, electron-deficient heterocycle featuring a strategically positioned amine group. This compound integrates readily into medicinal chemistry scaffolds, offering a robust platform for coupling reactions and structural diversification in drug discovery programs.

Application

5-Chloro-1H-indazol-3-amine serves as a versatile building block in medicinal chemistry, enabling the construction of bioactive heterocycles through standard coupling reactions. Its chloro group facilitates palladium-catalyzed cross-coupling, while the primary amine supports derivatization via acylation, alkylation, or imine formation. The molecule exhibits bench stability and is compatible with common purification methods, making it ideal for iterative synthesis workflows targeting kinase inhibitors and other pharmaceutical scaffolds.

Synthesis

  • Route1

    References

    • Vasudevan, Anil; Souers, Andrew J.; Freeman, Jennifer C.; Verzal, Mary K.; Gao, Ju; Mulhern, Mathew M.; Wodka, Derek; Lynch, John K.; Engstrom, Kenneth M.; Wagaw, Seble H.; Brodjian, Sevan; Dayton, Brian; Falls, Doug H.; Bush, Eugene; Brune, Michael; Shapiro, Robin D.; Marsh, Kennan C.; Hernandez, Lisa E.; Collins, Christine A.; Kym, Philip R. Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 23 p. 5293 - 5297

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   54.7
  • LogP   1.7985
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   0

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