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7-Chloro-1H-indazole

  • CAS No. 37435-12-4

  • Cat. No. CS-0044712
  • Purity≥98%
  • MDL No.MFCD07368214

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

7-Chloro-1H-indazole|CS-0044712

Structure of 37435-12-4

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General Information

  • CAS No. 37435-12-4
  • Cat. No. CS-0044712
  • Purity ≥98%
  • MDL No. MFCD07368214
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅ClN₂
  • Molecular Weight 152.58
  • Synonym(s) 7-Chloroindazole
  • SMILES ClC1=CC=CC2=C1NN=C2

Description

7-Chloro-1H-indazole is a heterocyclic compound featuring a chlorine substituent at the 7-position of the indazole scaffold. This electron-deficient aromatic system enhances reactivity in cross-coupling processes and serves as a key pharmacophore in kinase inhibitor design. The molecule exhibits bench-stable handling characteristics and compatibility with standard synthetic protocols.

Application

7-Chloro-1H-indazole serves as a versatile heterocyclic building block in medicinal chemistry, enabling direct functionalization at the 3-position via palladium-catalyzed cross-coupling. Its electron-withdrawing chlorine substituent enhances metabolic stability and modulates basicity, while the indazole core provides favorable π-stacking interactions in target binding. Bench-stable and compatible with standard purification methods, it functions reliably in multistep synthesis of kinase inhibitors and CNS-active compounds.

Synthesis

  • Route1

    References

    • Lukin, Kirill; Hsu, Margaret C.; Fernando, Dilinie; Leanna, M. Robert Journal of Organic Chemistry, 2006 , vol. 71, # 21 p. 8166 - 8172
  • Route2

    References

    • Lokhande; Raheem, Abdul; Sabale; Chabukswar; Jagdale Tetrahedron Letters, 2007 , vol. 48, # 39 p. 6890 - 6892
  • Route3

    References

    • Ruechardt, Christoph; Hassmann, Volker Liebigs Annalen der Chemie, 1980 , # 6 p. 908 - 927

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   28.68
  • LogP   2.2163
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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