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CS-W001157 4
Total: USD 88.00

6-Bromo-1H-indazole

  • CAS No. 79762-54-2

  • Cat. No. CS-D0757
  • Purity≥98%
  • MDL No.MFCD03265457

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

6-Bromo-1H-indazole|CS-D0757

Structure of 79762-54-2

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General Information

  • CAS No. 79762-54-2
  • Cat. No. CS-D0757
  • Purity ≥98%
  • MDL No. MFCD03265457
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BrN₂
  • Molecular Weight 197.03
  • Synonym(s) None
  • SMILES BrC1=CC2=C(C=C1)C=NN2

Description

6-Bromo-1H-indazole is a bench-stable heterocyclic building block featuring a bromine substituent at the 6-position of the indazole core. This electron-deficient scaffold enables direct functionalization in cross-coupling reactions, facilitating rapid access to complex pharmaceutical intermediates and bioactive molecules under standard conditions.

Application

6-Bromo-1H-indazole serves as a versatile building block in medicinal chemistry, enabling direct functionalization via palladium-catalyzed cross-coupling reactions. Its bromine substituent facilitates Suzuki, Stille, and Negishi couplings, while the indazole core provides a bioisostere for purines and other heterocycles. The compound exhibits excellent bench stability and is compatible with a broad range of reaction conditions, making it ideal for constructing complex scaffolds in API development.

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

    • UNIVERSITY HEALTH NETWORK Patent: WO2009/79767 A1, 2009 ; Location in patent: Page/Page column 84 ; WO 2009/079767 A1
  • Route3

    References

    • Alcon, Inc. Patent: US2006/142307 A1, 2006 ; Location in patent: Page/Page column 8 ; US 20060142307 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H318
Precautionary Statements : P264-P270-P280-P301+P310-P305+P351+P338-P310-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   28.68
  • LogP   2.3254
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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