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CS-W001157 4
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5-Bromo-1H-indazol-3-ol

  • CAS No. 7364-27-4

  • Cat. No. CS-D0107
  • Molecule weight213.03
  • Purity≥97%
  • MDL No.MFCD10697926

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

5-Bromo-1H-indazol-3-ol|CS-D0107

Structure of 7364-27-4

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General Information

  • CAS No. 7364-27-4
  • Cat. No. CS-D0107
  • Purity ≥97%
  • MDL No. MFCD10697926
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BrN₂O
  • Molecular Weight 213.03
  • Synonym(s) 3H-Indazol-3-one, 5-bromo-1,2-dihydro-
  • SMILES O=C1NNC2=C1C=C(Br)C=C2

Description

5-Bromo-1H-indazol-3-ol features a brominated indazol-3-ol scaffold with enhanced electron density at the 3-position, enabling efficient coupling in cross-coupling reactions. The phenolic hydroxyl group supports direct derivatization and facilitates hydrogen bonding interactions in target binding. This bench-stable compound serves as a key intermediate for bioactive molecule synthesis.

Application

5-Bromo-1H-indazol-3-ol serves as a versatile building block for medicinal chemistry and materials science, enabling direct functionalization at the C3 position via palladium-catalyzed cross-coupling. The bromo group facilitates Suzuki, Stille, and Negishi reactions, while the phenolic OH supports derivatization and metal chelation. Its bench-stable crystalline form simplifies handling and purification in multi-step synthesis.

Synthesis

  • Route1

    References

    • SCHERING CORPORATION; KOZLOWSKI, Joseph, A.; YU, Wensheng; WONG, Michael, K.C.; KIM, Seong-Heon; TONG, Ling; LAVEY, Brian, J.; SHANKAR, Bandarpalle, B.; YANG, De-Yi; FELTZ, Robert; KOSINSKI, Aneta, Maria; ZHOU, Guowei; RIZVI, Razia, K.; DAI, Chaoyang; FIRE, Luke; GIRIJAVALLABHAN, Vinay, M.; LI, Dansu; POPOVICI-MULLER, Janeta; RICHARD, Judson, E.; ROSNER, Kristin, E.; SIDDIQUI, M., Arshad; YANG, Liping Patent: WO2010/54279 A1, 2010 ; Location in patent: Page/Page column 109-110 ; WO 2010/054279 A1
  • Route2
    • null|null
      141122-59-0
    • ~98%
    • In-stock
      5-Bromo-1H-indazol-3-ol|CS-D0107
      7364-27-4

    References

    • Dumitrascu, Florea; Plaveti, Marieta; Raileanu, Dan Revue Roumaine de Chimie, 1991 , vol. 36, # 8 p. 917 - 924
  • Route3
    • 5-Bromo-2-((carboxymethyl)amino)benzoic acid|CS-0367152
      32253-75-1
    • ~%
    • In-stock
      5-Bromo-1H-indazol-3-ol|CS-D0107
      7364-27-4

    References

    • Revue Roumaine de Chimie, , vol. 36, # 8 p. 917 - 924

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   48.65
  • LogP   1.6187
  • H_Acceptors   1
  • H_Donors   2
  • Rotatable_Bonds   0

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