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CS-W001157 4
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6-Bromopyridin-3-ol

  • CAS No. 55717-45-8

  • Cat. No. CS-D0986
  • Purity≥98%
  • MDL No.MFCD04114184

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

6-Bromopyridin-3-ol|CS-D0986

Structure of 55717-45-8

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General Information

  • CAS No. 55717-45-8
  • Cat. No. CS-D0986
  • Purity ≥98%
  • MDL No. MFCD04114184
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄BrNO
  • Molecular Weight 174.00
  • Synonym(s) 6-Bromo-3-pyridinol
  • SMILES OC1=CC=C(Br)N=C1

Description

6-Bromopyridin-3-ol features a bromine substituent at the 6-position and a hydroxyl group at the 3-position on a pyridine core, delivering a uniquely reactive scaffold. This electron-deficient heterocycle integrates readily into cross-coupling reactions and serves as a key intermediate in medicinal chemistry.

Application

6-Bromopyridin-3-ol serves as a versatile building block in medicinal chemistry and catalytic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its well-established reactivity at the bromine site. The phenolic hydroxyl group provides orthogonal functionality for derivatization or protection, enhancing synthetic flexibility. Its bench-stable solid form facilitates handling and purification, making it suitable for scale-up applications in API development and heterocyclic library synthesis.

Synthesis

  • Route1

    References

    • Kumar, Sangit; Johansson, Henrik; Kanda, Takahiro; Engman, Lars; Mueller, Thomas; Bergenudd, Helena; Jonsson, Mats; Pedulli, Gian Franco; Amorati, Riccardo; Valgimigli, Luca Journal of Organic Chemistry, 2010 , vol. 75, # 3 p. 716 - 725
  • Route2

    References

    • KALYSPSYS, INC.; NOBLE, Stewart A.; OSHIRO, Guy; MALECHA, James W.; ZHAO, Cunxiang; ROBINSON, Carmen K. M.; DURON, Sergio G.; SERTIC, Michael; LINDSTROM, Andrew; SHIAU, Andrew; BAYNE, Christopher; KAHRAMAN, Mehmet; LOU, Boliang; GOVEK, Steven Patent: WO2006/55187 A1, 2006 ; Location in patent: Page/Page column 90 ; WO 2006/055187 A1
  • Route3

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 14, # 23 p. 5835 - 5839

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   33.12
  • LogP   1.5497
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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