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5-Bromopyridin-2-ylboronic acid

  • CAS No. 652148-97-5

  • Cat. No. CS-0156779
  • Purity≥95%
  • MDL No.MFCD08705666

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

5-Bromopyridin-2-ylboronic acid|CS-0156779

Structure of 652148-97-5

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General Information

  • CAS No. 652148-97-5
  • Cat. No. CS-0156779
  • Purity ≥95%
  • MDL No. MFCD08705666
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅BBrNO₂
  • Molecular Weight 201.81
  • Synonym(s) 5-Bromopyridine-2-boronic acid
  • SMILES C1=CC(=NC=C1Br)B(O)O

Description

5-Bromopyridin-2-ylboronic acid features a pyridine ring bearing both bromo and boronic acid functionalities at adjacent positions. This dual-functionalized scaffold enables direct coupling in Suzuki-Miyaura reactions, delivering substituted pyridines with high efficiency. The boronic acid group exhibits excellent stability under standard conditions, while the bromo substituent serves as a complementary handle for cross-coupling or further functionalization.

Application

5-Bromopyridin-2-ylboronic acid serves as a versatile building block in palladium-catalyzed cross-coupling reactions, enabling efficient C–C bond formation with aryl and vinyl halides. Its bromine and boronic acid functionalities offer orthogonal reactivity for sequential transformations. The compound exhibits good bench stability, ease of handling, and compatibility with diverse reaction conditions, facilitating the construction of complex heterocyclic scaffolds common in medicinal chemistry and materials science.

Safety Information

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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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   53.35
  • LogP   -0.4761
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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