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CS-W001157 4
Total: USD 88.00

(5-Bromo-2-fluoropyridin-3-yl)boronic acid

  • CAS No. 501435-91-2

  • Cat. No. CS-W009509
  • Purity≥96%
  • MDL No.MFCD04039317

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

(5-Bromo-2-fluoropyridin-3-yl)boronic acid|CS-W009509

Structure of 501435-91-2

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General Information

  • CAS No. 501435-91-2
  • Cat. No. CS-W009509
  • Purity ≥96%
  • MDL No. MFCD04039317
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄BBrFNO₂
  • Molecular Weight 219.80
  • Synonym(s) 5-Bromo-2-fluoropyridine-3-boronic acid
  • SMILES OB(C1=CC(Br)=CN=C1F)O

Description

This boronate moiety integrates seamlessly into Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation under standard conditions. The electron-deficient pyridine ring enhances reactivity, while the ortho-halogen substitution pattern supports selective functionalization. Bench-stable and moisture-tolerant, it streamlines synthesis in medicinal chemistry and materials science applications.

Application

(5-Bromo-2-fluoropyridin-3-yl)boronic acid serves as a versatile building block in palladium-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl architectures. The ortho-fluoro and bromo substituents provide complementary reactivity for sequential functionalization, while the boronic acid group offers excellent bench stability and compatibility with standard Suzuki-Miyaura coupling conditions. Its defined regiochemistry and predictable transformation profile make it ideal for targeted synthesis of pharmaceutical intermediates and agrochemical scaffolds.

Synthesis

  • Route1

    References

    • Sutherland, Andrew; Gallagher, Timothy Journal of Organic Chemistry, 2003 , vol. 68, # 8 p. 3352 - 3355

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   53.35
  • LogP   -0.337
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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