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CS-W001157 4
Total: USD 88.00

3-Bromo-5-fluoropyridine

  • CAS No. 407-20-5

  • Cat. No. CS-W001250
  • Purity≥98%
  • MDL No.MFCD04112555

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

3-Bromo-5-fluoropyridine|CS-W001250

Structure of 407-20-5

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General Information

  • CAS No. 407-20-5
  • Cat. No. CS-W001250
  • Purity ≥98%
  • MDL No. MFCD04112555
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₃BrFN
  • Molecular Weight 175.99
  • Synonym(s) 5-Bromo-3-fluoropyridine; 3-Bromo-5-fluoropyridine
  • SMILES Fc1cncc(c1)Br

Description

3-Bromo-5-fluoropyridine is a halogenated pyridine derivative featuring complementary reactive sites for cross-coupling and functionalization. The bromo group enables palladium-catalyzed coupling, while the fluorine at the para position enhances electrophilicity and directs regioselective substitution. This dual functionality supports efficient synthesis of complex heterocycles in medicinal chemistry and materials science.

Application

3-Bromo-5-fluoropyridine serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal halogen reactivity. The bromine site undergoes efficient Suzuki, Stille, or Negishi coupling, while the fluorine substituent enhances metabolic stability and modulates electronic properties. Its bench-stable nature and compatibility with diverse reaction conditions make it a practical choice for constructing complex heterocyclic scaffolds and functionalized aryl derivatives in multi-step syntheses.

Synthesis

  • Route1

    References

    • Jaeschke, Georg; Kolczewski, Sabine; Porter, Richard Hugh Philip; Vieira, Eric Patent: US2006/199960 A1, 2006 ; Location in patent: Page/Page column 21 ; US 20060199960 A1
  • Route2

    References

    • Yamada, Shigeyuki; Knochel, Paul Synthesis, 2010 , # 14 art. no. T09010SS, p. 2490 - 2494
  • Route3

    References

    • Mallet, M.; Queguiner, G. Tetrahedron, 1986 , vol. 42, # 8 p. 2253 - 2262

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-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   12.89
  • LogP   1.9832
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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