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2-(5-Bromopyridin-3-yl)-1,3,4-oxadiazole

  • CAS No. 924869-13-6

  • Cat. No. CS-0199491
  • Molecule weight226.03
  • Purity≥98%
  • MDL No.None

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

2-(5-Bromopyridin-3-yl)-1,3,4-oxadiazole|CS-0199491

Structure of 924869-13-6

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General Information

  • CAS No. 924869-13-6
  • Cat. No. CS-0199491
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄BrN₃O
  • Molecular Weight 226.03
  • Synonym(s) 3-Bromo-5-(1,3,4-oxadiazol-2-yl)pyridine
  • SMILES C1=C(C=NC=C1Br)C2=NN=CO2

Description

This oxadiazole derivative features a brominated pyridine moiety enabling downstream functionalization via cross-coupling. The 1,3,4-oxadiazole ring imparts metabolic stability and enhances electron-withdrawing character, facilitating integration into bioactive scaffolds and materials with tailored electronic properties.

Application

2-(5-Bromopyridin-3-yl)-1,3,4-oxadiazole serves as a versatile heterocyclic building block for transition-metal-catalyzed cross-coupling reactions. The bromo group enables efficient Pd-catalyzed coupling with boronic acids, esters, and other nucleophiles, facilitating the construction of biaryl and extended π-conjugated systems. Its oxadiazole core provides excellent bench stability, mild functional group tolerance, and compatibility with standard purification methods, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • 5-Bromonicotinic acid Nicergoline Impurity|CS-0492508
      20826-04-4
    • null|null
      624-84-0
    • ~82%
    • In-stock
      2-(5-Bromopyridin-3-yl)-1,3,4-oxadiazole|CS-0199491
      924869-13-6

    References

    • Augustine, John Kallikat; Vairaperumal, Veeramani; Narasimhan, Sharmila; Alagarsamy, Padma; Radhakrishnan, Anbarasi Tetrahedron, 2009 , vol. 65, # 48 p. 9989 - 9996

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362

Quality Control

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Computational Chemistry Data

  • TPSA   51.81
  • LogP   1.8941
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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