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CS-W001157 4
Total: USD 88.00

[2,2'-Bipyridine]-4,4'-diyldiboronic acid

  • CAS No. 159614-36-5

  • Cat. No. CS-0110282
  • Purity≥95%
  • MDL No.MFCD18261481

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

[2,2'-Bipyridine]-4,4'-diyldiboronic acid|CS-0110282

Structure of 159614-36-5

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General Information

  • CAS No. 159614-36-5
  • Cat. No. CS-0110282
  • Purity ≥95%
  • MDL No. MFCD18261481
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₀B₂N₂O₄
  • Molecular Weight 243.82
  • Synonym(s) 2,2'-Bipyridine-4,4'-diboronic acid
  • SMILES OB(O)C1=CC(C2=NC=CC(B(O)O)=C2)=NC=C1

Description

This boronate moiety features two bipyridine-directed coordination sites, enabling robust chelation in transition metal complexes. The diol-functionalized boronic acid handles integrate readily into Suzuki-Miyaura coupling protocols under standard conditions, delivering stable heteroaryl linkages with high fidelity and minimal side-product formation.

Application

[2,2'-Bipyridine]-4,4'-diyldiboronic acid serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling the construction of biaryl and polycyclic heteroaromatic scaffolds. Its dual boronic acid functionality offers high reactivity in Suzuki-Miyaura coupling protocols, with excellent stability under ambient conditions and compatibility with diverse functional groups. The molecule functions effectively as a ligand precursor and is well-suited for applications in materials science and medicinal chemistry synthesis.

Synthesis

  • Route1
    • In-stock
      4,4'-Dibromo-2,2'-bipyridine|CS-W004595
      18511-71-2
    • null|null
      5419-55-6
    • ~%
    • In-stock
      [2,2'-Bipyridine]-4,4'-diyldiboronic acid|CS-0110282
      159614-36-5

    References

    • Nakashima, Kazuaki; Shinkai, Seiji Chemistry Letters, 1994 , # 7 p. 1267 - 1270

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-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   106.7
  • LogP   -2.4968
  • H_Acceptors   6
  • H_Donors   4
  • Rotatable_Bonds   3

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