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CS-W001157 4
Total: USD 88.00

4,4'-Dinitro-2,2'-bipyridine

  • CAS No. 18511-72-3

  • Cat. No. CS-W004581
  • Purity≥95%
  • MDL No.MFCD06657644

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

4,4'-Dinitro-2,2'-bipyridine|CS-W004581

Structure of 18511-72-3

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General Information

  • CAS No. 18511-72-3
  • Cat. No. CS-W004581
  • Purity ≥95%
  • MDL No. MFCD06657644
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₆N₄O₄
  • Molecular Weight 246.18
  • Synonym(s) 4,4'-Dinitro-2,2'-bipyridin
  • SMILES O=[N+]([O-])C1=CC(C2=NC=CC([N+]([O-])=O)=C2)=NC=C1

Application

4,4'-Dinitro-2,2'-bipyridine serves as a versatile ligand in transition metal catalysis, particularly in palladium- and copper-mediated cross-coupling reactions. Its electron-deficient bipyridine core enhances metal coordination strength and facilitates oxidative addition steps. The nitro groups provide synthetic handles for further functionalization via reduction or nucleophilic substitution, enabling access to diverse heterocyclic architectures. Bench-stable and readily purified by recrystallization, it functions effectively in both academic and industrial synthesis workflows.

Synthesis

  • Route1
    • null|null
      51595-55-2
    • ~59%
    • In-stock
      4,4'-Dinitro-2,2'-bipyridine|CS-W004581
      18511-72-3

    References

    • Ten Brink, Gerd-Jan; Arends, Isabel W. C. E.; Hoogenraad, Marcel; Verspui, Goeran; Sheldon, Roger A. Advanced Synthesis and Catalysis, 2003 , vol. 345, # 4 p. 497 - 505
  • Route2
    • null|null
      84175-12-2
    • ~92%
    • In-stock
      4,4'-Dinitro-2,2'-bipyridine|CS-W004581
      18511-72-3

    References

    • Wenkert, David; Woodward, R. B. Journal of Organic Chemistry, 1983 , vol. 48, # 3 p. 283 - 289
  • Route3

    References

    • Murase Nippon Kagaku Zasshi, 1956 , vol. 77, p. 682,685 Chem.Abstr., 1958 , p. 9100

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02,GHS06
Signal Word : Danger
UN#: 2926
Class : 4.1(6.1)
Packing Group : Ⅲ
Hazard Statements : H228-H301
Precautionary Statements : P210-P240-P241-P264-P270-P280-P330-P370+P378-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   112.06
  • LogP   1.96
  • H_Acceptors   6
  • H_Donors   0
  • Rotatable_Bonds   3

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