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CS-W001157 4
Total: USD 88.00

[2,2'-Bipyridine]-4,4'-dicarbonitrile

  • CAS No. 67491-43-4

  • Cat. No. CS-0091246
  • Purity≥95%
  • MDL No.MFCD06637688

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

[2,2'-Bipyridine]-4,4'-dicarbonitrile|CS-0091246

Structure of 67491-43-4

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General Information

  • CAS No. 67491-43-4
  • Cat. No. CS-0091246
  • Purity ≥95%
  • MDL No. MFCD06637688
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₆N₄
  • Molecular Weight 206.20
  • Synonym(s) 4,4'-Dicyano-2,2'-bipyridine
  • SMILES N#CC1=CC(C2=NC=CC(C#N)=C2)=NC=C1

Description

This bipyridine derivative features two nitrile groups at the 4 and 4′ positions, enhancing electron deficiency and enabling strong coordination with transition metals. The rigid planar structure supports efficient π-conjugation, making it ideal for constructing redox-active ligands in catalysis and molecular electronics.

Application

[2,2'-Bipyridine]-4,4'-dicarbonitrile serves as a versatile ligand in transition metal catalysis, enabling efficient coordination with late-stage metals such as palladium and ruthenium. Its dual nitrile groups enhance electronic modulation of the bipyridine core, improving catalyst stability and selectivity in cross-coupling and C–H functionalization reactions. The compound exhibits excellent bench stability and ease of purification, making it well-suited for reproducible, high-throughput synthetic workflows in medicinal chemistry and materials science.

Synthesis

  • Route1
    • [2,2'-Bipyridine]-4,4'-dicarboxamide|CS-0683331
      100137-02-8
    • ~90%
    • In-stock
      [2,2'-Bipyridine]-4,4'-dicarbonitrile|CS-0091246
      67491-43-4

    References

    • Baxter, Paul N.W.; Connor, Joseph A. Journal of Organometallic Chemistry, 1988 , vol. 355, p. 193 - 196
  • Route2
    • null|null
      773837-37-9
    • In-stock
      4,4'-Dibromo-2,2'-bipyridine|CS-W004595
      18511-71-2
    • ~63%
    • In-stock
      [2,2'-Bipyridine]-4,4'-dicarbonitrile|CS-0091246
      67491-43-4

    References

    • Duong, Adam; Maris, Thierry; Lebel, Olivier; Wuest, James D. Journal of Organic Chemistry, 2011 , vol. 76, # 5 p. 1333 - 1341
  • Route3

    References

    • Losse, Sebastian; Goerls, Helmar; Groarke, Robert; Vos, Johannes G.; Rau, Sven European Journal of Inorganic Chemistry, 2008 , # 28 p. 4448 - 4452

Safety Information

Download SDS
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

Quality Control

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Computational Chemistry Data

  • TPSA   73.36
  • LogP   1.88696
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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