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CS-W001157 4
Total: USD 88.00

4'-Methyl-[2,2'-bipyridine]-4-carboxylic acid

  • CAS No. 103946-54-9

  • Cat. No. CS-0085074
  • Purity≥98%
  • MDL No.MFCD11112059

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

4'-Methyl-[2,2'-bipyridine]-4-carboxylic acid|CS-0085074

Structure of 103946-54-9

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General Information

  • CAS No. 103946-54-9
  • Cat. No. CS-0085074
  • Purity ≥98%
  • MDL No. MFCD11112059
  • Storage RT, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₀N₂O₂
  • Molecular Weight 214.22
  • Synonym(s) 4'-Methyl-2,2'-bipyridine-4-carboxylic acid
  • SMILES O=C(O)C=1C=CN=C(C1)C=2N=CC=C(C2)C

Description

4'-Methyl-[2,2'-bipyridine]-4-carboxylic acid features a methyl-substituted bipyridine core paired with a carboxylic acid at the 4-position, enabling robust metal coordination and enhanced solubility in polar solvents. This structure facilitates integration into chelating ligands for transition metal complexes and functionalized materials.

Application

4'-Methyl-[2,2'-bipyridine]-4-carboxylic acid serves as a versatile ligand scaffold in transition metal catalysis, offering enhanced solubility and steric modulation compared to unsubstituted bipyridines. The carboxylic acid group enables direct conjugation or derivatization for coordination to metals, while the methyl substituent improves electronic tuning and bench stability. It functions effectively in palladium-catalyzed cross-coupling and copper-mediated cyclizations, facilitating efficient access to functionalized heterocyclic architectures common in pharmaceutical and materials chemistry.

Synthesis

  • Route1

    References

    • Aldridge III, W. Steven; Hornstein, Brooks J.; Serron, Scafford; Dattelbaum, Dana M.; Schoonover, Jon R.; Meyer, Thomas J. Journal of Organic Chemistry, 2006 , vol. 71, # 14 p. 5186 - 5190
  • Route2

    References

    • Kikkeri, Raghavendra; Liu, Xinyu; Adibekian, Alexander; Tsai, Yu-Hsuan; Seeberger, Peter H. Chemical Communications, 2010 , vol. 46, # 13 p. 2197 - 2199
  • Route3

    References

    • Australian Journal of Chemistry, , vol. 39, # 7 p. 1053 - 1062

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   63.08
  • LogP   2.15022
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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