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CS-W001157 4
Total: USD 88.00

5-Methyl-2,2'-bipyridine

  • CAS No. 56100-20-0

  • Cat. No. CS-0036667
  • Purity≥96%
  • MDL No.MFCD08062569

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

5-Methyl-2,2'-bipyridine|CS-0036667

Structure of 56100-20-0

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General Information

  • CAS No. 56100-20-0
  • Cat. No. CS-0036667
  • Purity ≥96%
  • MDL No. MFCD08062569
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₀N₂
  • Molecular Weight None
  • Synonym(s) Carbamicacid,[(1S,3R)-3-(aminomethyl)cyclop entyl]-,1,1-dimethylethylester(14CI)
  • SMILES CC(C=C1)=CN=C1C2=NC=CC=C2

Description

5-Methyl-2,2'-bipyridine is a bench-stable, electron-rich ligand featuring a methyl group at the 5-position of one pyridine ring. This substitution enhances π-donation and stabilizes metal complexes in coordination chemistry. The molecule integrates readily into catalytic systems, particularly in transition-metal-mediated cross-coupling and photoredox processes. Its steric profile supports selective complexation without compromising solubility in common organic solvents.

Application

5-Methyl-2,2'-bipyridine serves as a robust chelating ligand in transition metal catalysis, particularly in palladium- and copper-mediated cross-coupling reactions. Its methyl substitution enhances solubility and electronic tuning while maintaining excellent bench stability and ease of purification. Functions effectively in complex reaction environments due to high coordination strength and compatibility with diverse functional groups.

Synthesis

  • Route1
    • null|null
      78-85-3
    • In-stock
      1-(2-Oxo-2-(pyridin-2-yl)ethyl)pyridin-1-ium iodide|CS-0450337
      26482-00-8
    • ~94%
    • In-stock
      5-Methyl-2,2'-bipyridine|CS-0036667
      56100-20-0

    References

    • Esch, J. H. van; Hoffmann, M. A. M.; Nolte, R. J. M. Journal of Organic Chemistry, 1995 , vol. 60, # 6 p. 1599 - 1610
  • Route2
    • In-stock
      2-Bromo-5-methylpyridine|CS-W007353
      3510-66-5
    • null|null
      17997-47-6
    • ~75%
    • In-stock
      5-Methyl-2,2'-bipyridine|CS-0036667
      56100-20-0

    References

    • Hyun, Soo Lee; Schultz, Peter G. Journal of the American Chemical Society, 2008 , vol. 130, # 40 p. 13194 - 13195
  • Route3

    References

    • Blakemore, David C.; Marples, Louise A. Tetrahedron Letters, 2011 , vol. 52, # 32 p. 4192 - 4195

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-P305+P351+P338-P332+P313-P337+P313-P362+P364

Quality Control

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Computational Chemistry Data

  • TPSA   25.78
  • LogP   2.45202
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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