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CS-W001157 4
Total: USD 88.00

Diphenyl(6-methyl-2-pyridyl)phosphine

  • CAS No. 132682-77-0

  • Cat. No. CS-0061378
  • Purity≥95%
  • MDL No.None

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

Diphenyl(6-methyl-2-pyridyl)phosphine|CS-0061378

Structure of 132682-77-0

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General Information

  • CAS No. 132682-77-0
  • Cat. No. CS-0061378
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₈H₁₆NP
  • Molecular Weight 277.30
  • Synonym(s) 2-Diphenylphosphino-6-methylpyridine
  • SMILES CC1=NC(=CC=C1)P(C2=CC=CC=C2)C3=CC=CC=C3

Description

Diphenyl(6-methyl-2-pyridyl)phosphine features a sterically hindered pyridyl group that enhances stability and modulates electronic properties. This bench-stable ligand integrates readily into palladium-catalyzed cross-coupling reactions, offering improved efficiency in challenging transformations.

Application

Diphenyl(6-methyl-2-pyridyl)phosphine serves as a robust, bench-stable ligand in palladium-catalyzed cross-coupling reactions. Its pyridyl moiety enhances electron density at phosphorus, improving catalyst activity and stability in Suzuki-Miyaura and Stille couplings. The 6-methyl substituent provides steric tuning and improves solubility, facilitating purification and scalability. This ligand is particularly effective in challenging coupling scenarios involving sterically hindered or electron-deficient substrates.

Synthesis

  • Route1
    • In-stock
      2-Chloro-6-methylpyridine|CS-W001993
      18368-63-3
    • null|null
      829-85-6
    • ~90%
    • In-stock
      Diphenyl(6-methyl-2-pyridyl)phosphine|CS-0061378
      132682-77-0

    References

    • Grotjahn, Douglas B.; Lev, Daniel A. Journal of the American Chemical Society, 2004 , vol. 126, # 39 p. 12232 - 12233
  • Route2
    • null|null
      1109288-90-5
    • ~87%
    • In-stock
      Diphenyl(6-methyl-2-pyridyl)phosphine|CS-0061378
      132682-77-0

    References

    • Li, Yuehui; Lu, Liang-Qiu; Das, Shoubhik; Pisiewicz, Sabine; Junge, Kathrin; Beller, Matthias Journal of the American Chemical Society, 2012 , vol. 134, # 44 p. 18325 - 18329
  • Route3
    • In-stock
      2-Bromo-6-methylpyridine|CS-W002190
      5315-25-3
    • null|null
      1079-66-9
    • ~77%
    • In-stock
      Diphenyl(6-methyl-2-pyridyl)phosphine|CS-0061378
      132682-77-0

    References

    • Shell Oil Company Patent: US5166411 A1, 1992 ;

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   12.89
  • LogP   3.14822
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   3

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