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CS-W001157 4
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(2'-Methyl-[1,1'-biphenyl]-2-yl)diphenylphosphine

  • CAS No. 402822-72-4

  • Cat. No. CS-W014486
  • Purity≥95%
  • MDL No.MFCD19441232

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

(2'-Methyl-[1,1'-biphenyl]-2-yl)diphenylphosphine|CS-W014486

Structure of 402822-72-4

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General Information

  • CAS No. 402822-72-4
  • Cat. No. CS-W014486
  • Purity ≥95%
  • MDL No. MFCD19441232
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₅H₂₁P
  • Molecular Weight 352.42
  • Synonym(s) Phosphine, (2'-methyl[1,1'-biphenyl]-2-yl)diphenyl-
  • SMILES CC1=CC=CC=C1C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4

Description

This diphenylphosphine derivative features a sterically hindered 2'-methyl-[1,1'-biphenyl] group that enhances its stability and electron-donating character. It serves as a robust ligand in palladium-catalyzed cross-coupling reactions, offering improved performance under standard conditions.

Application

(2'-Methyl-[1,1'-biphenyl]-2-yl)diphenylphosphine serves as a sterically hindered, electron-rich phosphine ligand that facilitates palladium-catalyzed cross-coupling reactions. Its modular biphenyl backbone provides enhanced stability and tunable steric bulk, enabling efficient coupling in Suzuki-Miyaura and Negishi transformations. The methyl substituent at the 2′-position improves oxidative stability and simplifies purification, making it well-suited for scalable synthesis and process chemistry applications.

Synthesis

  • Route1

    References

    • Joshaghani, Mohammad; Daryanavard, Marzieh; Rafiee, Ezzat; Nadri, Shirin Journal of Organometallic Chemistry, 2008 , vol. 693, # 19 p. 3135 - 3140
  • Route2
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      13175-77-4
    • ~71%
    • In-stock
      (2'-Methyl-[1,1'-biphenyl]-2-yl)diphenylphosphine|CS-W014486
      402822-72-4

    References

    • Baillie, Colin; Chen, Weiping; Xiao, Jianliang Tetrahedron Letters, 2001 , vol. 42, # 51 p. 9085 - 9088 Title/Abstract Full Text View citing articles Show Details Baillie, Colin; Xiao, Jianliang Tetrahedron, 2004 , vol. 60, # 19 p. 4159 - 4168
  • Route3

    References

    • Brauer, David J.; Hingst, Martin; Kottsieper, Konstantin W.; Liek, Christian; Nickel, Thomas; Tepper, Michael; Stelzer, Othmar; Sheldrick, William S. Journal of Organometalic Chemistry, 2002 , vol. 645, # 1-2 p. 14 - 26

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   0
  • LogP   5.42022
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   4

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