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N,N-Bis((S)-1-phenylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine

  • CAS No. 376355-58-7

  • Cat. No. CS-W011605
  • Purity≥98%
  • MDL No.MFCD08277033

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

N,N-Bis((S)-1-phenylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine|CS-W011605

Structure of 376355-58-7

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General Information

  • CAS No. 376355-58-7
  • Cat. No. CS-W011605
  • Purity ≥98%
  • MDL No. MFCD08277033
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₈H₂₆NO₂P
  • Molecular Weight 439.49
  • Synonym(s) N,N-Bis[(1S)-(-)-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine
  • SMILES C[C@@H](C1=CC=CC=C1)N([C@@H](C)C2=CC=CC=C2)P3OC4=C(C5=CC=CC=C5O3)C=CC=C4

Description

This chiral phosphine ligand features a rigid dibenzodioxaphosphepin scaffold with two (S)-1-phenylethyl groups, delivering enhanced steric bulk and electronic tuning. The amine-functionalized core enables robust coordination to transition metals, facilitating efficient catalysis in asymmetric synthesis under standard conditions.

Application

N,N-Bis((S)-1-phenylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine serves as a chiral, bench-stable phosphine ligand that enables stereoselective cross-coupling reactions. Its rigid dioxaphosphepin core provides strong electron-donating character and enhanced steric control, facilitating efficient palladium-catalyzed transformations. The (S)-1-phenylethyl groups confer high enantioselectivity in asymmetric synthesis, while the ligand exhibits excellent functional group tolerance and ease of purification—ideal for medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • 6-Chlorodibenzo[d,f][1,3,2]dioxaphosphepin|CS-0999885
      16611-68-0
    • rel-(R)-Bis((R)-1-phenylethyl)amine|CS-0095003
      21003-56-5
    • ~91%
    • In-stock
      N,N-Bis((S)-1-phenylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine|CS-W011605
      376355-58-7

    References

    • Smith, Craig R.; Rajanbabu Organic Letters, 2008 , vol. 10, # 8 p. 1657 - 1659
  • Route2
    • In-stock
      2,2'-Biphenol|CS-W016899
      1806-29-7
    • rel-(R)-Bis((R)-1-phenylethyl)amine|CS-0095003
      21003-56-5
    • ~%
    • In-stock
      N,N-Bis((S)-1-phenylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine|CS-W011605
      376355-58-7

    References

    • Alexakis; Rosset; Allamand; March; Guillen; Benhaim Synlett, 2001 , # 9 p. 1375 - 1378 Title/Abstract Full Text View citing articles Show Details D'Augustin, Magali; Palais, Laeticia; Alexakis, Alexandre Angewandte Chemie - International Edition, 2005 , vol. 44, # 9 p. 1376 - 1378
  • Route3
    • In-stock
      2,2'-Biphenol|CS-W016899
      1806-29-7
    • null|null
      777067-25-1
    • ~%
    • In-stock
      N,N-Bis((S)-1-phenylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine|CS-W011605
      376355-58-7

    References

    • Bournaud, Chloee; Falciola, Caroline; Thomas-Lecourt; Rosset, Stephane; Alexakis, Alexandre; Micouin, Laurent Organic Letters, 2006 , vol. 8, # 16 p. 3581 - 3584

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

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Computational Chemistry Data

  • TPSA   29.52
  • LogP   8.7504
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   5

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