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CS-W001157 4
Total: USD 88.00

Bis(2-naphthyl)phosphine oxide

  • CAS No. 78871-05-3

  • Cat. No. CS-0098782
  • Purity≥97%
  • MDL No.None

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

Bis(2-naphthyl)phosphine oxide|CS-0098782

Structure of 78871-05-3

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General Information

  • CAS No. 78871-05-3
  • Cat. No. CS-0098782
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₀H₁₅OP
  • Molecular Weight 302.31
  • Synonym(s) Phosphine oxide, di-2-naphthalenyl-
  • SMILES O=P(C1=CC=C2C=CC=CC2=C1)C3=CC=C4C=CC=CC4=C3

Description

Bis(2-naphthyl)phosphine oxide features a rigid, electron-rich phosphine oxide core that enhances ligand stability and coordination versatility. This sterically encumbered structure promotes selective metal binding in catalytic systems, particularly in palladium-catalyzed cross-coupling reactions. The molecule exhibits robust bench stability and tolerates air and moisture during handling.

Application

Bis(2-naphthyl)phosphine oxide serves as a stable, bench-friendly ligand in transition metal catalysis, particularly in palladium- and nickel-catalyzed cross-coupling reactions. Its electron-donating character and steric profile enhance catalyst activity and selectivity in C–C and C–heteroatom bond formations. The molecule exhibits excellent functional group tolerance and facilitates efficient purification due to its low volatility and thermal stability.

Synthesis

  • Route1
    • null|null
      762-04-9
    • ~54%
    • In-stock
      Bis(2-naphthyl)phosphine oxide|CS-0098782
      78871-05-3

    References

    • Takeda Chemical Industries, Ltd. Patent: EP1452537 A1, 2004 ; Location in patent: Page 30 ;
  • Route2
    • In-stock
      2-Bromonaphthalene|CS-W007537
      580-13-2
    • null|null
      762-04-9
    • ~%
    • In-stock
      Bis(2-naphthyl)phosphine oxide|CS-0098782
      78871-05-3

    References

    • Hatano, Manabu; Horibe, Takahiro; Ishihara, Kazuaki Angewandte Chemie - International Edition, 2013 , vol. 52, # 17 p. 4549 - 4553 Angew. Chem., 2013 , vol. 125, # 17 p. 4647 - 4651,5
  • Route3
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      21473-01-8
    • null|null
      2303-76-6
    • ~%
    • In-stock
      Bis(2-naphthyl)phosphine oxide|CS-0098782
      78871-05-3

    References

    • Hobbs, Charles F.; Knowles, W. S. Journal of Organic Chemistry, 1981 , vol. 46, p. 4422 - 4427

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   17.07
  • LogP   4.5035
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   2

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