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CS-W001157 4
Total: USD 88.00

4-Hydroxy-2-(triphenylphosphonio)phenolate

  • CAS No. 5405-63-0

  • Cat. No. CS-0377926
  • Purity≥97%
  • MDL No.MFCD03938244

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

4-Hydroxy-2-(triphenylphosphonio)phenolate|CS-0377926

Structure of 5405-63-0

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General Information

  • CAS No. 5405-63-0
  • Cat. No. CS-0377926
  • Purity ≥97%
  • MDL No. MFCD03938244
  • Storage 4°C, stored under nitrogen, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₄H₁₉O₂P
  • Molecular Weight 370.38
  • Synonym(s) Triphenylphosphine-1,4-benzoquinone adduct (TPP-BQ)
  • SMILES [O-]C1=CC=C(C=C1[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)O

Description

This phosphonium phenolate features a hydroxyl group ortho to the phosphonium moiety, enabling facile deprotonation and enhanced nucleophilicity. The triphenylphosphine substituent imparts steric bulk and stabilizes the adjacent negative charge, facilitating use in polar solvents. Designed for synthetic applications requiring stable, reactive aryl anions under mild conditions.

Application

4-Hydroxy-2-(triphenylphosphonio)phenolate serves as a versatile synthon in transition-metal-catalyzed cross-coupling reactions, enabling efficient C–C bond formation at the ortho position of phenolic substrates. Its stable phosphonium functionality facilitates Stetter-type and Negishi-type couplings with high chemoselectivity, while the phenolate moiety provides enhanced solubility and compatibility with diverse reaction conditions. Ideal for bench-scale synthesis of functionalized biaryls and heterocyclic scaffolds, it offers predictable reactivity and straightforward purification.

Synthesis

  • Route1
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      603-35-0
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      106-51-4
    • ~92%
    • In-stock
      4-Hydroxy-2-(triphenylphosphonio)phenolate|CS-0377926
      5405-63-0

    References

    • Moiseev, Dmitry V.; Patrick, Brian O.; James, Brian R.; Hu, Thomas Q. Inorganica Chimica Acta, 2010 , vol. 363, # 13 p. 3569 - 3574
  • Route2
    • null|null
      603-35-0
    • null|null
      106-51-4
    • null|null
      71-43-2
    • ~%
    • In-stock
      4-Hydroxy-2-(triphenylphosphonio)phenolate|CS-0377926
      5405-63-0

    References

    • Schoenberg; Michaelis Chemische Berichte, 1936 , vol. 69, p. 1080

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS09
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H411
Precautionary Statements : P264-P270-P273-P301+P310-P330-P391-P501

Quality Control

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Computational Chemistry Data

  • TPSA   43.29
  • LogP   3.0852
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   4

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