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Methyl 2-(triphenylphosphoranylidene)propanoate

  • CAS No. 2605-68-7

  • Cat. No. CS-0030442
  • Purity≥97%
  • MDL No.MFCD08062441

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

Methyl 2-(triphenylphosphoranylidene)propanoate|CS-0030442

Structure of 2605-68-7

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General Information

  • CAS No. 2605-68-7
  • Cat. No. CS-0030442
  • Purity ≥97%
  • MDL No. MFCD08062441
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₂H₂₁O₂P
  • Molecular Weight 348.37
  • Synonym(s) Propionicacid, 2-(triphenylphosphoranylidene)-, methyl ester
  • SMILES CC(C(OC)=O)=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3

Description

Methyl 2-(triphenylphosphoranylidene)propanoate is a stable, bench-ready phosphonate ylide that enables efficient Wittig-type olefination. Featuring a sterically shielded phosphorus center and a reactive α,β-unsaturated ester moiety, it facilitates high-yield synthesis of terminal alkenes under mild conditions. This reagent delivers predictable stereochemistry and integrates seamlessly into synthetic workflows requiring controlled C=C bond formation.

Application

Methyl 2-(triphenylphosphoranylidene)propanoate serves as a stable, bench-ready phosphorus ylide reagent for the synthesis of α,β-unsaturated carbonyl compounds via Wittig reactions. It enables efficient conversion of aldehydes to (E)-alkenes with high stereoselectivity and facilitates the construction of conjugated systems in natural product and pharmaceutical intermediate synthesis. The triphenylphosphine oxide byproduct is readily removed during purification.

Synthesis

  • Route1
    • Methyl 2-(triphenylphosphoranyl)propanoate|CS-0536253
      2689-62-5
    • ~97%
    • In-stock
      Methyl 2-(triphenylphosphoranylidene)propanoate|CS-0030442
      2605-68-7

    References

    • Elemes, Yiannis; Foote, Christopher S. Journal of the American Chemical Society, 1992 , vol. 114, # 15 p. 6044 - 6050
  • Route2
    • null|null
      56904-90-6
    • ~99%
    • In-stock
      Methyl 2-(triphenylphosphoranylidene)propanoate|CS-0030442
      2605-68-7

    References

    • Werkhoven, Thekla M.; Van Nispen, Reinier; Lugtenburg, Johan European Journal of Organic Chemistry, 1999 , # 11 p. 2909 - 2914
  • Route3
    • null|null
      603-35-0
    • ~%
    • In-stock
      Methyl 2-(triphenylphosphoranylidene)propanoate|CS-0030442
      2605-68-7

    References

    • Eey, Stanley T.-C.; Lear, Martin J. Organic Letters, 2010 , vol. 12, # 23 p. 5510 - 5513

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   26.3
  • LogP   3.3458
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   4

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