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Ethyl 4-(diethoxyphosphoryl)butanoate

  • CAS No. 2327-69-7

  • Cat. No. CS-0128907
  • Molecule weight252.24
  • Purity≥98%
  • MDL No.MFCD00015168

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

Ethyl 4-(diethoxyphosphoryl)butanoate|CS-0128907

Structure of 2327-69-7

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General Information

  • CAS No. 2327-69-7
  • Cat. No. CS-0128907
  • Purity ≥98%
  • MDL No. MFCD00015168
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₂₁O₅P
  • Molecular Weight 252.24
  • Synonym(s) Triethyl 4-phosphonobutyrate
  • SMILES O=C(OCC)CCCP(OCC)(OCC)=O

Description

Ethyl 4-(diethoxyphosphoryl)butanoate features a reactive phosphonate ester group flanked by a flexible aliphatic chain, enabling efficient coupling in Pudovin-type reactions. This bench-stable reagent integrates readily into synthetic sequences requiring controlled C–C bond formation, offering high functional group tolerance and straightforward handling under standard conditions.

Application

Ethyl 4-(diethoxyphosphoryl)butanoate serves as a versatile synthon in carbonyl-alkylation and Michael addition strategies, enabling efficient construction of γ- and δ-functionalized carboxylates. Its diethylphosphoryl group facilitates nucleophilic displacement and acts as a masked acyl equivalent, while the ester functionality supports orthogonal transformations. Bench-stable and readily purified by distillation, it functions reliably in standard synthetic workflows for complex molecule assembly.

Synthesis

  • Route1

    References

    • Ponaire, Sarah; Zingle, Catherine; Tritsch, Denis; Grosdemange-Billiard, Catherine; Rohmer, Michel European Journal of Medicinal Chemistry, 2012 , vol. 51, p. 277 - 285
  • Route2

    References

    • Wasielewski, Czeslaw; Antczak, Kazimierz Synthesis, 1981 , # 7 p. 540 - 541
  • Route3
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      96-48-0
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      122-52-1
    • ~%
    • Ethyl 4-(diethoxyphosphoryl)butanoate|CS-0128907
      2327-69-7

    References

    • Journal of the American Chemical Society, , vol. 78, p. 4450

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P280-P302+P352-P362

Quality Control

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Computational Chemistry Data

  • TPSA   61.83
  • LogP   2.5958
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   9

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