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CS-W001157 4
Total: USD 88.00

Methyl 2-acetamido-2-(dimethoxyphosphoryl)acetate

  • CAS No. 89524-99-2

  • Cat. No. CS-0090957
  • Purity≥96%
  • MDL No.MFCD08443722

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

Methyl 2-acetamido-2-(dimethoxyphosphoryl)acetate|CS-0090957

Structure of 89524-99-2

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General Information

  • CAS No. 89524-99-2
  • Cat. No. CS-0090957
  • Purity ≥96%
  • MDL No. MFCD08443722
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₄NO₆P
  • Molecular Weight 239.16
  • Synonym(s) Trimethyl α-(Acetamido)phosphonoacetate
  • SMILES O=C(OC)C(NC(C)=O)P(OC)(OC)=O

Description

Methyl 2-acetamido-2-(dimethoxyphosphoryl)acetate features a phosphonate ester group flanked by an acetamido function, enabling direct incorporation into peptide-like architectures. This bench-stable reagent facilitates efficient P–C bond formation under mild conditions, offering high functional group tolerance and compatibility with diverse synthetic transformations in medicinal chemistry workflows.

Application

Methyl 2-acetamido-2-(dimethoxyphosphoryl)acetate serves as a versatile building block for the synthesis of phosphoramidate prodrugs and phosphorylated heterocycles. Its dimethoxyphosphoryl group enables efficient P–N bond formation, while the acetamido and ester functionalities offer orthogonal reactivity. The compound exhibits bench stability and facilitates straightforward purification, making it well-suited for iterative synthetic sequences in medicinal chemistry and nucleoside analog development.

Synthesis

  • Route1
    • null|null
      108-24-7
    • null|null
      100945-15-1
    • ~90%
    • In-stock
      Methyl 2-acetamido-2-(dimethoxyphosphoryl)acetate|CS-0090957
      89524-99-2

    References

    • Synthesis, , # 1 p. 53 - 60
  • Route2
    • null|null
      73198-56-8
    • null|null
      121-45-9
    • ~42%
    • In-stock
      Methyl 2-acetamido-2-(dimethoxyphosphoryl)acetate|CS-0090957
      89524-99-2

    References

    • US2007/197429 A1, ; Page/Page column 56 ;
  • Route3
    • null|null
      126484-84-2
    • null|null
      121-45-9
    • ~96%
    • In-stock
      Methyl 2-acetamido-2-(dimethoxyphosphoryl)acetate|CS-0090957
      89524-99-2

    References

    • Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , # 12 p. 1603 - 1610

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-H312-H315-H319-H332-H335
Precautionary Statements : P261-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   90.93
  • LogP   0.1075
  • H_Acceptors   6
  • H_Donors   1
  • Rotatable_Bonds   5

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