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CS-W001157 4
Total: USD 88.00

Diethyl (PhthaliMidoMethyl)phosphonate

  • CAS No. 33512-26-4

  • Cat. No. CS-0128375
  • Purity≥97%
  • MDL No.MFCD00134313

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

Diethyl (PhthaliMidoMethyl)phosphonate|CS-0128375

Structure of 33512-26-4

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General Information

  • CAS No. 33512-26-4
  • Cat. No. CS-0128375
  • Purity ≥97%
  • MDL No. MFCD00134313
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₆NO₅P
  • Molecular Weight 297.24
  • Synonym(s) (Phthalimidomethyl)phosphonic Acid Diethyl Ester
  • SMILES O=C(N1CP(OCC)(OCC)=O)C2=CC=CC=C2C1=O

Description

Diethyl (phthalimidomethyl)phosphonate features a phosphonate group tethered to a phthalimide-bearing methylene linker, enabling direct incorporation into heterocyclic scaffolds. This stable, moisture-tolerant reagent facilitates efficient P–C bond formation in synthetic sequences requiring nitrogen-anchored phosphonates.

Application

Diethyl (phthalimidomethyl)phosphonate serves as a versatile synthon for the construction of phosphonate-containing heterocycles and bioactive scaffolds. Its phthalimide-protected amine moiety enables selective deprotection and functionalization, while the phosphonate group facilitates C–C bond formation via Horner–Wadsworth–Emmons or related olefination reactions. The compound exhibits excellent bench stability, ease of handling, and compatibility with common protecting group strategies, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • In-stock
      2-(Bromomethyl)isoindoline-1,3-dione|CS-0063420
      5332-26-3
    • null|null
      122-52-1
    • ~98%
    • In-stock
      Diethyl (PhthaliMidoMethyl)phosphonate|CS-0128375
      33512-26-4

    References

    • Gao, Jian; Guo, Yang Hui; Wang, Ya Ping; Wang, Xiang Jing; Xiang, Wen Sheng Chinese Chemical Letters, 2011 , vol. 22, # 10 p. 1159 - 1162
  • Route2
    • In-stock
      1-[bromomethyl(ethoxy)phosphoryl]oxyethane|CS-0061667
      66197-72-6
    • 2-(Tert-butyldimethylsilyl)isoindoline-1,3-dione|CS-0535143
      79293-84-8
    • ~87%
    • In-stock
      Diethyl (PhthaliMidoMethyl)phosphonate|CS-0128375
      33512-26-4

    References

    • Chun; Park; Oh; Hong; Kim Synthesis, 1994 , # 9 p. 909 - 910
  • Route3
    • null|null
      136918-14-4
    • In-stock
      Diethyl (hydroxymethyl)phosphonate|CS-W017818
      3084-40-0
    • ~62%
    • In-stock
      Diethyl (PhthaliMidoMethyl)phosphonate|CS-0128375
      33512-26-4

    References

    • Baraldi, P. G.; Guarneri, M.; Moroder, F.; Pollini, G. P.; Simoni, D. Synthesis, 1982 , # 8 p. 653 - 655

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   72.91
  • LogP   2.5062
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   6

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