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CS-W001157 4
Total: USD 88.00

Diethyl ((phenylsulfonyl)methyl)phosphonate

  • CAS No. 56069-39-7

  • Cat. No. CS-0108760
  • Purity≥97%
  • MDL No.MFCD03453041

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

Diethyl ((phenylsulfonyl)methyl)phosphonate|CS-0108760

Structure of 56069-39-7

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General Information

  • CAS No. 56069-39-7
  • Cat. No. CS-0108760
  • Purity ≥97%
  • MDL No. MFCD03453041
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₇O₅PS
  • Molecular Weight 292.29
  • Synonym(s) Diethyl (phenylsulfonyl) methanephospuonate
  • SMILES O=P(CS(=O)(C1=CC=CC=C1)=O)(OCC)OCC

Description

Diethyl (phenylsulfonyl)methylphosphonate features a phosphonate group flanked by electron-withdrawing phenylsulfonyl and ethoxy substituents, enhancing its reactivity in C–C bond formations. This bench-stable reagent integrates efficiently into Horner–Wadsworth–Emmons reactions, enabling selective olefination of aldehydes with minimal side-product formation.

Application

Diethyl ((phenylsulfonyl)methyl)phosphonate serves as a versatile synthon for the introduction of sulfonylethyl functionality, enabling efficient construction of sulfonamide and sulfonic acid derivatives. Its phosphonate group facilitates Stetter-type reactions and acts as a Michael acceptor in conjugate additions. The phenylsulfonyl moiety enhances stability and aids in purification, making it suitable for bench-scale synthesis of medicinally relevant scaffolds.

Synthesis

  • Route1
    • Diethyl ((phenylthio)methyl)phosphonate|CS-0343253
      38066-16-9
    • ~99%
    • In-stock
      Diethyl ((phenylsulfonyl)methyl)phosphonate|CS-0108760
      56069-39-7

    References

    • Balczewski,Piotr Phosphorus, Sulfur and Silicon and the Related Elements, 1995 , vol. 104, # 14 p. 113 - 122
  • Route2
    • In-stock
      Methyl phenyl sulfone|CS-0011576
      3112-85-4
    • null|null
      814-49-3
    • ~83%
    • In-stock
      Diethyl ((phenylsulfonyl)methyl)phosphonate|CS-0108760
      56069-39-7

    References

    • Stokes, Benjamin J.; Liu, Sheng; Driver, Tom G. Journal of the American Chemical Society, 2011 , vol. 133, # 13 p. 4702 - 4705
  • Route3
    • null|null
      50746-65-1
    • ~80%
    • In-stock
      Diethyl ((phenylsulfonyl)methyl)phosphonate|CS-0108760
      56069-39-7

    References

    • Clare, Brian W.; Ferro, Vito; Skelton, Brian W.; Stick, Robert V.; White, Allan H. Australian Journal of Chemistry, 1993 , vol. 46, # 6 p. 805 - 824

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   69.67
  • LogP   2.6839
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   7

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