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CS-W001157 4
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Dimethyl 2-(methoxymethylene)malonate

  • CAS No. 22398-14-7

  • Cat. No. CS-0119967
  • Molecule weight174.15
  • Purity≥97%
  • MDL No.MFCD00038225

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

Dimethyl 2-(methoxymethylene)malonate|CS-0119967

Structure of 22398-14-7

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General Information

  • CAS No. 22398-14-7
  • Cat. No. CS-0119967
  • Purity ≥97%
  • MDL No. MFCD00038225
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₀O₅
  • Molecular Weight 174.15
  • Synonym(s) Methoxymethylenemalonic Acid Dimethyl Ester
  • SMILES O=C(OC)/C(C(OC)=O)=C\OC

Description

Dimethyl 2-(methoxymethylene)malonate features a highly reactive methoxymethylene group flanked by two ester functionalities, enabling efficient participation in [4+2] cycloadditions and Mannich-type reactions. This electron-deficient dienophile integrates readily into synthetic sequences requiring controlled C–C bond formation under mild conditions.

Application

Dimethyl 2-(methoxymethylene)malonate serves as a versatile synthon in heterocyclic synthesis, enabling efficient construction of pyrrolidine and furan scaffolds via condensation and cycloaddition reactions. Its stabilized enolizable methoxymethylene group facilitates controlled Michael additions and Knoevenagel-type condensations, while the dimethyl malonate framework provides excellent functional group tolerance and bench stability. The compound is particularly useful in medicinal chemistry for accessing bioactive core structures with predictable reactivity profiles.

Synthesis

  • Route1
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    • In-stock
      Dimethyl 2-(methoxymethylene)malonate|CS-0119967
      22398-14-7

    References

    • US4665218 A1, ;
  • Route2
    • null|null
      99366-49-1
    • ~0%
    • In-stock
      Dimethyl 2-(methoxymethylene)malonate|CS-0119967
      22398-14-7
    • null|null
      99366-53-7
    • null|null
      104286-66-0

    References

    • Abdallah, Hassan; Gree, Rene; Carrie, Robert Tetrahedron, 1985 , vol. 41, # 19 p. 4339 - 4346
  • Route3
    • In-stock
      Dimethyl malonate|CS-0019394
      108-59-8
    • null|null
      149-73-5
    • ~%
    • In-stock
      Dimethyl 2-(methoxymethylene)malonate|CS-0119967
      22398-14-7

    References

    • Justus Liebigs Annalen der Chemie, , vol. 297, p. 5,78 Chemical and Pharmaceutical Bulletin, , vol. 34, # 11 p. 4875 - 4878

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
Precautionary Statements : P264-P270-P280-P302+P352-P330-P362+P364-P501

Quality Control

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Computational Chemistry Data

  • TPSA   61.83
  • LogP   -0.1373
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   3

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