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CS-W001157 4
Total: USD 88.00

2-(Phenylmethylene)butanedioic acid

  • CAS No. 5653-88-3

  • Cat. No. CS-0100988
  • Purity≥97%
  • MDL No.MFCD03090765

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

2-(Phenylmethylene)butanedioic acid|CS-0100988

Structure of 5653-88-3

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General Information

  • CAS No. 5653-88-3
  • Cat. No. CS-0100988
  • Purity ≥97%
  • MDL No. MFCD03090765
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₀O₄
  • Molecular Weight 206.19
  • Synonym(s) butanedioic acid, 2-(phenylmethylene)-, (2E)-
  • SMILES O=C(O)/C(CC(O)=O)=C\C1=CC=CC=C1

Description

This malonate derivative features a phenylmethylene group integrated at the C2 position, enhancing conjugation and electronic delocalization. The molecule combines a rigid aromatic moiety with a reactive dicarboxylic acid core, enabling efficient coupling in synthetic transformations. Its stability under standard conditions supports use in multistep syntheses and modular derivatization workflows.

Application

2-(Phenylmethylene)butanedioic acid serves as a versatile diacid building block for the synthesis of heterocyclic scaffolds and bioactive molecules. Its conjugated enone-like system enables Diels-Alder cycloadditions and Michael additions, while the carboxylic acid groups facilitate derivatization and metal coordination. The compound exhibits good bench stability and is amenable to purification via recrystallization, making it well-suited for use in iterative synthetic sequences and medicinal chemistry campaigns.

Synthesis

  • Route1

    References

    • US6133454 A1, ;
  • Route2

    References

    • US5268361 A1, ; US 5268361 A
  • Route3
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    • In-stock
      2-(Phenylmethylene)butanedioic acid|CS-0100988
      5653-88-3

    References

    • Journal of Medicinal Chemistry, , vol. 36, # 10 p. 1369 - 1379

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-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   74.6
  • LogP   1.6293
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   4

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