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1-(M-tolyl)-1H-pyrrole-2,5-dione

  • CAS No. 20299-79-0

  • Cat. No. CS-0318328
  • Purity≥97%
  • MDL No.MFCD00047117

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

1-(M-tolyl)-1H-pyrrole-2,5-dione|CS-0318328

Structure of 20299-79-0

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General Information

  • CAS No. 20299-79-0
  • Cat. No. CS-0318328
  • Purity ≥97%
  • MDL No. MFCD00047117
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₉NO₂
  • Molecular Weight 187.19
  • Synonym(s) 1-(3-Methylphenyl)-1h-pyrrole-2,5-dione
  • SMILES CC1=CC(=CC=C1)N2C(=O)C=CC2=O

Description

1-(M-tolyl)-1H-pyrrole-2,5-dione features a sterically hindered pyrrolone core fused with a meta-substituted phenyl ring, delivering enhanced stability and tunable electronic properties. This electron-deficient heterocycle integrates readily into conjugated systems, enabling efficient coupling in synthetic transformations. Its bench-stable nature supports reliable handling under standard conditions.

Application

1-(M-tolyl)-1H-pyrrole-2,5-dione serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted pyrroles and heterocyclic scaffolds. Its electron-deficient dienophile character facilitates reliable Diels-Alder reactions with dienes, while the ortho-methyl group provides steric and electronic modulation for downstream functionalization. Bench-stable and readily purified by recrystallization, it functions effectively in multi-step synthesis workflows requiring predictable reactivity and compatibility with common protecting groups.

Synthesis

  • Route1
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      108-31-6
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      108-44-1
    • ~%
    • In-stock
      1-(M-tolyl)-1H-pyrrole-2,5-dione|CS-0318328
      20299-79-0

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 20, # 9 p. 2876 - 2879
  • Route2
    • (Z)-4-oxo-4-(m-tolylamino)but-2-enoic acid|CS-0327366
      42537-50-8
    • ~%
    • In-stock
      1-(M-tolyl)-1H-pyrrole-2,5-dione|CS-0318328
      20299-79-0

    References

    • Journal of the Chemical Society. Perkin Transactions 2, , # 9 p. 1611 - 1619
  • Route3
    • null|null
      54012-55-4
    • ~%
    • In-stock
      1-(M-tolyl)-1H-pyrrole-2,5-dione|CS-0318328
      20299-79-0

    References

    • US2444536 , ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H400
Precautionary Statements : P264-P270-P273-P330-P391-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   37.38
  • LogP   1.42442
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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