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3,5-Dimethyl-1H-pyrrole-2-carboxylic acid

  • CAS No. 4513-93-3

  • Cat. No. CS-0153631
  • Purity≥95%
  • MDL No.MFCD02681967

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

3,5-Dimethyl-1H-pyrrole-2-carboxylic acid|CS-0153631

Structure of 4513-93-3

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General Information

  • CAS No. 4513-93-3
  • Cat. No. CS-0153631
  • Purity ≥95%
  • MDL No. MFCD02681967
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₉NO₂
  • Molecular Weight 139.15
  • Synonym(s) BUTTPARK 36\18-24
  • SMILES CC1=C(C(=O)O)NC(=C1)C

Description

3,5-Dimethyl-1H-pyrrole-2-carboxylic acid features a sterically hindered pyrrole core with electron-rich character, enabling selective coupling reactions. The carboxylic acid group provides a robust handle for amide bond formation, while the methyl substituents enhance stability and solubility under standard conditions. This scaffold integrates readily into bioactive molecule design.

Application

3,5-Dimethyl-1H-pyrrole-2-carboxylic acid serves as a versatile building block in medicinal chemistry, enabling the synthesis of substituted pyrrole scaffolds via standard coupling reactions. Its carboxylic acid functionality facilitates amide bond formation, while the electron-rich pyrrole core supports electrophilic substitution and transition-metal-catalyzed transformations. The methyl groups at C3 and C5 enhance metabolic stability and provide steric control, contributing to improved solubility and handling characteristics during bench-scale synthesis.

Synthesis

  • Route1

    References

    • Clark, Benjamin R.; O'Connor, Stephen; Fox, Deirdre; Leroy, Jacques; Murphy, Cormac D. Organic and Biomolecular Chemistry, 2011 , vol. 9, # 18 p. 6306 - 6311
  • Route2
    • benZyl 3,5-dimethylpyrrole-2-carboxylate|CS-0235754
      40236-19-9
    • ~99%
    • In-stock
      3,5-Dimethyl-1H-pyrrole-2-carboxylic acid|CS-0153631
      4513-93-3

    References

    • Yon-Hin, Paul; Ian Scott Tetrahedron Letters, 1991 , vol. 32, # 34 p. 4231 - 4234
  • Route3
    • null|null
      15719-64-9
    • ~%
    • In-stock
      3,5-Dimethyl-1H-pyrrole-2-carboxylic acid|CS-0153631
      4513-93-3

    References

    • Fischer; Weiss; Schubert Chemische Berichte, 1923 , vol. 56, p. 1198

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   53.09
  • LogP   1.32974
  • H_Acceptors   1
  • H_Donors   2
  • Rotatable_Bonds   1

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