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Ethyl 3-formyl-1H-pyrrole-2-carboxylate

  • CAS No. 36131-43-8

  • Cat. No. CS-W022672
  • Purity≥98%
  • MDL No.MFCD13178593

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

Ethyl 3-formyl-1H-pyrrole-2-carboxylate|CS-W022672

Structure of 36131-43-8

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General Information

  • CAS No. 36131-43-8
  • Cat. No. CS-W022672
  • Purity ≥98%
  • MDL No. MFCD13178593
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₉NO₃
  • Molecular Weight 167.16
  • Synonym(s) 1H-Pyrrole-2-carboxylic acid, 3-formyl-, ethyl ester
  • SMILES CCOC(=O)C1=C(C=O)C=CN1

Description

Ethyl 3-formyl-1H-pyrrole-2-carboxylate features a pyrrole core bearing both formyl and ester functionalities, enabling direct integration into heterocyclic synthesis. The electron-deficient pyrrole ring facilitates nucleophilic addition, while the formyl group serves as a key handle for C–C bond formation via aldol or Wittig reactions. This bench-stable reagent streamlines access to complex nitrogen-containing architectures in medicinal chemistry and materials science.

Application

Ethyl 3-formyl-1H-pyrrole-2-carboxylate serves as a versatile heterocyclic building block for constructing biologically relevant scaffolds. The conjugated formyl and ester groups enable sequential functionalization, facilitating nucleophilic additions, condensation reactions, and transition-metal-catalyzed couplings. Its bench-stable nature and compatibility with common protecting group strategies make it ideal for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Liu, Jianquan; Fang, Zhongxue; Zhang, Qian; Liu, Qun; Bi, Xihe Angewandte Chemie - International Edition, 2013 , vol. 52, # 27 p. 6953 - 6957 Angew. Chem., 2013 , vol. 125, # 27 p. 7091 - 7095,5
  • Route2

    References

    • Klose, Walter; Nickisch, Klaus; Bohlmann, Ferdinand Chemische Berichte, 1980 , vol. 113, # 8 p. 2694 - 2698

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

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Computational Chemistry Data

  • TPSA   59.16
  • LogP   1.0039
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   3

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