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Ethyl 6H-thieno[2,3-b]pyrrole-5-carboxylate

  • CAS No. 35357-56-3

  • Cat. No. CS-0151719
  • Purity≥95%
  • MDL No.MFCD06761694

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

Ethyl 6H-thieno[2,3-b]pyrrole-5-carboxylate|CS-0151719

Structure of 35357-56-3

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General Information

  • CAS No. 35357-56-3
  • Cat. No. CS-0151719
  • Purity ≥95%
  • MDL No. MFCD06761694
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉NO₂S
  • Molecular Weight 195.24
  • Synonym(s) 6H-THIENO[2,3-B]PYRROLE-5-CARBOXYLIC ACID ETHYL ESTER
  • SMILES CCOC(=O)C1=CC2=C(N1)SC=C2

Description

Ethyl 6H-thieno[2,3-b]pyrrole-5-carboxylate features a fused thienopyrrole core with enhanced electron-rich character, enabling efficient integration into donor-acceptor architectures. The ester functionality provides synthetic handle for further derivatization under standard conditions. This bench-stable compound facilitates access to functionalized heterocycles in organic synthesis and materials science applications.

Application

Ethyl 6H-thieno[2,3-b]pyrrole-5-carboxylate serves as a versatile heterocyclic building block for constructing biologically relevant scaffolds. Its fused thienopyrrole core exhibits robust stability and compatibility with standard synthetic transformations. The ester functionality enables facile derivatization via hydrolysis or nucleophilic substitution, while the electron-rich aromatic system supports palladium-catalyzed cross-coupling reactions. This compound functions effectively in medicinal chemistry campaigns requiring access to fused polycyclic systems with tunable electronic properties.

Synthesis

  • Route1
    • null|null
      35355-52-3
    • ~86%
    • In-stock
      Ethyl 6H-thieno[2,3-b]pyrrole-5-carboxylate|CS-0151719
      35357-56-3

    References

    • Eras, J.; Galvez, C.; Garcia, F. Journal of Heterocyclic Chemistry, 1984 , vol. 21, p. 215 - 217
  • Route2
    • null|null
      335030-68-7
    • ~93%
    • In-stock
      Ethyl 6H-thieno[2,3-b]pyrrole-5-carboxylate|CS-0151719
      35357-56-3

    References

    • Affinium Pharmaceuticals, Inc. Patent: EP1226138 B1, 2004 ;
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 48, # 26 p. 8289 - 8298

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-H317
Precautionary Statements : P261-P264-P270-P272-P280-P302+P352-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   42.09
  • LogP   2.4061
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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