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CS-W001157 4
Total: USD 88.00

Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate

  • CAS No. 46193-76-4

  • Cat. No. CS-W018766
  • Purity≥98%
  • MDL No.MFCD03425800

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

Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate|CS-W018766

Structure of 46193-76-4

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General Information

  • CAS No. 46193-76-4
  • Cat. No. CS-W018766
  • Purity ≥98%
  • MDL No. MFCD03425800
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₉NO₂S
  • Molecular Weight 195.24
  • Synonym(s) Ethyl 4H-Thieno[2,3-d]Pyrrole-5-Carboxylate
  • SMILES CCOC(=O)C1=CC2=C(N1)C=CS2

Description

Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate features a fused thienopyrrole core with enhanced electron-rich character, enabling efficient integration into π-conjugated systems. The ester functionality supports facile derivatization and facilitates purification under standard conditions. This bench-stable heterocycle serves as a key building block for functional materials in organic electronics and synthetic medicinal chemistry.

Application

Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate serves as a versatile heterocyclic building block for synthesizing biologically relevant scaffolds. Its fused thienopyrrole core exhibits robust stability and facilitates palladium-catalyzed cross-coupling reactions. The ester functionality enables straightforward derivatization, while the electron-rich aromatic system supports diverse functional group tolerance, making it well-suited for medicinal chemistry campaigns and process-scale synthesis.

Synthesis

  • Route1
    • In-stock
      2-Thiophenecarboxaldehyde|CS-W013657
      98-03-3
    • null|null
      637-81-0
    • ~50%
    • In-stock
      Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate|CS-W018766
      46193-76-4

    References

    • Jiang, Xin-Dong; Zhang, Houjun; Zhang, Yuanlin; Zhao, Weili Tetrahedron, 2012 , vol. 68, # 47 p. 9795 - 9801,7
  • Route2
    • null|null
      1056976-66-9
    • ~66%
    • In-stock
      Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate|CS-W018766
      46193-76-4

    References

    • AstraZeneca UK Limited Patent: US6479527 B1, 2002 ; US 6479527 B1
  • Route3
    • null|null
      35355-50-1
    • ~93%
    • In-stock
      Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate|CS-W018766
      46193-76-4

    References

    • Wu, Yayang; Cheng, Chi; Jiao, Lijuan; Yu, Changjiang; Wang, Sufan; Wei, Yun; Mu, Xiaolong; Hao, Erhong Organic Letters, 2014 , vol. 16, # 3 p. 748 - 751

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

Quality Control

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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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