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CS-W001157 4
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Ethyl 5-bromothiophene-2-carboxylate

  • CAS No. 5751-83-7

  • Cat. No. CS-W002964
  • Purity≥96%
  • MDL No.MFCD02683089

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

Ethyl 5-bromothiophene-2-carboxylate|CS-W002964

Structure of 5751-83-7

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General Information

  • CAS No. 5751-83-7
  • Cat. No. CS-W002964
  • Purity ≥96%
  • MDL No. MFCD02683089
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₇BrO₂S
  • Molecular Weight 235.10
  • Synonym(s) Ethyl 5-bromo-2-thiophenecarboxylate
  • SMILES CCOC(=O)c1ccc(s1)Br

Description

Ethyl 5-bromothiophene-2-carboxylate is a bench-stable, moisture-tolerant building block featuring a brominated thiophene core. This electrophilic heterocycle integrates readily into cross-coupling reactions, enabling efficient access to functionalized thienyl architectures for materials science and pharmaceutical applications.

Application

Ethyl 5-bromothiophene-2-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions for the construction of biologically relevant thiophene-containing scaffolds. The bromine substituent provides high reactivity in Suzuki, Stille, and Negishi couplings, while the ester group offers compatibility with standard functional group manipulations. Its bench stability and ease of purification facilitate integration into multi-step synthetic sequences.

Synthesis

  • Route1

    References

    • ARROW THERAPEUTICS LIMITED Patent: WO2009/34390 A1, 2009 ; Location in patent: Page/Page column 28 ; WO 2009/034390 A1
  • Route2
    • null|null
      3141-27-3
    • In-stock
      Ethyl carbonocyanidate|CS-0022374
      623-49-4
    • ~76%
    • In-stock
      Ethyl 5-bromothiophene-2-carboxylate|CS-W002964
      5751-83-7

    References

    • Abarbri, Mohamed; Dehmel, Florian; Knochel, Paul Tetrahedron Letters, 1999 , vol. 40, # 42 p. 7449 - 7453
  • Route3

    References

    • US4923884 A1, ;

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   26.3
  • LogP   2.6873
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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