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Methyl 3-bromothiophene-2-carboxylate

  • CAS No. 26137-08-6

  • Cat. No. CS-W002470
  • Purity≥98%
  • MDL No.MFCD00173839

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

Methyl 3-bromothiophene-2-carboxylate|CS-W002470

Structure of 26137-08-6

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General Information

  • CAS No. 26137-08-6
  • Cat. No. CS-W002470
  • Purity ≥98%
  • MDL No. MFCD00173839
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrO₂S
  • Molecular Weight 221.07
  • Synonym(s) 3-Bromothiophene-2-carboxylic Acid Methyl Ester
  • SMILES COC(=O)c1sccc1Br

Description

Methyl 3-bromothiophene-2-carboxylate is a bench-stable, moisture-tolerant heterocyclic building block featuring a brominated thiophene core. This electron-deficient scaffold integrates readily into cross-coupling reactions, enabling efficient access to functionalized thienyl architectures in medicinal chemistry and materials science applications.

Application

Methyl 3-bromothiophene-2-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its well-established bromo functionality. The methyl ester group offers facile manipulation via hydrolysis or reduction, while the thiophene core provides robust stability and compatibility with diverse reaction conditions. This compound facilitates efficient access to functionalized thiophene scaffolds relevant to pharmaceutical and agrochemical development.

Synthesis

  • Route1

    References

    • Tetrahedron Letters, , vol. 53, # 52 p. 7135 - 7139
  • Route2
    • null|null
      67-56-1
    • In-stock
      3-Bromothiophene-2-carboxylic acid|CS-W004773
      7311-64-0
    • ~99%
    • In-stock
      Methyl 3-bromothiophene-2-carboxylate|CS-W002470
      26137-08-6

    References

    • WO2009/79352 A1, ; Page/Page column 63 ; WO 2009/079352 A1
  • Route3

    References

    • Archiv der Pharmazie, , vol. 331, # 12 p. 405 - 411

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   2.2972
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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