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Methyl 3-bromobenzo[b]thiophene-2-carboxylate

  • CAS No. 34128-30-8

  • Cat. No. CS-0565673
  • Purity≥98%
  • MDL No.None

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

Methyl 3-bromobenzo[b]thiophene-2-carboxylate|CS-0565673

Structure of 34128-30-8

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General Information

  • CAS No. 34128-30-8
  • Cat. No. CS-0565673
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₇BrO₂S
  • Molecular Weight 271.13
  • Synonym(s) methyl 3-bromobenzothiophene-2-carboxylate
  • SMILES O=C(C1=C(Br)C2=CC=CC=C2S1)OC

Description

Methyl 3-bromobenzo[b]thiophene-2-carboxylate is a bench-stable, moisture-tolerant heterocyclic building block featuring a brominated thiophene core. This electron-deficient scaffold enables direct functionalization via palladium-catalyzed cross-coupling, streamlining access to complex fused-ring architectures in medicinal chemistry and materials science applications.

Application

Methyl 3-bromobenzo[b]thiophene-2-carboxylate serves as a versatile building block for the synthesis of biologically relevant heterocycles, enabling palladium-catalyzed cross-coupling reactions at the bromine site. The methyl ester group offers straightforward functionalization via hydrolysis or reduction, while the benzo[b]thiophene core provides robust scaffold stability and π-conjugation beneficial in medicinal chemistry applications. Its bench-stable nature and compatibility with standard reaction conditions make it well-suited for iterative synthetic workflows.

Synthesis

  • Route1

    References

    • Iaroshenko, Viktor O.; Ali, Sajid; Mkrtchyan, Satenik; Gevorgyan, Ashot; Babar, Tariq Mahmood; Semeniuchenko, Volodymyr; Hassan, Zahid; Villinger, Alexander; Langer, Peter Tetrahedron Letters, 2012 , vol. 53, # 52 p. 7135 - 7139
  • Route2
    • null|null
      67-56-1
    • In-stock
      3-Bromo-1-benzothiophene-2-carboxylic acid|CS-0215053
      29174-66-1
    • ~95%
    • In-stock
      Methyl 3-bromobenzo[b]thiophene-2-carboxylate|CS-0565673
      34128-30-8

    References

    • Zborovskii, Yu. L.; Smirnov-Zamkov, I. V.; Staninets, V. I. Journal of Organic Chemistry USSR (English Translation), 1984 , p. 1617 - 1625 Zhurnal Organicheskoi Khimii, 1984 , vol. 20, # 8 p. 1774 - 1784
  • Route3
    • In-stock
      3-Bromo-1-benzothiophene-2-carboxylic acid|CS-0215053
      29174-66-1
    • null|null
      18107-18-1
    • ~99%
    • In-stock
      Methyl 3-bromobenzo[b]thiophene-2-carboxylate|CS-0565673
      34128-30-8

    References

    • Dydio, Pawel; Reek, Joost N. H. Angewandte Chemie - International Edition, 2013 , vol. 52, # 14 p. 3878 - 3882 Angew. Chem., 2013 , vol. 125, # 14 p. 4132

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   26.3
  • LogP   3.4504
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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