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CS-W001157 4
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3-Bromobenzo[b]thiophene-2-carbaldehyde

  • CAS No. 10135-00-9

  • Cat. No. CS-0193950
  • Purity≥98%
  • MDL No.None

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

3-Bromobenzo[b]thiophene-2-carbaldehyde|CS-0193950

Structure of 10135-00-9

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General Information

  • CAS No. 10135-00-9
  • Cat. No. CS-0193950
  • Purity ≥98%
  • MDL No. None
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅BrOS
  • Molecular Weight 241.10
  • Synonym(s) 3-BROMOBENZOTHIOPHENE-2-CARBOXALDEHYDE
  • SMILES C1=CC=C2C(=C1)C(=C(C=O)S2)Br

Description

3-Bromobenzo[b]thiophene-2-carbaldehyde features a brominated benzo[b]thiophene core with an aldehyde group at the 2-position, enabling direct functionalization in cross-coupling and multistep synthesis. The electron-deficient thiophene ring enhances reactivity in transition-metal catalyzed transformations. This bench-stable compound serves as a key scaffold for heterocyclic building blocks in medicinal chemistry and materials science.

Application

3-Bromobenzo[b]thiophene-2-carbaldehyde serves as a versatile building block for heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal reactivity profile. The aldehyde functionality facilitates efficient derivatization via oxidation, reduction, or nucleophilic addition, while the bromine atom supports further functionalization through standard Suzuki, Stille, or Negishi coupling protocols. Bench-stable and readily purified by flash chromatography, it functions effectively in medicinal chemistry campaigns requiring fused thiophene scaffolds with tunable substitution patterns.

Synthesis

  • Route1
    • In-stock
      3-Bromobenzo[b]thiophene|CS-W005311
      7342-82-7
    • null|null
      68-12-2
    • ~90%
    • In-stock
      3-Bromobenzo[b]thiophene-2-carbaldehyde|CS-0193950
      10135-00-9

    References

    • Zhao, Hang; Dankwardt, John W.; Koenig, Stefan G.; Singh, Surendra P. Tetrahedron Letters, 2012 , vol. 53, # 2 p. 166 - 169
  • Route2
    • In-stock
      2,3-Dibromobenzo[b]thiophene|CS-W005898
      6287-82-7
    • null|null
      68-12-2
    • ~91%
    • In-stock
      3-Bromobenzo[b]thiophene-2-carbaldehyde|CS-0193950
      10135-00-9

    References

    • Bjoerk, Malin; Grivas, Spiros Journal of Heterocyclic Chemistry, 2006 , vol. 43, # 1 p. 101 - 109
  • Route3
    • In-stock
      Benzo[b]thiophen-3(2H)-one|CS-W003457
      130-03-0
    • null|null
      68-12-2
    • ~92%
    • In-stock
      3-Bromobenzo[b]thiophene-2-carbaldehyde|CS-0193950
      10135-00-9

    References

    • Kirsch, Gilbert; Deprets, Stephanie Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2006 , vol. 61, # 4 p. 427 - 430

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H319
Precautionary Statements : P264-P270-P280-P330-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   3.4763
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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