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CS-W001157 4
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4-Bromobenzo[b]thiophene-2-carboxylic acid

  • CAS No. 5194-37-6

  • Cat. No. CS-0041386
  • Purity≥97%
  • MDL No.MFCD03407342

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

4-Bromobenzo[b]thiophene-2-carboxylic acid|CS-0041386

Structure of 5194-37-6

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General Information

  • CAS No. 5194-37-6
  • Cat. No. CS-0041386
  • Purity ≥97%
  • MDL No. MFCD03407342
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₅BrO₂S
  • Molecular Weight None
  • Synonym(s) Benzo[b]thiophene-2-carboxylic acid, 4-bromo-
  • SMILES O=C(C1=CC2=C(Br)C=CC=C2S1)O

Description

4-Bromobenzo[b]thiophene-2-carboxylic acid features a fused heterocyclic core with a bromine substituent at the benzo position and a carboxylic acid group at the thiophene ring's 2-position. This combination delivers enhanced electronic modulation and synthetic versatility, enabling direct incorporation into cross-coupling reactions and pharmaceutical scaffolds. The molecule exhibits robust stability under standard bench conditions and facilitates efficient derivatization in medicinal chemistry workflows.

Application

4-Bromobenzo[b]thiophene-2-carboxylic acid serves as a versatile building block for the synthesis of biologically active heterocycles and pharmaceutical intermediates. Its bromine and carboxylic acid functionalities enable direct coupling reactions via Pd-catalyzed cross-coupling and derivatization to amides, esters, or acyl chlorides. The benzo[b]thiophene core provides structural rigidity and favorable pharmacokinetic properties, while the molecule exhibits good bench stability and ease of purification, facilitating integration into standard synthetic workflows.

Synthesis

  • Route1
    • In-stock
      2-Bromo-6-fluorobenzaldehyde|CS-D1749
      360575-28-6
    • null|null
      68-11-1
    • ~76%
    • In-stock
      4-Bromobenzo[b]thiophene-2-carboxylic acid|CS-0041386
      5194-37-6

    References

    • ELI LILLY AND COMPANY Patent: WO2007/92751 A2, 2007 ; Location in patent: Page/Page column 20 ;
  • Route2

    References

    • Kissei Pharmaceutical Co., Ltd. Patent: EP1724277 A1, 2006 ; Location in patent: Page/Page column 28-29 ;
  • Route3

    References

    • Sharma, K. S.; Lata, Suman Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1984 , vol. 23, # 1 p. 38 - 41

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-H312-H332
Precautionary Statements : P260-P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P304+P341-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362+P364-P363-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   37.3
  • LogP   3.362
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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