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5-Bromo-3-methylthiophene-2-carboxylic acid

  • CAS No. 38239-45-1

  • Cat. No. CS-0153627
  • Purity≥97%
  • MDL No.MFCD11040352

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

5-Bromo-3-methylthiophene-2-carboxylic acid|CS-0153627

Structure of 38239-45-1

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General Information

  • CAS No. 38239-45-1
  • Cat. No. CS-0153627
  • Purity ≥97%
  • MDL No. MFCD11040352
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrO₂S
  • Molecular Weight 221.07
  • Synonym(s) 5-BROMO-3-METHYLTHIOPHENE-3-CARBOXYLIC ACID
  • SMILES CC1=C(C(=O)O)SC(=C1)Br

Description

5-Bromo-3-methylthiophene-2-carboxylic acid features a brominated thiophene core with a methyl group at the 3-position and a carboxylic acid at the 2-position, enabling direct incorporation into heterocyclic scaffolds. The electron-deficient bromo substituent facilitates cross-coupling reactions, while the carboxylic acid group provides a versatile handle for amide formation or metal chelation. This structure offers enhanced solubility in organic media and stability under standard bench conditions, supporting efficient use in medicinal chemistry and materials synthesis workflows.

Application

5-Bromo-3-methylthiophene-2-carboxylic acid serves as a versatile building block for the synthesis of substituted thiophenes and heterocyclic scaffolds. Its bromo and carboxylic acid functionalities enable direct coupling reactions, including Suzuki-Miyaura and Stille couplings, and facilitate derivatization via amide or ester formation. The molecule exhibits good bench stability and compatibility with standard purification techniques, making it well-suited for iterative synthetic workflows in medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • AGOURON PHARMACEUTICALS, INC. Patent: US2004/266796 A1, 2004 ; Location in patent: Page 13 ;
  • Route2

    References

    • NOVARTIS AG; XENON PHARMACEUTICALS INC. Patent: WO2008/74835 A1, 2008 ; Location in patent: Page/Page column 78 ; WO 2008/074835 A1
  • Route3
    • 5-Bromo-3-methylthiophene-2-carbaldehyde|CS-0451922
      38239-46-2
    • ~%
    • In-stock
      5-Bromo-3-methylthiophene-2-carboxylic acid|CS-0153627
      38239-45-1

    References

    • FibroGen, Inc. Patent: US2006/199836 A1, 2006 ; Location in patent: Page/Page column 22 ; US 20060199836 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

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Computational Chemistry Data

  • TPSA   37.3
  • LogP   2.51722
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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