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4-Bromo-3-methylthiophene-2-carboxylic acid

  • CAS No. 265652-39-9

  • Cat. No. CS-0068006
  • Purity≥98%
  • MDL No.MFCD03789231

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

4-Bromo-3-methylthiophene-2-carboxylic acid|CS-0068006

Structure of 265652-39-9

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General Information

  • CAS No. 265652-39-9
  • Cat. No. CS-0068006
  • Purity ≥98%
  • MDL No. MFCD03789231
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrO₂S
  • Molecular Weight 221.07
  • Synonym(s) 4-Bromo-3-methylthiophenecarboxylic acid
  • SMILES O=C(C1=C(C)C(Br)=CS1)O

Description

4-Bromo-3-methylthiophene-2-carboxylic acid features a thiophene core with strategically positioned bromine and methyl groups, enabling direct functionalization in cross-coupling reactions. The carboxylic acid moiety provides a handle for derivatization, while the electron-deficient nature of the ring enhances reactivity in palladium-catalyzed transformations. This compound serves as a key building block in the synthesis of bioactive heterocycles and advanced materials.

Application

4-Bromo-3-methylthiophene-2-carboxylic acid serves as a versatile building block for the synthesis of bioactive heterocycles and pharmaceutical intermediates. Its bromine and carboxylic acid functionalities enable direct coupling reactions via Pd-catalyzed cross-coupling and amide formation, while the methylthiophene core provides structural rigidity and tunable electronic properties. The compound exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for scalable medicinal chemistry campaigns and process development.

Synthesis

  • Route1
    • 2,4-Dibromo-3-methylthiophene|CS-0612208
      53119-66-7
    • ~%
    • In-stock
      4-Bromo-3-methylthiophene-2-carboxylic acid|CS-0068006
      265652-39-9

    References

    • Steinkopf; Jacob Justus Liebigs Annalen der Chemie, 1935 , vol. 515, p. 273,277

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H319
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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