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5-Bromothiophene-2-carboxamide

  • CAS No. 76371-66-9

  • Cat. No. CS-W015353
  • Purity≥96%
  • MDL No.MFCD01922020

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

5-Bromothiophene-2-carboxamide|CS-W015353

Structure of 76371-66-9

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General Information

  • CAS No. 76371-66-9
  • Cat. No. CS-W015353
  • Purity ≥96%
  • MDL No. MFCD01922020
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄BrNOS
  • Molecular Weight 206.06
  • Synonym(s) 2-bromo-5-carbamoylthiophene
  • SMILES O=C(C1=CC=C(Br)S1)N

Description

5-Bromothiophene-2-carboxamide features a brominated thiophene core fused to a carboxamide group, offering a versatile scaffold for medicinal chemistry. The electron-deficient heterocycle enables efficient coupling reactions, while the amide functionality enhances solubility and target engagement in kinase inhibitors and other bioactive molecules. This compound serves as a key intermediate in the synthesis of functionalized heterocycles.

Application

5-Bromothiophene-2-carboxamide serves as a versatile building block in synthetic organic chemistry, enabling direct functionalization at the thiophene ring and amide handle. Its bromine substituent facilitates palladium-catalyzed cross-coupling reactions, while the carboxamide group offers stability and polarity advantageous for purification and downstream derivatization. This compound functions effectively in the construction of bioactive heterocycles and pharmaceutical scaffolds under standard reaction conditions.

Synthesis

  • Route1

    References

    • GALAPAGOS N.V. Patent: WO2007/138072 A2, 2007 ; Location in patent: Page/Page column 48 ;
  • Route2

    References

    • Wang, Gao; Yu, Qing-Ying; Chen, Shan-Yong; Yu, Xiao-Qi Organic and Biomolecular Chemistry, 2014 , vol. 12, # 3 p. 414 - 417
  • Route3
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      31555-60-9
    • ~%
    • In-stock
      5-Bromothiophene-2-carboxamide|CS-W015353
      76371-66-9

    References

    • Recueil des Travaux Chimiques des Pays-Bas, , vol. 68, p. 5,29

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-H317
Precautionary Statements : P264-P270-P301+P310-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   43.09
  • LogP   1.6095
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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