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CS-W001157 4
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5-Bromothiophene-3-carboxamide

  • CAS No. 189329-94-0

  • Cat. No. CS-W007257
  • Purity≥97%
  • MDL No.MFCD11644062

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

5-Bromothiophene-3-carboxamide|CS-W007257

Structure of 189329-94-0

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General Information

  • CAS No. 189329-94-0
  • Cat. No. CS-W007257
  • Purity ≥97%
  • MDL No. MFCD11644062
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄BrNOS
  • Molecular Weight 206.06
  • Synonym(s) 5-bromo-thiophene-3-carboxylic acid amide
  • SMILES O=C(N)C1=CSC(Br)=C1

Description

5-Bromothiophene-3-carboxamide features a brominated thiophene core paired with a carboxamide group, enabling direct integration into cross-coupling and cyclization reactions. The electron-deficient heterocycle facilitates nucleophilic substitution, while the amide moiety offers hydrogen-bonding capacity and enhanced solubility in polar solvents. This structure supports efficient derivatization in medicinal chemistry and materials science applications.

Application

5-Bromothiophene-3-carboxamide serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions due to its bromine substituent and carboxamide functionality. The molecule exhibits good bench stability and facilitates the construction of functionalized thiophene scaffolds common in pharmaceutical intermediates and agrochemicals. Its orthogonal reactivity supports sequential transformations in complex molecule synthesis.

Synthesis

  • Route1

    References

    • Campaigne; Bourgeois Journal of the American Chemical Society, 1954 , vol. 76, p. 2445
  • Route2

    References

    • Campaigne; Bourgeois Journal of the American Chemical Society, 1954 , vol. 76, p. 2445
  • Route3
    • 5-Bromothiophene-3-carbonitrile|CS-0050553
      18792-00-2
    • ~%
    • In-stock
      5-Bromothiophene-3-carboxamide|CS-W007257
      189329-94-0

    References

    • Fournari,P. et al. Bulletin de la Societe Chimique de France, 1967 , p. 4115 - 4120

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

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