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CS-W001157 4
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4'-Bromo-[1,1'-biphenyl]-4-carboxylic acid

  • CAS No. 5731-11-3

  • Cat. No. CS-0033739
  • Purity≥95%
  • MDL No.MFCD00452920

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

4'-Bromo-[1,1'-biphenyl]-4-carboxylic acid|CS-0033739

Structure of 5731-11-3

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General Information

  • CAS No. 5731-11-3
  • Cat. No. CS-0033739
  • Purity ≥95%
  • MDL No. MFCD00452920
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₉BrO₂
  • Molecular Weight 277.11
  • Synonym(s) Bromo biphenyl carboxylic acid
  • SMILES O=C(C1=CC=C(C2=CC=C(Br)C=C2)C=C1)O

Description

4'-Bromo-[1,1'-biphenyl]-4-carboxylic acid features a brominated aryl moiety paired with a carboxylic acid group, enabling direct coupling in Suzuki-Miyaura and other transition-metal-catalyzed reactions. The para-substituted biphenyl scaffold ensures planarity and enhanced stability, while the terminal carboxylic acid facilitates derivatization under standard conditions. This compound serves as a robust building block for functionalized biaryls in materials science and medicinal chemistry applications.

Application

4'-Bromo-[1,1'-biphenyl]-4-carboxylic acid serves as a versatile building block for constructing biaryl scaffolds in medicinal chemistry and materials science. Its bromo and carboxylic acid functionalities enable sequential cross-coupling reactions and derivatization under standard conditions. The compound exhibits good bench stability and facilitates efficient purification via recrystallization, making it well-suited for scalable synthesis and library generation.

Synthesis

  • Route1

    References

    • Kayani, Zohra N.; Lewis, Robert A.; Naseem, Shahzad Journal of Molecular Liquids, 2012 , vol. 175, p. 72 - 84
  • Route2
    • null|null
      84337-85-9
    • ~86%
    • In-stock
      4'-Bromo-[1,1'-biphenyl]-4-carboxylic acid|CS-0033739
      5731-11-3

    References

    • Boehringer Ingelheim International GmbH Patent: US2004/242572 A1, 2004 ; Location in patent: Page/Page column 94 ;
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    References

    • Simoni, Daniele; Giannini, Giuseppe; Roberti, Marinella; Rondanin, Riccardo; Baruchello, Riccardo; Rossi, Marcello; Grisolia, Giuseppina; Invidiata, Francesco Paolo; Aiello, Stefania; Marino, Silvia; Cavallini, Sabrina; Siniscalchi, Anna; Gebbia, Nicola; Crosta, Lucia; Grimaudo, Stefania; Abbadessa, Vincenzo; Di Cristina, Antonietta; Tolomeo, Manlio Journal of Medicinal Chemistry, 2005 , vol. 48, # 13 p. 4293 - 4299

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P501

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Computational Chemistry Data

  • TPSA   37.3
  • LogP   3.8143
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   2

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