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CS-W001157 4
Total: USD 88.00

1-(4-Bromo-3-fluorophenyl)cyclopropanecarboxylic acid

  • CAS No. 749269-74-7

  • Cat. No. CS-0054518
  • Purity≥95%
  • MDL No.None

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

1-(4-Bromo-3-fluorophenyl)cyclopropanecarboxylic acid|CS-0054518

Structure of 749269-74-7

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General Information

  • CAS No. 749269-74-7
  • Cat. No. CS-0054518
  • Purity ≥95%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈BrFO₂
  • Molecular Weight 259.07
  • Synonym(s) 1-(4-Bromo-3-fluorophenyl)cyclopropane-1-carboxylic acid
  • SMILES O=C(C1(C2=CC=C(Br)C(F)=C2)CC1)O

Description

This cyclopropanecarboxylic acid features a 4-bromo-3-fluorophenyl substituent, delivering enhanced metabolic stability and favorable lipophilicity for medicinal chemistry applications. The strained cyclopropyl ring imparts conformational rigidity, enabling precise spatial orientation in target binding. This derivative integrates readily into bioactive scaffolds requiring electron-deficient aryl motifs.

Application

1-(4-Bromo-3-fluorophenyl)cyclopropanecarboxylic acid serves as a versatile building block for the synthesis of bioactive heterocycles and pharmaceutical intermediates. Its cyclopropane carboxylic acid motif provides structural rigidity and enhanced metabolic stability, while the ortho-bromo and meta-fluoro substituents enable palladium-catalyzed cross-coupling reactions and modulate electronic properties. The carboxylic acid group facilitates direct derivatization or salt formation, supporting purification and handling in multi-step syntheses.

Synthesis

  • Route1

    References

    • Peretto, Ilaria; Radaelli, Stefano; Parini, Carlo; Zandi, Michele; Raveglia, Luca F.; Dondio, Giulio; Fontanella, Laura; Misiano, Paola; Bigogno, Chiara; Rizzi, Andrea; Riccardi, Benedetta; Biscaioli, Marcello; Marchetti, Silvia; Puccini, Paola; Catinella, Silvia; Rondelli, Ivano; Cenacchi, Valentina; Bolzoni, Pier Tonino; Caruso, Paola; Villetti, Gino; Facchinetti, Fabrizio; Del Giudice, Elda; Moretto, Nadia; Imbimbo, Bruno P. Journal of Medicinal Chemistry, 2005 , vol. 48, # 18 p. 5705 - 5720
  • Route2

    References

    • Peretto, Ilaria; Radaelli, Stefano; Parini, Carlo; Zandi, Michele; Raveglia, Luca F.; Dondio, Giulio; Fontanella, Laura; Misiano, Paola; Bigogno, Chiara; Rizzi, Andrea; Riccardi, Benedetta; Biscaioli, Marcello; Marchetti, Silvia; Puccini, Paola; Catinella, Silvia; Rondelli, Ivano; Cenacchi, Valentina; Bolzoni, Pier Tonino; Caruso, Paola; Villetti, Gino; Facchinetti, Fabrizio; Del Giudice, Elda; Moretto, Nadia; Imbimbo, Bruno P. Journal of Medicinal Chemistry, 2005 , vol. 48, # 18 p. 5705 - 5720
  • Route3

    References

    • Peretto, Ilaria; Radaelli, Stefano; Parini, Carlo; Zandi, Michele; Raveglia, Luca F.; Dondio, Giulio; Fontanella, Laura; Misiano, Paola; Bigogno, Chiara; Rizzi, Andrea; Riccardi, Benedetta; Biscaioli, Marcello; Marchetti, Silvia; Puccini, Paola; Catinella, Silvia; Rondelli, Ivano; Cenacchi, Valentina; Bolzoni, Pier Tonino; Caruso, Paola; Villetti, Gino; Facchinetti, Fabrizio; Del Giudice, Elda; Moretto, Nadia; Imbimbo, Bruno P. Journal of Medicinal Chemistry, 2005 , vol. 48, # 18 p. 5705 - 5720

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-P280-P302+P352

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Computational Chemistry Data

  • TPSA   37.3
  • LogP   2.7044
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   2

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