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CS-W001157 4
Total: USD 88.00

4-Cyano-3-fluorophenylboronic acid

  • CAS No. 843663-18-3

  • Cat. No. CS-M1589
  • Purity≥95%
  • MDL No.MFCD03411549

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

4-Cyano-3-fluorophenylboronic acid|CS-M1589

Structure of 843663-18-3

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General Information

  • CAS No. 843663-18-3
  • Cat. No. CS-M1589
  • Purity ≥95%
  • MDL No. MFCD03411549
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BFNO₂
  • Molecular Weight 164.93
  • Synonym(s) Boronic acid, B-(4-cyano-3-fluorophenyl)-
  • SMILES FC1=CC(B(O)O)=CC=C1C#N

Description

4-Cyano-3-fluorophenylboronic acid features a boronic acid group flanked by electron-withdrawing cyano and fluorine substituents, enhancing its stability and reactivity in Suzuki-Miyaura coupling. This combination enables efficient cross-coupling under mild conditions, delivering arylated products with high fidelity. The molecule's bench-stable nature simplifies handling in synthetic workflows.

Application

4-Cyano-3-fluorophenylboronic acid serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient C–C bond formation under standard Suzuki-Miyaura conditions. The ortho-fluoro and cyano groups provide enhanced reactivity and stability, facilitating selective functionalization in complex molecule synthesis. Its bench-stable solid form simplifies handling and purification, making it ideal for medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • null|null
      121-43-7
    • In-stock
      4-Bromo-2-fluorobenzonitrile|CS-W007363
      105942-08-3
    • ~%
    • In-stock
      4-Cyano-3-fluorophenylboronic acid|CS-M1589
      843663-18-3

    References

    • US2009/291956 A1, ; Page/Page column 25; 26 ;
  • Route2
    • null|null
      5419-55-6
    • In-stock
      4-Bromo-2-fluorobenzonitrile|CS-W007363
      105942-08-3
    • ~69%
    • In-stock
      4-Cyano-3-fluorophenylboronic acid|CS-M1589
      843663-18-3

    References

    • ELI LILLY AND COMPANY Patent: WO2007/87488 A2, 2007 ; Location in patent: Page/Page column 17; 47-48 ;
  • Route3

    References

    • Wang, Xiao-Jun; Sun, Xiufeng; Zhang, Li; Xu, Yibo; Krishnamurthy, Dhileepkumar; Senanayake, Chris H. Organic Letters, 2006 , vol. 8, # 2 p. 305 - 307

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

Quality Control

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Computational Chemistry Data

  • TPSA   64.25
  • LogP   -0.62282
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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