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CS-W001157 4
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5-Fluoro-2-hydroxybenzonitrile

  • CAS No. 91407-41-9

  • Cat. No. CS-W005093
  • Purity≥95%
  • MDL No.MFCD11846513

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

5-Fluoro-2-hydroxybenzonitrile|CS-W005093

Structure of 91407-41-9

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General Information

  • CAS No. 91407-41-9
  • Cat. No. CS-W005093
  • Purity ≥95%
  • MDL No. MFCD11846513
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄FNO
  • Molecular Weight 137.11
  • Synonym(s) 2-cyano-4-fluorophenol
  • SMILES N#CC1=CC(F)=CC=C1O

Description

5-Fluoro-2-hydroxybenzonitrile features a fluorine atom at the meta position relative to the hydroxyl group, creating a uniquely polarized aromatic system. The para-oriented nitrile and phenolic hydroxyl groups enable strong hydrogen bonding and enhanced solubility in polar solvents. This combination imparts high reactivity in nucleophilic substitution and coupling reactions. The compound exhibits bench-stable behavior under standard conditions and serves as a key intermediate in the synthesis of bioactive heterocycles and functionalized dyes.

Application

5-Fluoro-2-hydroxybenzonitrile serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the phenolic hydroxyl and nitrile groups. Its ortho-substituted architecture facilitates regioselective derivatization, while the fluorine atom enhances metabolic stability and modulates electronic properties. The compound exhibits good bench stability and compatibility with standard coupling and protection protocols, making it suitable for synthesizing bioactive heterocycles and API intermediates.

Synthesis

  • Route1
    • 2-(Benzyloxy)-5-fluorobenzonitrile|CS-0679481
      945614-14-2
    • ~97%
    • In-stock
      5-Fluoro-2-hydroxybenzonitrile|CS-W005093
      91407-41-9

    References

    • ARRAY BIOPHARMA INC.; GRONEBERG, Robert; BURGESS, Laurence, E.; HARVEY, Darren; LAIRD, Ellen; MUNSON, Mark; RIZZI, James; RODRIGUEZ, Martha; EARY, Charles, Todd; WATSON, Daniel Patent: WO2007/89646 A1, 2007 ; Location in patent: Page/Page column 12; 45 ; WO 2007/089646 A1
  • Route2
    • null|null
      91407-40-8
    • ~99%
    • In-stock
      5-Fluoro-2-hydroxybenzonitrile|CS-W005093
      91407-41-9

    References

    • ABBOTT LABORATORIES; LI, Tongmei Patent: WO2005/111003 A1, 2005 ; Location in patent: Page/Page column 131 ; WO 2005/111003 A1
  • Route3

    References

    • Munson, Mark; Kim, Youngboo; Groneberg, Robert D.; Rizzi, James; Rodriguez, Martha; Kim, Ganghyeok; Vigers, Guy; Rao, Chang; Balachari, Devan Patent: US2004/180896 A1, 2004 ; US 20040180896 A1 Title/Abstract Full Text Show Details Munson, Mark; Mareska, David A.; Kim, Youngboo; Groneberg, Robert D.; Rizzi, James; Rodriguez, Martha; Kim, Ganghyeok; Vigers, Guy; Rao, Chang; Balachari, Devan; Harvey, Darren Patent: US2004/192653 A1, 2004 ; US 20040192653 A1

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   44.02
  • LogP   1.40298
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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