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4-Fluoro-2-hydroxybenzonitrile

  • CAS No. 186590-01-2

  • Cat. No. CS-0044038
  • Purity≥98%
  • MDL No.MFCD13185487

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

4-Fluoro-2-hydroxybenzonitrile|CS-0044038

Structure of 186590-01-2

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General Information

  • CAS No. 186590-01-2
  • Cat. No. CS-0044038
  • Purity ≥98%
  • MDL No. MFCD13185487
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄FNO
  • Molecular Weight 137.11
  • Synonym(s) None
  • SMILES N#CC1=CC=C(F)C=C1O

Description

4-Fluoro-2-hydroxybenzonitrile features a strategically positioned hydroxyl group flanked by electron-withdrawing fluorine and nitrile moieties, enabling robust participation in cross-coupling and electrophilic substitution reactions. This ortho-hydroxylated aromatic scaffold exhibits enhanced reactivity and stability under standard conditions, facilitating efficient integration into complex molecular architectures.

Application

4-Fluoro-2-hydroxybenzonitrile serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the phenolic hydroxyl and nitrile groups. Its ortho-hydroxy and meta-fluoro substitution pattern facilitates regioselective derivatization, including nucleophilic aromatic substitution and transition-metal-catalyzed coupling reactions. The compound exhibits good bench stability and is readily purified by recrystallization, making it well-suited for use in API intermediate synthesis and heterocyclic scaffold construction.

Synthesis

  • Route1

    References

    • BRISTOL-MYERS SQUIBB COMPANY Patent: WO2007/64316 A1, 2007 ; Location in patent: Page/Page column 153 ;

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

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