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CS-W001157 4
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2-Fluoro-4-(hydroxymethyl)benzonitrile

  • CAS No. 222978-02-1

  • Cat. No. CS-W005493
  • Purity≥95%
  • MDL No.MFCD08236861

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

2-Fluoro-4-(hydroxymethyl)benzonitrile|CS-W005493

Structure of 222978-02-1

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General Information

  • CAS No. 222978-02-1
  • Cat. No. CS-W005493
  • Purity ≥95%
  • MDL No. MFCD08236861
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆FNO
  • Molecular Weight 151.14
  • Synonym(s) None
  • SMILES N#CC1=CC=C(CO)C=C1F

Description

2-Fluoro-4-(hydroxymethyl)benzonitrile features a strategically positioned nitrile group and fluorinated aromatic ring, enabling integration into bioactive scaffolds. The hydroxymethyl functionality offers a handle for derivatization, while the electron-withdrawing nitrile enhances metabolic stability. This compound serves as a key building block in medicinal chemistry for targeted molecular design.

Application

2-Fluoro-4-(hydroxymethyl)benzonitrile serves as a versatile building block for medicinal chemistry and heterocyclic synthesis. The nitrile group enables efficient transformations to amides, carboxylic acids, or amidines, while the hydroxymethyl moiety supports oxidation, protection, or coupling reactions. Fluorine substitution enhances metabolic stability and modulates electronic properties. This compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for scalable synthesis workflows in API development.

Synthesis

  • Route1
    • null|null
      433939-83-4
    • ~81%
    • In-stock
      2-Fluoro-4-(hydroxymethyl)benzonitrile|CS-W005493
      222978-02-1

    References

    • ASTRAZENECA AB Patent: WO2003/101956 A1, 2003 ; Location in patent: Page 127 ; WO 03/101956 A1
  • Route2

    References

    • US2003/87940 A1, ;
  • Route3
    • null|null
      557-21-1
    • In-stock
      (4-Bromo-3-fluorophenyl)methanol|CS-W010488
      222978-01-0
    • ~72%
    • In-stock
      2-Fluoro-4-(hydroxymethyl)benzonitrile|CS-W005493
      222978-02-1

    References

    • DeSolms, S. Jane; Ciccarone, Terrence M.; MacTough, Suzanne C.; Shaw, Anthony W.; Buser, Carolyn A.; Ellis-Hutchings, Michelle; Fernandes, Christine; Hamilton, Kelly A.; Huber, Hans E.; Kohl, Nancy E.; Lobell, Robert B.; Robinson, Ronald G.; Tsou, Nancy N.; Walsh, Eileen S.; Graham, Samuel L.; Beese, Lorena S.; Taylor, Jeffrey S. Journal of Medicinal Chemistry, 2003 , vol. 46, # 14 p. 2973 - 2984

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   1.18968
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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