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CS-W001157 4
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5-Fluoro-2-nitrobenzonitrile

  • CAS No. 50594-78-0

  • Cat. No. CS-W016064
  • Purity≥97%
  • MDL No.MFCD01632196

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

5-Fluoro-2-nitrobenzonitrile|CS-W016064

Structure of 50594-78-0

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General Information

  • CAS No. 50594-78-0
  • Cat. No. CS-W016064
  • Purity ≥97%
  • MDL No. MFCD01632196
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₃FN₂O₂
  • Molecular Weight 166.11
  • Synonym(s) 5-FLUORO-2-NITROBENZONITRIL
  • SMILES N#CC1=CC(F)=CC=C1[N+]([O-])=O

Description

5-Fluoro-2-nitrobenzonitrile features a trifunctional aryl core bearing fluorine, nitro, and nitrile groups in a regioselective arrangement. This electron-deficient scaffold enables direct coupling in cross-coupling reactions and serves as a key intermediate in the synthesis of fluorinated heterocycles and bioactive compounds under standard conditions.

Application

5-Fluoro-2-nitrobenzonitrile serves as a versatile building block in synthetic organic chemistry, enabling efficient access to functionalized aromatic scaffolds. Its ortho-difunctional substitution pattern—combining a nitro group and nitrile with a fluorine atom—facilitates sequential transformations via selective reduction, nucleophilic substitution, or transition-metal-catalyzed coupling. The molecule exhibits excellent bench stability and tolerates a range of reaction conditions, making it well-suited for multi-step synthesis of heterocyclic intermediates and advanced pharmaceutical precursors.

Synthesis

  • Route1

    References

    • JAMES BLACK FOUNDATION Patent: WO2006/129120 A2, 2006 ; Location in patent: Page/Page column 78 ; WO 2006/129120 A2
  • Route2
    • 3-Fluorobenzonitrile Crisaborole  Impurity|CS-0229060
      403-54-3
    • ~87%
    • In-stock
      5-Fluoro-2-nitrobenzonitrile|CS-W016064
      50594-78-0

    References

    • Rohm and Haas Company Patent: US31455 E1, 1983 ;
  • Route3
    • In-stock
      2,4-Difluoro-1-nitrobenzene|CS-W020034
      446-35-5
    • null|null
      143-33-9
    • ~31%
    • In-stock
      5-Fluoro-2-nitrobenzonitrile|CS-W016064
      50594-78-0

    References

    • Quan, Mimi L.; Lam, Patrick Y. S.; Han, Qi; Pinto, Donald J. P.; He, Ming Y.; Li, Renhua; Ellis, Christopher D.; Clark, Charles G.; Teleha, Christopher A.; Sun, Jung-Hui; Alexander, Richard S.; Bai, Steve; Luettgen, Joseph M.; Knabb, Robert M.; Wong, Pancras C.; Wexler, Ruth R. Journal of Medicinal Chemistry, 2005 , vol. 48, # 6 p. 1729 - 1744

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 3439
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H302-H311-H315-H319-H332-H335
Precautionary Statements : P264-P270-P330-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   66.93
  • LogP   1.60558
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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