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CS-W001157 4
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4-Fluoro-2-nitrobenzonitrile

  • CAS No. 80517-21-1

  • Cat. No. CS-W002604
  • Purity≥96%
  • MDL No.MFCD00277447

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

4-Fluoro-2-nitrobenzonitrile|CS-W002604

Structure of 80517-21-1

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General Information

  • CAS No. 80517-21-1
  • Cat. No. CS-W002604
  • Purity ≥96%
  • MDL No. MFCD00277447
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₃FN₂O₂
  • Molecular Weight 166.11
  • Synonym(s) 2-Cyano-5-fluoronitrobenzene
  • SMILES N#Cc1ccc(cc1[N+](=O)[O-])F

Description

4-Fluoro-2-nitrobenzonitrile features a fluorine atom at the para position relative to the nitrile group, enhancing electrophilicity and enabling selective functionalization. The ortho-nitro group imparts strong electron-withdrawing character, facilitating nucleophilic aromatic substitution under mild conditions. This compound serves as a key building block in the synthesis of bioactive heterocycles and advanced pharmaceutical intermediates.

Application

4-Fluoro-2-nitrobenzonitrile serves as a versatile building block in medicinal chemistry, enabling efficient construction of substituted benzimidazoles and other heterocyclic scaffolds. Its orthogonal reactivity—combining electrophilic fluorine, nitro, and nitrile groups—facilitates sequential functionalization under mild conditions. The compound exhibits excellent bench stability and is readily purified by recrystallization, making it well-suited for scale-up and multi-step synthesis workflows.

Synthesis

  • Route1

    References

    • Sasson, Yoel; Negussie, Samuel; Royz, Michael; Mushkin, Noam Chemical Communications, 1996 , # 3 p. 297 - 298
  • Route2

    References

    • Collection of Czechoslovak Chemical Communications, , vol. 51, # 3 p. 698 - 722
  • Route3

    References

    • Collection of Czechoslovak Chemical Communications, , vol. 51, # 3 p. 698 - 722

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 3439
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301+H311+H331-H315-H319-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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