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1,2,3-Trifluoro-5-nitrobenzene

  • CAS No. 66684-58-0

  • Cat. No. CS-D1418
  • Purity≥98%
  • MDL No.MFCD00456803

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

1,2,3-Trifluoro-5-nitrobenzene|CS-D1418

Structure of 66684-58-0

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General Information

  • CAS No. 66684-58-0
  • Cat. No. CS-D1418
  • Purity ≥98%
  • MDL No. MFCD00456803
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₂F₃NO₂
  • Molecular Weight 177.08
  • Synonym(s) 3,4,5-Trifluoro-1-nitrobenzene; 3,4,5-Trifluoronitrobenzene
  • SMILES O=[N+](C1=CC(F)=C(F)C(F)=C1)[O-]

Description

1,2,3-Trifluoro-5-nitrobenzene features a highly electron-deficient aromatic ring due to the synergistic effect of three fluorine atoms and a para-nitro group. This combination enhances reactivity in nucleophilic aromatic substitution, enabling efficient coupling under mild conditions. The molecule exhibits excellent bench stability and moisture tolerance, simplifying handling in synthetic workflows.

Application

1,2,3-Trifluoro-5-nitrobenzene serves as a versatile building block in medicinal chemistry and materials science, enabling direct electrophilic substitution or transition-metal-catalyzed coupling reactions. The electron-deficient aromatic core exhibits enhanced reactivity in Suzuki-Miyaura and Buchwald-Hartwig couplings, while the nitro group provides a handle for selective reduction or further functionalization. Bench-stable and compatible with common protecting groups, it facilitates efficient synthesis of fluorinated heterocycles and advanced pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • DR. REDDY'S LABORATORIES LTD. Patent: WO2004/37765 A1, 2004 ; Location in patent: Page 7; 8-9 ;
  • Route2

    References

    • WO2003/106450 A1, ; Page column 59,60 ; WO 03/106450 A1
  • Route3

    References

    • Advanced Synthesis and Catalysis, , vol. 354, # 8 p. 1529 - 1541

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2810
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H227-H300
Precautionary Statements : P210-P264-P270-P280-P330-P370+P378-P405-P501

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Computational Chemistry Data

  • TPSA   43.14
  • LogP   2.0121
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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