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CS-W001157 4
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3-Fluoro-2-nitrophenol

  • CAS No. 385-01-3

  • Cat. No. CS-W007764
  • Purity≥97%
  • MDL No.MFCD07368753

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

3-Fluoro-2-nitrophenol|CS-W007764

Structure of 385-01-3

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General Information

  • CAS No. 385-01-3
  • Cat. No. CS-W007764
  • Purity ≥97%
  • MDL No. MFCD07368753
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₄FNO₃
  • Molecular Weight 157.10
  • Synonym(s) 2-nitro-3-fluorophenol
  • SMILES FC1=C([N+]([O-])=O)C(O)=CC=C1

Description

3-Fluoro-2-nitrophenol features a fluorine atom ortho to a nitro group on a phenolic scaffold, creating a strongly electron-deficient aromatic system. This configuration enhances reactivity in nucleophilic substitution and enables selective functionalization under mild conditions. The compound exhibits bench-stable handling characteristics and integrates readily into synthetic routes targeting bioactive heterocycles and advanced pharmaceutical intermediates.

Application

3-Fluoro-2-nitrophenol serves as a versatile building block in synthetic organic chemistry, enabling direct functionalization of electron-deficient aromatic systems. Its ortho-nitro and fluoro substituents facilitate subsequent coupling reactions, including palladium-catalyzed cross-couplings and nucleophilic aromatic substitutions. The compound exhibits good bench stability and is readily purified by recrystallization, making it suitable for use in the synthesis of heterocyclic scaffolds and pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • BOEHRINGER INGELHEIM PHARMACEUTICALS, INC. Patent: WO2005/30213 A1, 2005 ; Location in patent: Page/Page column 182-183 ; WO 2005/030213 A1
  • Route2

    References

    • Skaddan, Marc B.; Bergman, Robert G. Journal of Labelled Compounds and Radiopharmaceuticals, 2006 , vol. 49, # 7 p. 623 - 634
  • Route3

    References

    • Betageri, Raj; Gilmore, Thomas; Kuzmich, Daniel; Kirrane, Thomas M.; Bentzien, Joerg; Wiedenmayer, Dieter; Bekkali, Younes; Regan, John; Berry, Angela; Latli, Bachir; Kukulka, Alison J.; Fadra, Tazmeen N.; Nelson, Richard M.; Goldrick, Susan; Zuvela-Jelaska, Ljiljana; Souza, Don; Pelletier, Josephine; Dinallo, Roger; Panzenbeck, Mark; Torcellini, Carol; Lee, Heewon; Pack, Edward; Harcken, Christian; Nabozny, Gerald; Thomson, David S. Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 22 p. 6842 - 6851

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07,GHS09
Signal Word : Danger
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H302-H315-H317-H318-H410
Precautionary Statements : P261-P264-P270-P272-P273-P280-P302+P352-P330-P362+P364-P391-P501

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Computational Chemistry Data

  • TPSA   63.37
  • LogP   1.4395
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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