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CS-W001157 4
Total: USD 88.00

1,5-Difluoro-3-methoxy-2-nitrobenzene

  • CAS No. 66684-61-5

  • Cat. No. CS-0097034
  • Purity≥97%
  • MDL No.MFCD11865203

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

1,5-Difluoro-3-methoxy-2-nitrobenzene|CS-0097034

Structure of 66684-61-5

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General Information

  • CAS No. 66684-61-5
  • Cat. No. CS-0097034
  • Purity ≥97%
  • MDL No. MFCD11865203
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅F₂NO₃
  • Molecular Weight 189.12
  • Synonym(s) 3,5-difluoro-2-nitroanisole
  • SMILES O=[N+]([O-])C1=C(C=C(C=C1F)F)OC

Description

1,5-Difluoro-3-methoxy-2-nitrobenzene features a uniquely activated aromatic core with orthogonal electron-withdrawing fluorine and nitro groups, enabling selective functionalization. The methoxy substituent enhances solubility while stabilizing the electronic profile. This compound serves as a high-performance building block for advanced synthetic intermediates in medicinal chemistry and agrochemical development.

Application

1,5-Difluoro-3-methoxy-2-nitrobenzene serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient construction of substituted heterocycles via palladium-catalyzed cross-coupling reactions. The ortho-difluoro motif facilitates selective functionalization, while the methoxy and nitro groups provide orthogonal reactivity for downstream transformations. Bench-stable and compatible with standard purification methods, it functions effectively in multi-step syntheses requiring high regioselectivity and functional group tolerance.

Synthesis

  • Route1
    • In-stock
      3,5-Difluoro-2-nitrophenol|CS-0036890
      151414-46-9
    • null|null
      74-88-4
    • ~85%
    • In-stock
      1,5-Difluoro-3-methoxy-2-nitrobenzene|CS-0097034
      66684-61-5

    References

    • DAIICHI PHARMACEUTICAL CO., LTD. Patent: EP1346982 A1, 2003 ;
  • Route2

    References

    • Malamas, Michael S.; Ni, Yike; Erdei, James; Stange, Hans; Schindler, Rudolf; Lankau, Hans-Joachim; Grunwald, Christian; Fan, Kristi Yi; Parris, Kevin; Langen, Barbara; Egerland, Ute; Hage, Thorsten; Marquis, Karen L.; Grauer, Steve; Brennan, Julie; Navarra, Rachel; Graf, Radka; Harrison, Boyd L.; Robichaud, Albert; Kronbach, Thomas; Pangalos, Menelas N.; Hoefgen, Norbert; Brandon, Nicholas J. Journal of Medicinal Chemistry, 2011 , vol. 54, # 21 p. 7621 - 7638
  • Route3
    • In-stock
      1,3,5-Trifluoro-2-nitrobenzene|CS-W020685
      315-14-0
    • null|null
      74-88-4
    • ~93%
    • In-stock
      1,5-Difluoro-3-methoxy-2-nitrobenzene|CS-0097034
      66684-61-5

    References

    • SANOFI Patent: US2012/277220 A1, 2012 ; Location in patent: Page/Page column 19 ;

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

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Computational Chemistry Data

  • TPSA   52.37
  • LogP   1.8816
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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