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CS-W001157 4
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5-Bromo-1,3-difluoro-2-nitrobenzene

  • CAS No. 147808-42-2

  • Cat. No. CS-W009157
  • Purity≥98%
  • MDL No.MFCD12025434

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

5-Bromo-1,3-difluoro-2-nitrobenzene|CS-W009157

Structure of 147808-42-2

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General Information

  • CAS No. 147808-42-2
  • Cat. No. CS-W009157
  • Purity ≥98%
  • MDL No. MFCD12025434
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₂BrF₂NO₂
  • Molecular Weight 237.99
  • Synonym(s) benzene, 5-bromo-1,3-difluoro-2-nitro-
  • SMILES O=[N+](C1=C(F)C=C(Br)C=C1F)[O-]

Description

5-Bromo-1,3-difluoro-2-nitrobenzene features a trifunctional aromatic core with complementary reactivity for cross-coupling and nucleophilic substitution. The electron-deficient ring facilitates efficient palladium-catalyzed transformations, while the bromo and nitro groups enable sequential functionalization. This compound serves as a versatile intermediate in pharmaceutical synthesis and agrochemical development under standard conditions.

Application

5-Bromo-1,3-difluoro-2-nitrobenzene serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling palladium-catalyzed cross-coupling reactions due to its ortho-bromine substitution. The nitro group facilitates subsequent reduction and functionalization, while the difluoro substitution enhances metabolic stability and modulates electronic properties. Its bench-stable nature and compatibility with standard reaction conditions make it well-suited for multi-step synthetic sequences.

Synthesis

  • Route1

    References

    • Rueeger, Heinrich; Lueoend, Rainer; Rogel, Olivier; Rondeau, Jean-Michel; Moebitz, Henrik; MacHauer, Rainer; Jacobson, Laura; Staufenbiel, Matthias; Desrayaud, Sandrine; Neumann, Ulf Journal of Medicinal Chemistry, 2012 , vol. 55, # 7 p. 3364 - 3386
  • Route2
    • 3,5-Difluoro-4-nitroaniline|CS-0106865
      122129-79-7
    • ~%
    • In-stock
      5-Bromo-1,3-difluoro-2-nitrobenzene|CS-W009157
      147808-42-2

    References

    • Journal of Organic Chemistry USSR (English Translation), , vol. 28, # 7 p. 1140 - 1147 Zhurnal Organicheskoi Khimii, , vol. 28, # 7 p. 1445 - 1454

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   43.14
  • LogP   2.6355
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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