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4-(Bromomethyl)-2-fluoro-1-nitrobenzene

  • CAS No. 131858-37-2

  • Cat. No. CS-0463100
  • Purity≥97%
  • MDL No.MFCD03094237

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

4-(Bromomethyl)-2-fluoro-1-nitrobenzene|CS-0463100

Structure of 131858-37-2

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General Information

  • CAS No. 131858-37-2
  • Cat. No. CS-0463100
  • Purity ≥97%
  • MDL No. MFCD03094237
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅BrFNO₂
  • Molecular Weight 234.02
  • Synonym(s) 3-Fluoro-4-nitrobenzyl bromide
  • SMILES C1=CC(=C(C=C1CBr)F)[N+](=O)[O-]

Description

4-(Bromomethyl)-2-fluoro-1-nitrobenzene features a reactive bromomethyl group flanked by electron-withdrawing fluorine and nitro substituents, enabling efficient coupling in cross-coupling and bioconjugation workflows. The ortho-fluoro substitution enhances regioselectivity, while the bench-stable aryl halide resists premature decomposition under standard conditions.

Application

4-(Bromomethyl)-2-fluoro-1-nitrobenzene serves as a versatile bifunctional building block for C–C and C–heteroatom bond formation. The bromomethyl group enables palladium-catalyzed cross-coupling reactions, while the ortho-fluoro and para-nitro substituents provide orthogonal reactivity for selective functionalization. Its bench-stable nature and compatibility with common protecting groups facilitate efficient synthesis of complex aryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Beugelmans, Rene; Gonzalez Zamora, Eduardo; Roussi, Georges Tetrahedron Letters, 1997 , vol. 38, # 47 p. 8189 - 8192
  • Route2

    References

    • ABBOTT LABORATORIES Patent: WO2009/39135 A1, 2009 ; Location in patent: Page/Page column 110-111 ;

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

Quality Control

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Computational Chemistry Data

  • TPSA   43.14
  • LogP   2.6288
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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