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CS-W001157 4
Total: USD 88.00

2-Bromo-5-nitroanisole

  • CAS No. 77337-82-7

  • Cat. No. CS-W014685
  • Purity≥97%
  • MDL No.MFCD00041250

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

2-Bromo-5-nitroanisole|CS-W014685

Structure of 77337-82-7

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General Information

  • CAS No. 77337-82-7
  • Cat. No. CS-W014685
  • Purity ≥97%
  • MDL No. MFCD00041250
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BrNO₃
  • Molecular Weight 232.03
  • Synonym(s) 4-Bromo-3-methoxynitrobenzene; 2-Bromo-5-nitroanisole
  • SMILES COC1=CC([N+]([O-])=O)=CC=C1Br

Description

2-Bromo-5-nitroanisole features a bromine atom and a nitro group positioned ortho to a methoxy substituent on the aromatic ring, creating a highly functionalized platform for cross-coupling reactions. This electron-deficient aryl halide integrates seamlessly into palladium-catalyzed transformations, enabling efficient access to complex heterocycles and pharmaceutical intermediates under standard conditions.

Application

2-Bromo-5-nitroanisole serves as a versatile building block in cross-coupling reactions, enabling efficient construction of biaryl and heterocyclic scaffolds. Its bromine and nitro groups provide orthogonal reactivity for Pd-catalyzed coupling and selective reduction, while the methoxy group enhances solubility and stability. The compound exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • null|null
      97-52-9
    • ~92%
    • In-stock
      2-Bromo-5-nitroanisole|CS-W014685
      77337-82-7

    References

    • Tetrahedron, , vol. 69, # 16 p. 3511 - 3517
  • Route2
    • In-stock
      2-Bromo-5-nitrophenol|CS-W008085
      52427-05-1
    • null|null
      74-88-4
    • ~94%
    • In-stock
      2-Bromo-5-nitroanisole|CS-W014685
      77337-82-7

    References

    • Journal of the American Chemical Society, , vol. 134, # 2 p. 1104 - 1114
  • Route3
    • null|null
      186581-53-3
    • In-stock
      2-Bromo-5-nitrophenol|CS-W008085
      52427-05-1
    • ~89%
    • In-stock
      2-Bromo-5-nitroanisole|CS-W014685
      77337-82-7

    References

    • Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , p. 2456 - 2463

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   52.37
  • LogP   2.3659
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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