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CS-W001157 4
Total: USD 88.00

2-Bromo-1-methoxy-4-nitrobenzene

  • CAS No. 5197-28-4

  • Cat. No. CS-0015276
  • Purity≥98%
  • MDL No.MFCD00041242

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

2-Bromo-1-methoxy-4-nitrobenzene|CS-0015276

Structure of 5197-28-4

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General Information

  • CAS No. 5197-28-4
  • Cat. No. CS-0015276
  • Purity ≥98%
  • MDL No. MFCD00041242
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BrNO₃
  • Molecular Weight 232.03
  • Synonym(s) Anisole, 2-bromo-4-nitro-; 2-Bromo-1-methoxy-4-nitrobenzene
  • SMILES O=[N+](C1=CC=C(OC)C(Br)=C1)[O-]

Description

2-Bromo-1-methoxy-4-nitrobenzene features a strategically positioned nitro group and methoxy substituent that enhance electrophilic reactivity while maintaining stability under standard conditions. This ortho-directing brominated scaffold enables efficient coupling in cross-coupling reactions, particularly in palladium-catalyzed transformations where precise regiocontrol is required.

Application

2-Bromo-1-methoxy-4-nitrobenzene serves as a versatile aryl building block for palladium-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl scaffolds. The bromine functionality provides high reactivity in Suzuki, Stille, and Negishi couplings, while the methoxy and nitro groups offer orthogonal handle options for further functionalization. Bench-stable and readily purified by recrystallization, it functions reliably in multi-step synthetic sequences requiring precise regiocontrol.

Synthesis

  • Route1
    • null|null
      100-17-4
    • ~85%
    • In-stock
      2-Bromo-1-methoxy-4-nitrobenzene|CS-0015276
      5197-28-4

    References

    • Bose, Anima; Mal, Prasenjit Tetrahedron Letters, 2014 , vol. 55, # 13 p. 2154 - 2156
  • Route2

    References

    • Baik, Woonphil; Luan, Wanqiang; Lee, Hyun Joo; Yoon, Cheol Hun; Koo, Sangho; Kim, Byeong Hyo Canadian Journal of Chemistry, 2005 , vol. 83, # 3 p. 213 - 219
  • Route3

    References

    • Clewley, Robin G.; Fischer, Alfred; Henderson, George N. Canadian Journal of Chemistry, 1989 , vol. 67, p. 1472 - 1479

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   2.3659
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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