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CS-W001157 4
Total: USD 88.00

3-Bromo-5-nitroanisole

  • CAS No. 16618-67-0

  • Cat. No. CS-M0503
  • Purity≥98%
  • MDL No.MFCD04112752

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

3-Bromo-5-nitroanisole|CS-M0503

Structure of 16618-67-0

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General Information

  • CAS No. 16618-67-0
  • Cat. No. CS-M0503
  • Purity ≥98%
  • MDL No. MFCD04112752
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BrNO₃
  • Molecular Weight 232.03
  • Synonym(s) 1-Bromo-3-methoxy-5-nitrobenzene
  • SMILES BrC1=CC([N+]([O-])=O)=CC(OC)=C1

Description

3-Bromo-5-nitroanisole features a bromine atom flanked by a nitro group and a methoxy substituent on the aromatic ring, enabling selective cross-coupling reactions. This electronic configuration enhances reactivity in palladium-catalyzed transformations while maintaining stability under standard bench conditions.

Application

3-Bromo-5-nitroanisole serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal reactivity profile. The bromo group facilitates reliable C–C bond formation, while the nitro and methoxy functionalities provide predictable electronic modulation and compatibility with standard protecting group strategies. Its bench-stable nature and ease of purification support efficient downstream transformations in multi-step syntheses.

Synthesis

  • Route1
    • null|null
      67-56-1
    • In-stock
      1-bromo-3,5-dinitro-Benzene|CS-M0502
      18242-39-2
    • null|null
      124-41-4
    • ~80%
    • In-stock
      3-Bromo-5-nitroanisole|CS-M0503
      16618-67-0

    References

    • INCYTE CORPORATION Patent: US2009/286778 A1, 2009 ; Location in patent: Page/Page column 84 ; US 20090286778 A1
  • Route2

    References

    • US6458935 B1, ; US 6458935 B1
  • Route3
    • In-stock
      1-bromo-3,5-dinitro-Benzene|CS-M0502
      18242-39-2
    • null|null
      124-41-4
    • ~79%
    • In-stock
      3-Bromo-5-nitroanisole|CS-M0503
      16618-67-0

    References

    • Miroshnikova, Olga V.; Hudson, Thomas H.; Gerena, Lucia; Kyle, Dennis E.; Lin, Ai J. Journal of Medicinal Chemistry, 2007 , vol. 50, # 4 p. 889 - 896

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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