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CS-W001157 4
Total: USD 88.00

2-Bromo-3-nitroanisole

  • CAS No. 67853-37-6

  • Cat. No. CS-W001123
  • Purity≥97%
  • MDL No.MFCD07779272

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

2-Bromo-3-nitroanisole|CS-W001123

Structure of 67853-37-6

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General Information

  • CAS No. 67853-37-6
  • Cat. No. CS-W001123
  • Purity ≥97%
  • MDL No. MFCD07779272
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BrNO₃
  • Molecular Weight 232.03
  • Synonym(s) 2-Bromo-3-nitrophenyl methyl ether
  • SMILES O=[N+](C1=C(Br)C(OC)=CC=C1)[O-]

Description

2-Bromo-3-nitroanisole features a strategically positioned bromine atom and nitro group flanking a methoxy-substituted aromatic ring, enabling direct functionalization in cross-coupling reactions. This electron-deficient aryl halide integrates readily into complex molecular architectures under standard conditions.

Application

2-Bromo-3-nitroanisole serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions due to its well-defined halogen functionality. The nitro group provides strong electron-withdrawing character, enhancing reactivity in nucleophilic substitution and facilitating downstream functionalization. Its methoxy substituent offers orthogonal handle for selective transformations, while the molecule exhibits excellent bench stability and ease of purification—making it a reliable intermediate in the synthesis of complex heterocycles and pharmaceutical scaffolds.

Synthesis

  • Route1
    • In-stock
      2-Bromo-3-nitrophenol|CS-W005430
      101935-40-4
    • null|null
      74-88-4
    • ~92%
    • In-stock
      2-Bromo-3-nitroanisole|CS-W001123
      67853-37-6

    References

    • Boehringer Ingelheim International GmbH Patent: US2006/19905 A1, 2006 ; Location in patent: Page/Page column 24 ; US 20060019905 A1
  • Route2

    References

    • Schumacher, Richard; Danca, Mihaela Diana; Ma, Jianguo; Herbert, Brian; Nguyen, True Minh; Xie, Wenge; Tehim, Ashok Patent: US2007/78147 A1, 2007 ; Location in patent: Page/Page column 67 ;
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 49, # 17 p. 5352 - 5362

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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