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CS-W001157 4
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1-Bromo-3-methyl-2-nitrobenzene

  • CAS No. 52414-97-8

  • Cat. No. CS-0053875
  • Purity≥98%
  • MDL No.None

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

1-Bromo-3-methyl-2-nitrobenzene|CS-0053875

Structure of 52414-97-8

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General Information

  • CAS No. 52414-97-8
  • Cat. No. CS-0053875
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆BrNO₂
  • Molecular Weight 216.03
  • Synonym(s) 3-Bromo-2-nitrotoluene
  • SMILES O=[N+](C1=C(C)C=CC=C1Br)[O-]

Description

1-Bromo-3-methyl-2-nitrobenzene features a strategically positioned bromine atom adjacent to a methyl group and flanked by a nitro substituent, enabling selective cross-coupling reactions. This electron-deficient aryl halide exhibits enhanced reactivity in palladium-catalyzed transformations, offering efficient access to complex substituted arenes under standard conditions.

Application

1-Bromo-3-methyl-2-nitrobenzene serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling palladium-catalyzed cross-coupling reactions due to its reactive aryl bromide moiety. The ortho-nitro group provides strong electron-withdrawing character, enhancing electrophilicity for nucleophilic aromatic substitution. Its bench-stable nature and compatibility with standard functional group transformations make it ideal for constructing complex heterocyclic scaffolds and multi-functionalized aromatic systems.

Synthesis

  • Route1

    References

    • Cournoyer, Richard Leo; Loughhead, David Garrett; O'Yang, Counde Patent: US2004/110815 A1, 2004 ; Location in patent: Page/Page column 18 ; US 20040110815 A1
  • Route2
    • null|null
      540-80-7
    • In-stock
      3-Methyl-2-nitroaniline|CS-W021963
      601-87-6
    • ~58%
    • In-stock
      1-Bromo-3-methyl-2-nitrobenzene|CS-0053875
      52414-97-8

    References

    • F. HOFFMANN-LA ROCHE AG Patent: WO2005/16892 A1, 2005 ; Location in patent: Page/Page column 68 ; WO 2005/016892 A1
  • Route3
    • null|null
      591-17-3
    • ~%
    • In-stock
      1-Bromo-3-methyl-2-nitrobenzene|CS-0053875
      52414-97-8

    References

    • Geerling; Wibaut Recueil des Travaux Chimiques des Pays-Bas, 1934 , vol. 53, p. 1011,1016, 1025

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   43.14
  • LogP   2.66572
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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