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CS-W001157 4
Total: USD 88.00

2-Bromo-4-methyl-6-nitroaniline

  • CAS No. 827-24-7

  • Cat. No. CS-W021615
  • Purity≥98%
  • MDL No.MFCD00209452

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

2-Bromo-4-methyl-6-nitroaniline|CS-W021615

Structure of 827-24-7

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General Information

  • CAS No. 827-24-7
  • Cat. No. CS-W021615
  • Purity ≥98%
  • MDL No. MFCD00209452
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₇BrN₂O₂
  • Molecular Weight 231.05
  • Synonym(s) 4-Amino-3-bromo-5-nitrotoluene, 2-Bromo-6-nitro-p-toluidine
  • SMILES NC1=C([N+]([O-])=O)C=C(C)C=C1Br

Description

2-Bromo-4-methyl-6-nitroaniline features a nitro group at the para position relative to the amino functionality, conferring strong electron-withdrawing character. The bromine substituent enables direct functionalization via palladium-catalyzed cross-coupling reactions. This bench-stable compound integrates readily into complex heterocyclic scaffolds and serves as a key intermediate in the synthesis of bioactive molecules and advanced materials.

Application

2-Bromo-4-methyl-6-nitroaniline serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted pyridines and quinolines via cyclization protocols. Its bromo and nitro groups provide orthogonal reactivity for palladium-catalyzed coupling and selective reduction, while the methyl group enhances regiochemical control. Bench-stable and amenable to standard purification methods, it functions reliably in multi-step sequences for API and agrochemical intermediates.

Synthesis

  • Route1
    • null|null
      89-62-3
    • ~10%
    • In-stock
      2-Bromo-4-methyl-6-nitroaniline|CS-W021615
      827-24-7

    References

    • Yasui, Yoshizumi; Frantz, Derik K.; Siegel, Jay S. Organic Letters, 2006 , vol. 8, # 22 p. 4989 - 4992
  • Route2

    References

    • Justus Liebigs Annalen der Chemie, , vol. 192, p. 203
  • Route3
    • null|null
      70733-24-3
    • ~%
    • In-stock
      2-Bromo-4-methyl-6-nitroaniline|CS-W021615
      827-24-7

    References

    • Journal of the Chemical Society, , vol. 105, p. 514

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   69.16
  • LogP   2.24792
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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