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CS-W001157 4
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1-Bromo-3-methyl-5-nitrobenzene

  • CAS No. 52488-28-5

  • Cat. No. CS-0153266
  • Purity≥97%
  • MDL No.MFCD06659815

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

1-Bromo-3-methyl-5-nitrobenzene|CS-0153266

Structure of 52488-28-5

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General Information

  • CAS No. 52488-28-5
  • Cat. No. CS-0153266
  • Purity ≥97%
  • MDL No. MFCD06659815
  • 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-5-nitrotoluene
  • SMILES CC1=CC(=CC(=C1)[N+](=O)[O-])Br

Description

1-Bromo-3-methyl-5-nitrobenzene features a strategically positioned bromine atom flanked by a methyl group and a nitro substituent, enabling selective cross-coupling reactions. The electron-deficient aromatic ring enhances reactivity in palladium-catalyzed transformations, while the methyl group provides steric stabilization. This compound serves as a key intermediate in synthesizing functionalized aryl scaffolds for pharmaceutical and agrochemical applications.

Application

1-Bromo-3-methyl-5-nitrobenzene 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 bromine atom facilitates efficient C–C bond formation under standard Suzuki, Stille, or Negishi conditions, while the meta-directing nitro group ensures predictable regioselectivity. Its bench-stable nature and compatibility with diverse functional groups make it ideal for multi-step syntheses of complex heterocyclic scaffolds and targeted API intermediates.

Synthesis

  • Route1

    References

    • Procopiou, Panayiotis A.; Barrett, Victoria J.; Ford, Alison J.; Looker, Brian E.; Lunniss, Gillian E.; Needham, Deborah; Smith, Claire E.; Somers, Graham Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 20 p. 6026 - 6032
  • Route2
    • In-stock
      4-Bromo-2-methyl-6-nitroaniline|CS-M1979
      77811-44-0
    • null|null
      6303-21-5
    • ~%
    • In-stock
      1-Bromo-3-methyl-5-nitrobenzene|CS-0153266
      52488-28-5

    References

    • F. HOFFMANN-LA ROCHE AG Patent: EP887346 A2, 1998 ; EP 0887346 A2
  • Route3
    • null|null
      89-62-3
    • ~%
    • In-stock
      1-Bromo-3-methyl-5-nitrobenzene|CS-0153266
      52488-28-5

    References

    • Fisher; Dershem; Prewitt Journal of Organic Chemistry, 1990 , vol. 55, # 3 p. 1040 - 1043

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

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