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CS-W001157 4
Total: USD 88.00

2-Bromo-1,3-dimethyl-5-nitrobenzene

  • CAS No. 53906-84-6

  • Cat. No. CS-0160016
  • Purity≥95%
  • MDL No.MFCD02178896

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

2-Bromo-1,3-dimethyl-5-nitrobenzene|CS-0160016

Structure of 53906-84-6

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General Information

  • CAS No. 53906-84-6
  • Cat. No. CS-0160016
  • Purity ≥95%
  • MDL No. MFCD02178896
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈BrNO₂
  • Molecular Weight 230.06
  • Synonym(s) None
  • SMILES O=[N+](C1=CC(C)=C(Br)C(C)=C1)[O-]

Description

2-Bromo-1,3-dimethyl-5-nitrobenzene features a strategically positioned bromine atom flanked by two methyl groups and a nitro substituent, enabling selective cross-coupling reactions. This electron-deficient aryl halide integrates efficiently into palladium-catalyzed transformations, offering high reactivity under mild conditions with excellent functional group tolerance.

Application

2-Bromo-1,3-dimethyl-5-nitrobenzene serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling palladium-catalyzed cross-coupling reactions due to its well-defined electronic and steric profile. The bromine substituent facilitates reliable C–C bond formation under standard Suzuki, Stille, or Negishi conditions, while the nitro group provides a handle for selective reduction or further functionalization. Bench-stable and readily purified by recrystallization, it functions efficiently in multi-step syntheses requiring ortho-directed substitution patterns.

Synthesis

  • Route1

    References

    • Spitzer; Wheland Journal of the American Chemical Society, 1940 , vol. 62, p. 2995,3001
  • Route2

    References

    • Kalypsys, Inc. Patent: US2005/234046 A1, 2005 ; Location in patent: Page/Page column 94 ; US 20050234046 A1
  • Route3

    References

    • van Berk et al. Recueil des Travaux Chimiques des Pays-Bas, 1956 , vol. 75, p. 1137,1138, 1149

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   2.97414
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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