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CS-W001157 4
Total: USD 88.00

2-Bromo-3-nitropyridine

  • CAS No. 19755-53-4

  • Cat. No. CS-W015483
  • Purity≥98%
  • MDL No.MFCD00955613

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

2-Bromo-3-nitropyridine|CS-W015483

Structure of 19755-53-4

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General Information

  • CAS No. 19755-53-4
  • Cat. No. CS-W015483
  • Purity ≥98%
  • MDL No. MFCD00955613
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₃BrN₂O₂
  • Molecular Weight 202.99
  • Synonym(s) 2-bromo-3-nitro pyridine; 2-Bromo-3-nitropyridine
  • SMILES O=[N+](C1=CC=CN=C1Br)[O-]

Description

2-Bromo-3-nitropyridine features a strategically positioned bromine and nitro group on the pyridine ring, enabling direct functionalization in cross-coupling and nucleophilic substitution reactions. The electron-deficient heterocycle enhances reactivity toward palladium-catalyzed transformations, while maintaining stability under standard bench conditions.

Application

2-Bromo-3-nitropyridine serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its stable bromine functionality. The nitro group provides a handle for selective reduction and further functionalization, while the pyridine core offers inherent polarity and coordination capability. Its bench stability and compatibility with standard reaction conditions facilitate efficient access to substituted pyridine scaffolds relevant to medicinal chemistry and agrochemical development.

Synthesis

  • Route1

    References

    • Journal of the Chemical Society, , p. 2042,2044
  • Route2

    References

    • Journal of Organic Chemistry, , vol. 77, # 9 p. 4402 - 4413
  • Route3

    References

    • Loidreau, Yvonnick; Marchand, Pascal; Dubouilh-Benard, Carole; Nourrisson, Marie-Renee; Duflos, Muriel; Lozach, Olivier; Loaec, Nadege; Meijer, Laurent; Besson, Thierry European Journal of Medicinal Chemistry, 2012 , vol. 58, p. 171 - 183

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   56.03
  • LogP   1.7523
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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