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CS-W001157 4
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5-Bromo-2-methyl-3-nitropyridine

  • CAS No. 911434-05-4

  • Cat. No. CS-W014827
  • Purity≥97%
  • MDL No.MFCD09031419

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

5-Bromo-2-methyl-3-nitropyridine|CS-W014827

Structure of 911434-05-4

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General Information

  • CAS No. 911434-05-4
  • Cat. No. CS-W014827
  • Purity ≥97%
  • MDL No. MFCD09031419
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrN₂O₂
  • Molecular Weight 217.02
  • Synonym(s) pyridine, 5-bromo-2-methyl-3-nitro-
  • SMILES O=[N+](C1=CC(Br)=CN=C1C)[O-]

Description

5-Bromo-2-methyl-3-nitropyridine features a trifunctional pyridine core with bromine, methyl, and nitro groups positioned for selective cross-coupling and electrophilic substitution. The electron-deficient ring enhances reactivity in palladium-catalyzed transformations, while the methyl group provides steric control. This compound serves as a key intermediate in medicinal chemistry and agrochemical synthesis.

Application

5-Bromo-2-methyl-3-nitropyridine serves as a versatile building block for C–H functionalization and cross-coupling reactions, enabling efficient access to substituted pyridine scaffolds. Its bromo group facilitates palladium-catalyzed coupling, while the nitro function supports sequential reduction and derivatization. The methyl substituent enhances regiochemical control in electrophilic substitution. This compound exhibits bench stability and compatibility with standard purification methods, making it suitable for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • Diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate|CS-0541094
      911434-04-3
    • ~98%
    • In-stock
      5-Bromo-2-methyl-3-nitropyridine|CS-W014827
      911434-05-4

    References

    • ASTRAZENECA AB Patent: US2008/194552 A1, 2008 ; Location in patent: Page/Page column 40 ; US 20080194552 A1
  • Route2
    • In-stock
      5-Bromo-2-chloro-3-nitropyridine|CS-D0810
      67443-38-3
    • null|null
      105-53-3
    • ~62%
    • In-stock
      5-Bromo-2-methyl-3-nitropyridine|CS-W014827
      911434-05-4

    References

    • SMITHKLINE BEECHAM CORPORATION Patent: WO2008/157191 A2, 2008 ; Location in patent: Page/Page column 83-84 ; WO 2008/157191 A2
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 54, # 6 p. 1789 - 1811

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   56.03
  • LogP   2.06072
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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