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CS-W001157 4
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2-Amino-5-bromo-4-methyl-3-nitropyridine

  • CAS No. 100367-40-6

  • Cat. No. CS-M1656
  • Purity≥96%
  • MDL No.MFCD00092197

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

2-Amino-5-bromo-4-methyl-3-nitropyridine|CS-M1656

Structure of 100367-40-6

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General Information

  • CAS No. 100367-40-6
  • Cat. No. CS-M1656
  • Purity ≥96%
  • MDL No. MFCD00092197
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆BrN₃O₂
  • Molecular Weight 232.03
  • Synonym(s) 5-bromo-4-methyl-3-nitropyridin-2-amine
  • SMILES CC1=C([N+]([O-])=O)C(N)=NC=C1Br

Description

2-Amino-5-bromo-4-methyl-3-nitropyridine features a fused pyridine core bearing strategically positioned amino, bromo, methyl, and nitro substituents. This electron-deficient heterocycle enables direct functionalization in cross-coupling and cyclization reactions. The ortho-nitro group enhances reactivity toward nucleophilic substitution, while the amino handle supports derivatization. Bench-stable under standard conditions, it serves as a key intermediate for bioactive molecule synthesis.

Application

2-Amino-5-bromo-4-methyl-3-nitropyridine serves as a versatile building block for heterocyclic synthesis, enabling efficient access to substituted pyridine scaffolds via cross-coupling and reduction strategies. Its complementary functional groups—bromine for Pd-catalyzed coupling, nitro for selective reduction, and amino/methyl groups for derivatization—offer high synthetic flexibility. Bench-stable and compatible with standard purification methods, it facilitates rapid prototyping in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Liu, Wansheng; Patel, Sunil S.; Cuniere, Nicolas; Lear, Yvonne; Deshpande, Prashant P.; Simon, Jeffrey N.; Lai, Chiajen; Pullockaran, Annie J.; Soundararajan, Nachimuthu; Bien, Jeffrey T. Patent: US2007/32503 A1, 2007 ; Location in patent: Page/Page column 8-9; 10 ;
  • Route2

    References

    • Journal of the American Chemical Society, , vol. 79, p. 6421,6423,6424
  • Route3

    References

    • Journal of the American Chemical Society, , vol. 79, p. 6421,6423,6424

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   82.05
  • LogP   1.64292
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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