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

  • CAS No. 27582-14-5

  • Cat. No. CS-W006814
  • Purity≥95%
  • MDL No.MFCD08277309

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

4-Amino-2-methyl-3-nitropyridine|CS-W006814

Structure of 27582-14-5

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General Information

  • CAS No. 27582-14-5
  • Cat. No. CS-W006814
  • Purity ≥95%
  • MDL No. MFCD08277309
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₇N₃O₂
  • Molecular Weight 153.14
  • Synonym(s) 4-Pyridinamine, 2-methyl-3-nitro-
  • SMILES CC1=C([N+]([O-])=O)C(C=CN1)=N

Description

4-Amino-2-methyl-3-nitropyridine features a pyridine core functionalized with electron-donating amino and methyl groups at positions 4 and 2, respectively, paired with a strongly electron-withdrawing nitro group at position 3. This arrangement creates a polar, resonance-stabilized system ideal for nucleophilic substitution and transition-metal-catalyzed coupling reactions. The compound exhibits bench-stable handling under standard conditions and integrates readily into complex heterocyclic scaffolds.

Application

4-Amino-2-methyl-3-nitropyridine serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted pyridine scaffolds through sequential functionalization. The amino and nitro groups exhibit orthogonal reactivity, facilitating selective transformations such as reduction, coupling, or electrophilic substitution. Its bench-stable nature and compatibility with common reaction conditions make it suitable for iterative synthesis workflows in medicinal chemistry and API development.

Synthesis

  • Route1

    References

    • Tite, Tony; Lougiakis, Nikolaos; Marakos, Panagiotis; Pouli, Nicole Synlett, 2009 , # 18 p. 2927 - 2930

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   82.78
  • LogP   0.71079
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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