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CS-W001157 4
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2-Amino-3-methoxypyridine

  • CAS No. 10201-71-5

  • Cat. No. CS-W019632
  • Purity≥97%
  • MDL No.MFCD07374874

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

2-Amino-3-methoxypyridine|CS-W019632

Structure of 10201-71-5

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General Information

  • CAS No. 10201-71-5
  • Cat. No. CS-W019632
  • Purity ≥97%
  • MDL No. MFCD07374874
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₈N₂O
  • Molecular Weight 124.14
  • Synonym(s) 3-Methoxypyridin-2-amine
  • SMILES COC1=CC=CN=C1N

Description

2-Amino-3-methoxypyridine is a bench-stable heterocyclic building block featuring an electron-rich pyridine core with strategically positioned amino and methoxy groups. This combination enables direct functionalization in transition-metal-catalyzed couplings and facilitates integration into bioactive scaffolds. The para-oriented substituents enhance solubility and reduce aggregation during synthesis.

Application

2-Amino-3-methoxypyridine serves as a versatile building block in medicinal chemistry, enabling the construction of pyridine-based scaffolds through palladium-catalyzed cross-coupling and electrophilic substitution reactions. Its amino and methoxy groups offer orthogonal reactivity for sequential functionalization, while its bench stability facilitates handling and purification in multi-step syntheses.

Synthesis

  • Route1

    References

    • Huang, Zilin; Jin, Jeff; Machajewski, Timothy; Antonios-McCrea, William R.; McKenna, Maureen; Poon, Daniel; Renhowe, Paul A.; Sendzik, Martin; Shafer, Cynthia; Smith, Aaron; Xu, Yongjin; Zhang, Qiong; Chen, Zheng Patent: US2013/210818 A1, 2013 ; Location in patent: Paragraph 0380 ;
  • Route2

    References

    • Fantasia, Serena; Windisch, Johannes; Scalone, Michelangelo Advanced Synthesis and Catalysis, 2013 , vol. 355, # 4 p. 627 - 631
  • Route3
    • null|null
      186581-53-3
    • In-stock
      2-Amino-3-hydroxypyridine|CS-W007794
      16867-03-1
    • ~46%
    • In-stock
      2-Amino-3-methoxypyridine|CS-W019632
      10201-71-5

    References

    • Trapani, Giuseppe; Franco, Massimo; Latrofa, Andrea; Ricciardi, Laura; Carotti, Angelo; Serra, Mariangela; Sanna, Enrico; Biggio, Giovanni; Liso, Gaetano Journal of Medicinal Chemistry, 1999 , vol. 42, # 19 p. 3934 - 3941

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   48.14
  • LogP   0.6724
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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