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CS-W001157 4
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2-Methylquinolin-8-amine

  • CAS No. 18978-78-4

  • Cat. No. CS-W002143
  • Purity≥98%
  • MDL No.MFCD00023998

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

2-Methylquinolin-8-amine|CS-W002143

Structure of 18978-78-4

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General Information

  • CAS No. 18978-78-4
  • Cat. No. CS-W002143
  • Purity ≥98%
  • MDL No. MFCD00023998
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₀N₂
  • Molecular Weight 158.20
  • Synonym(s) 8-Aminoquinaldine
  • SMILES Cc1ccc2c(n1)c(N)ccc2

Description

2-Methylquinolin-8-amine features a sterically accessible quinoline scaffold with a strategically positioned amino group at the 8-position, enabling direct incorporation into transition metal-catalyzed coupling reactions. The methyl substitution enhances electronic modulation and improves solubility in common organic solvents, facilitating use in synthetic workflows requiring stable, bench-ready heterocyclic building blocks.

Application

2-Methylquinolin-8-amine serves as a versatile building block in medicinal chemistry, enabling direct access to quinoline-based scaffolds prevalent in kinase inhibitors and antimalarial agents. Its ortho-amino functionality facilitates electrophilic substitution, metal-catalyzed coupling, and cyclization reactions under standard conditions. The methyl group enhances metabolic stability and modulates electronic properties, while the amine provides a handle for derivatization via acylation, alkylation, or reductive amination. Bench-stable and readily purified by recrystallization, it functions reliably in multi-step synthesis and scale-up workflows.

Synthesis

  • Route1

    References

    • VIFOR (INTERNATIONAL) AG Patent: US2012/214803 A1, 2012 ; Location in patent: Page/Page column 126 ; US 20120214803 A1
  • Route2
    • In-stock
      N-Boc-1,2-phenylenediamine|CS-M2229
      146651-75-4
    • null|null
      109-92-2
    • ~50%
    • In-stock
      2-Methylquinolin-8-amine|CS-W002143
      18978-78-4

    References

    • De, Kavita; Legros, Julien; Crousse, Benoit; Chandrasekaran, Srinivasan; Bonnet-Delpon, Daniele Organic and Biomolecular Chemistry, 2011 , vol. 9, # 2 p. 347 - 350
  • Route3

    References

    • Belser, Peter; Bernhard, Stefan; Guerig, Urs Tetrahedron, 1996 , vol. 52, # 8 p. 2937 - 2944

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H318
Precautionary Statements : P264-P270-P280-P330-P501

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Computational Chemistry Data

  • TPSA   38.91
  • LogP   2.12542
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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