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CS-W001157 4
Total: USD 88.00

8-Amino-6-methoxyquinoline

  • CAS No. 90-52-8

  • Cat. No. CS-W022555
  • Purity≥96%
  • MDL No.MFCD00672902

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

8-Amino-6-methoxyquinoline|CS-W022555

Structure of 90-52-8

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General Information

  • CAS No. 90-52-8
  • Cat. No. CS-W022555
  • Purity ≥96%
  • MDL No. MFCD00672902
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₀N₂O
  • Molecular Weight 174.20
  • Synonym(s) 6-Methoxyquinolin-8-ylamine
  • SMILES COC1=CC(N)=C2N=CC=CC2=C1

Description

8-Amino-6-methoxyquinoline delivers a strategically positioned amino group and methoxy substituent on the quinoline scaffold, enabling facile functionalization in synthetic transformations. This electron-rich framework supports conjugation in fluorescent probes and serves as a key intermediate in medicinal chemistry applications requiring polar, aromatic heterocycles with enhanced solubility and stability under standard conditions.

Application

8-Amino-6-methoxyquinoline serves as a versatile building block in medicinal chemistry, enabling direct incorporation into heterocyclic scaffolds via palladium-catalyzed cross-coupling and electrophilic substitution reactions. The amino group facilitates derivatization, while the methoxy substituent enhances solubility and modulates electronic properties. Its bench-stable crystalline form simplifies handling and purification, making it well-suited for multi-step synthesis campaigns targeting kinase inhibitors and antimalarial agents.

Synthesis

  • Route1

    References

    • Armer, Richard E.; Barlow, Jacqueline S.; Chopra, Narinder; Dutton, Christopher J.; Greenway, David H.J.; Greenwood, Sean D.W.; Lad, Nita; Shaw, Jonothan; Thompson, Adrian P.; Thong, Kam-Wah; Tommasini, Ivan Bioorganic and Medicinal Chemistry Letters, 1999 , vol. 9, # 16 p. 2425 - 2430
  • Route2
    • In-stock
      6-Methoxy-8-nitroquinoline|CS-0043044
      85-81-4
    • ~0%
    • In-stock
      8-Amino-6-methoxyquinoline|CS-W022555
      90-52-8
    • null|null
      57742-99-1

    References

    • Allahyari; Strother; Fraser; Verbiscar Journal of Medicinal Chemistry, 1984 , vol. 27, # 3 p. 407 - 410
  • Route3
    • null|null
      57743-00-7
    • ~29%
    • In-stock
      8-Amino-6-methoxyquinoline|CS-W022555
      90-52-8
    • null|null
      81852-49-5

    References

    • Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , p. 671 - 672

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   48.14
  • LogP   1.8256
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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