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CS-W001157 4
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2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile

  • CAS No. 675126-27-9

  • Cat. No. CS-0022482
  • Purity≥97%
  • MDL No.MFCD11110477

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

2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile|CS-0022482

Structure of 675126-27-9

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General Information

  • CAS No. 675126-27-9
  • Cat. No. CS-0022482
  • Purity ≥97%
  • MDL No. MFCD11110477
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₁N₃O₃
  • Molecular Weight 291.35
  • Synonym(s) Benzonitrile, 2-amino-4-methoxy-5-[3-(4-morpholinyl)propoxy]-
  • SMILES N#CC1=CC(OCCCN2CCOCC2)=C(OC)C=C1N

Description

This boronate moiety integrates a methoxy-substituted aromatic core with a morpholinopropoxy side chain, delivering enhanced solubility and metabolic stability. The para-nitro group enables efficient coupling in Suzuki-Miyaura reactions, while the amino functionality offers direct derivatization potential for probe development.

Application

2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile serves as a versatile building block for heterocyclic synthesis, enabling efficient access to substituted benzimidazoles and quinoline scaffolds. The ortho-amino and nitrile groups facilitate cyclization under mild conditions, while the methoxy and morpholinopropoxy substituents provide solubility and modulate electronic properties. Bench-stable and compatible with standard purification protocols, it functions effectively in multi-step medicinal chemistry campaigns requiring functional group tolerance and predictable reactivity.

Synthesis

  • Route1

    References

    • ASTRAZENECA AB; ASTRAZENECA UK LIMITED Patent: WO2004/24703 A1, 2004 ; Location in patent: Page 10 ; WO 2004/024703 A1
  • Route2
    • 4-(3-Chloropropyl)morpholine Pramoxine Impurity|CS-0229750
      7357-67-7
    • ~%
    • In-stock
      2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile|CS-0022482
      675126-27-9

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 16, # 15 p. 4102 - 4106
  • Route3
    • 4-Methoxy-3-(3-morpholinopropoxy)benzonitrile|CS-0574575
      675126-28-0
    • ~%
    • In-stock
      2-Amino-4-methoxy-5-(3-morpholinopropoxy)benzonitrile|CS-0022482
      675126-27-9

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 16, # 15 p. 4102 - 4106

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   80.74
  • LogP   1.25018
  • H_Acceptors   6
  • H_Donors   1
  • Rotatable_Bonds   6

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