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CS-W001157 4
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2-Bromoquinolin-4-amine

  • CAS No. 36825-35-1

  • Cat. No. CS-W006506
  • Molecule weight223.07
  • Purity≥97%
  • MDL No.MFCD08705640

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

2-Bromoquinolin-4-amine|CS-W006506

Structure of 36825-35-1

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General Information

  • CAS No. 36825-35-1
  • Cat. No. CS-W006506
  • Purity ≥97%
  • MDL No. MFCD08705640
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇BrN₂
  • Molecular Weight 223.07
  • Synonym(s) 4-AMINO-2-BROMOQUINOLINE
  • SMILES BrC1=NC2=CC=CC=C2C(N)=C1

Description

2-Bromoquinolin-4-amine features a bromine atom at the 2-position and a primary amine at the 4-position of the quinoline core, enabling direct functionalization in cross-coupling reactions. The electron-deficient aromatic system enhances reactivity in palladium-catalyzed transformations, while the amine group offers convenient derivatization pathways for pharmaceutical and materials applications.

Application

2-Bromoquinolin-4-amine serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions for the construction of biaryl scaffolds. Its bromine and amine functionalities offer orthogonal reactivity, facilitating sequential functionalization in late-stage diversification. The compound exhibits good bench stability and is compatible with standard purification protocols, making it well-suited for modular synthesis workflows.

Synthesis

  • Route1
    • 2-Bromo-4-nitroquinoline|CS-1698321
      20146-63-8
    • ~43%
    • In-stock
      2-Bromoquinolin-4-amine|CS-W006506
      36825-35-1

    References

    • UNIVERSITEIT LEIDEN; CAN-FITE BIOPHARMA LTD.; IJZERMAN, Adriaan; GOBLYOS, Aniko; BRUSSEE, Johannes Patent: WO2010/20981 A1, 2010 ; Location in patent: Page/Page column 29; 1/2 ;
  • Route2

    References

    • Boudet, Nadege; Lachs, Jennifer R.; Knochel, Paul Organic Letters, 2007 , vol. 9, # 26 p. 5525 - 5528
  • Route3

    References

    • Verheij, Mark H. P.; Thompson, Andrew J.; Van Muijlwijk-Koezen, Jacqueline E.; Lummis, Sarah C. R.; Leurs, Rob; De Esch, Iwan J. P. Journal of Medicinal Chemistry, 2012 , vol. 55, # 20 p. 8603 - 8614

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   38.91
  • LogP   2.5795
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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