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CS-W001157 4
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5-Bromoquinolin-2-amine

  • CAS No. 347146-12-7

  • Cat. No. CS-0214756
  • Purity≥97%
  • MDL No.None

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

5-Bromoquinolin-2-amine|CS-0214756

Structure of 347146-12-7

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General Information

  • CAS No. 347146-12-7
  • Cat. No. CS-0214756
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇BrN₂
  • Molecular Weight 223.07
  • Synonym(s) 5-Bromo-quinolin-2-ylamine
  • SMILES NC1=NC2=CC=CC(Br)=C2C=C1

Description

5-Bromoquinolin-2-amine features a bromine atom at the 5-position and an amino group at the 2-position of the quinoline scaffold, enabling selective coupling reactions. This electron-deficient heterocycle integrates readily into pharmaceutical intermediates and functional materials, offering enhanced reactivity in palladium-catalyzed transformations under standard conditions.

Application

5-Bromoquinolin-2-amine serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions for the construction of biaryl scaffolds. Its bromine substituent facilitates efficient C–C bond formation under standard Suzuki, Stille, or Negishi conditions, while the pendant amine supports derivatization and coordination in catalytic systems. The molecule exhibits good bench stability and is compatible with diverse functional groups, making it a practical choice for the synthesis of quinoline-based pharmaceutical candidates and ligands.

Synthesis

  • Route1

    References

    • Cheng, Yuan; Judd, Ted C.; Bartberger, Michael D.; Brown, James; Chen, Kui; Fremeau Jr., Robert T.; Hickman, Dean; Hitchcock, Stephen A.; Jordan, Brad; Li, Vivian; Lopez, Patricia; Louie, Steven W.; Luo, Yi; Michelsen, Klaus; Nixey, Thomas; Powers, Timothy S.; Rattan, Claire; Sickmier, E. Allen; St. Jean Jr., David J.; Wahl, Robert C.; Wen, Paul H.; Wood, Stephen Journal of Medicinal Chemistry, 2011 , vol. 54, # 16 p. 5836 - 5857
  • Route2

    References

    • Cheng, Yuan; Judd, Ted C.; Bartberger, Michael D.; Brown, James; Chen, Kui; Fremeau Jr., Robert T.; Hickman, Dean; Hitchcock, Stephen A.; Jordan, Brad; Li, Vivian; Lopez, Patricia; Louie, Steven W.; Luo, Yi; Michelsen, Klaus; Nixey, Thomas; Powers, Timothy S.; Rattan, Claire; Sickmier, E. Allen; St. Jean Jr., David J.; Wahl, Robert C.; Wen, Paul H.; Wood, Stephen Journal of Medicinal Chemistry, 2011 , vol. 54, # 16 p. 5836 - 5857

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-P330-P362+P364-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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