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CS-W001157 4
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7-Bromo-5-methoxyquinoline

  • CAS No. 1378860-76-4

  • Cat. No. CS-B0550
  • Molecule weight238.08
  • Purity≥98%
  • MDL No.MFCD11878498

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

7-Bromo-5-methoxyquinoline|CS-B0550

Structure of 1378860-76-4

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General Information

  • CAS No. 1378860-76-4
  • Cat. No. CS-B0550
  • Purity ≥98%
  • MDL No. MFCD11878498
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈BrNO
  • Molecular Weight 238.08
  • Synonym(s) 7-bromo-5-methoxy-quinoline
  • SMILES BrC1=CC(OC)=C2C(N=CC=C2)=C1

Description

7-Bromo-5-methoxyquinoline is a halogenated quinoline derivative featuring a bromine atom at the 7-position and a methoxy group at the 5-position. This substitution pattern imparts enhanced electron-withdrawing character and improved solubility in organic solvents, facilitating its use in transition metal-catalyzed cross-coupling reactions. The molecule exhibits bench-stable handling under standard conditions and serves as a valuable scaffold for medicinal chemistry and materials science applications.

Application

7-Bromo-5-methoxyquinoline serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions for the construction of biaryl scaffolds. The bromine at C7 provides a reliable site for Suzuki, Stille, or Negishi coupling, while the methoxy group at C5 offers moderate electron donation and orthogonality to common protecting groups. Its bench-stable crystalline form facilitates handling and purification, making it well-suited for iterative synthesis in API development workflows.

Synthesis

  • Route1

    References

    • BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KLICIC, Jasna; SCHAENZLE, Gerhard; WOLLIN, Stefan Ludwig Michael; CONVERS-REIGNIER, Serge Gaston; EAST, Stephen Peter; MARLIN, Frederic Jacques; MCCARTHY, Clive; SCOTT, John Patent: WO2013/14060 A1, 2013 ; Location in patent: Page/Page column 49 ; WO 2013/014060 A1

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   22.12
  • LogP   3.0059
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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