Lot numbers can be found on the outside label of a product:
4-Bromo-6-methoxyquinoline
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CAS No. 42881-66-3
- Cat. No. CS-W014666
- Purity≥95%
- MDL No.MFCD08437074
*For research and further manufacturing use only, not for direct human use.
Structure of 42881-66-3
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General Information
- CAS No. 42881-66-3
- Cat. No. CS-W014666
- Purity ≥95%
- MDL No. MFCD08437074
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₀H₈BrNO
- Molecular Weight 238.08
- Synonym(s) 4-BROMO-6-METHOXYQUINOLIN
- SMILES COC1=CC=C2N=CC=C(Br)C2=C1
Description
4-Bromo-6-methoxyquinoline is a heterocyclic compound featuring a quinoline core with bromine and methoxy substituents at the 4- and 6-positions, respectively. This electron-deficient scaffold enables efficient coupling in palladium-catalyzed cross-coupling reactions. The methoxy group enhances solubility and modulates electronic properties, while the bromine serves as a reliable handle for further functionalization. This molecule exhibits bench-stable handling characteristics and integrates readily into synthetic sequences requiring directed metalation or transition-metal-mediated transformations.
Application
4-Bromo-6-methoxyquinoline serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions due to its well-defined halogen reactivity. The methoxy group enhances solubility and modulates electronic properties, while the quinoline scaffold provides a rigid, planar framework suitable for constructing heterocyclic APIs and functional organic semiconductors. Bench-stable and readily purified by recrystallization, it functions effectively in standard synthetic workflows.
Synthesis
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Route1
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In-stock
23432-39-5 - ~94%
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In-stock
42881-66-3
References
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GLAXO GROUP LIMITED Patent: WO2007/16610 A2, 2007 ; Location in patent: Page/Page column 31 ;
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Route2
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In-stock
13788-72-2 - ~82%
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In-stock
42881-66-3
References
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Raheem, Izzat T.; Goodman, Steven N.; Jacobsen, Eric N. Journal of the American Chemical Society, 2004 , vol. 126, # 3 p. 706 - 707
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Route3
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104-94-9 - ~%
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In-stock
42881-66-3
References
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Tukulula, Matshawandile; Little, Susan; Gut, Jiri; Rosenthal, Philip J.; Wan, Baojie; Franzblau, Scott G.; Chibale, Kelly European Journal of Medicinal Chemistry, 2012 , vol. 57, p. 259 - 267
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS05,GHS07
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Signal Word : Danger
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UN#: 1759
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Class : 8
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Packing Group : Ⅲ
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Hazard Statements : H302-H318
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Precautionary Statements : P264-P270-P280-P305+P351+P338-P330-P501
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Quality Control
Computational Chemistry Data
- TPSA 22.12
- LogP 3.0059
- H_Acceptors 2
- H_Donors 0
- Rotatable_Bonds 1
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Key Words
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