Lot numbers can be found on the outside label of a product:
5-Bromo-2-methylquinoline
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CAS No. 54408-52-5
- Cat. No. CS-0103513
- Purity≥98%
- MDL No.MFCD13189490
*For research and further manufacturing use only, not for direct human use.
Structure of 54408-52-5
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General Information
- CAS No. 54408-52-5
- Cat. No. CS-0103513
- Purity ≥98%
- MDL No. MFCD13189490
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₀H₈BrN
- Molecular Weight 222.08
- Synonym(s) 5-Bromoquinaldine
- SMILES CC1=NC2=CC=CC(Br)=C2C=C1
Description
5-Bromo-2-methylquinoline is a heterocyclic scaffold featuring a bromine substituent at the 5-position and a methyl group at the 2-position on the quinoline core. This configuration imparts enhanced electronic modulation and steric profile, enabling efficient integration into transition metal-catalyzed coupling reactions. The molecule exhibits robust stability under standard handling conditions and demonstrates favorable solubility in common organic solvents, facilitating its use in synthetic medicinal chemistry and materials science applications.
Application
5-Bromo-2-methylquinoline serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl architectures. The bromine moiety facilitates palladium-catalyzed coupling with boronic acids, stannanes, and amines, while the methyl group provides moderate electronic stabilization and enhances solubility. Bench-stable and readily purified by column chromatography, it functions reliably in medicinal chemistry and materials synthesis workflows.
Synthesis
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Route1
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591-19-5 -
123-63-7
- ~0%
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In-stock
4965-34-8 -
In-stock
54408-52-5
References
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CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE RENE DESCARTES (PARIS V); DALKO, Peter; PETIT, Morgane; OGDEN, David; BORT, Guillaume; SICARD, Cecile Patent: WO2011/158189 A1, 2011 ; Location in patent: Page/Page column 14-15 ;
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Route2
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91-63-4
- ~29%
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In-stock
54408-52-5
References
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Serafinowska, Halina T.; Blaney, Frank E.; Lovell, Peter J.; Merlo, Giancarlo G.; Scott, Claire M.; Smith, Paul W.; Starr, Kathryn R.; Watson, Jeannette M. Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 20 p. 5581 - 5585
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Route3
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57155-51-8
- ~%
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In-stock
54408-52-5
References
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Kawase; Kikugawa Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 6 p. 1615 - 1623
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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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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Quality Control
Computational Chemistry Data
- TPSA 12.89
- LogP 3.30572
- H_Acceptors 1
- H_Donors 0
- Rotatable_Bonds 0
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Key Words
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