2-Chloro-3-chloromethylquinoline: Properties, Uses & FAQs
2-Chloro-3-chloromethylquinoline: Properties, Uses & FAQs
2-Chloro-3-chloromethylquinoline is a bifunctional halogenated quinoline intermediate widely employed in medicinal and synthetic chemistry for the construction of diverse nitrogen-containing heterocyclic frameworks.
- Chemical Name
- 2-Chloro-3-chloromethylquinoline
- SKU
- C124062
- Molecular Formula
- C10H7Cl2N
- Molecular Weight
- 212.07 g/mol
- Functional Groups
- Ring C-2 chloro (aryl chloride) and C-3 chloromethyl (benzylic chloride)
- Primary Application
- Bifunctional building block for heterocyclic synthesis and medicinal chemistry
- Storage Conditions
- Cool, dry, well-ventilated area; away from moisture and incompatible materials
Overview and Chemical Properties
2-Chloro-3-chloromethylquinoline (SKU C124062) is a halogenated quinoline compound bearing two distinct reactive sites: an aryl chloride at the 2-position of the quinoline ring and a benzylic (chloromethyl) chloride at the 3-position. The molecular formula is C10H7Cl2N with a molecular weight of approximately 212.07 g/mol.
The two chlorine atoms differ substantially in reactivity. The benzylic chloromethyl group at C-3 is considerably more electrophilic and susceptible to nucleophilic substitution under mild conditions, while the aryl chloride at C-2 typically requires more forcing conditions or transition-metal catalysis for substitution. This differential reactivity enables chemoselective functionalization, making the compound a versatile bifunctional scaffold.
The quinoline ring system confers aromatic stability and contributes to π–π stacking interactions relevant in binding to biological targets. The compound is expected to be a solid at room temperature, though researchers should consult the certificate of analysis (CoA) supplied with each lot for confirmed physical data including melting point and purity.
Synthetic Applications
The bifunctional nature of 2-Chloro-3-chloromethylquinoline makes it a valuable building block across several synthetic strategies:
- Nucleophilic substitution at the chloromethyl group: Reactions with amines, thiols, azides, and oxygen nucleophiles at the benzylic position enable straightforward introduction of diverse functional groups, facilitating library synthesis for drug discovery.
- Cross-coupling reactions at C-2: The aryl chloride at the 2-position is amenable to palladium-catalyzed cross-coupling reactions (e.g., Suzuki–Miyaura, Buchwald–Hartwig amination), enabling construction of biaryl and aminoquinoline motifs present in numerous bioactive compounds.
- Cyclization strategies: Sequential or tandem reactions exploiting both halides can afford fused polycyclic heterocyclic systems, expanding access to structurally complex scaffolds.
- Medicinal chemistry: Quinoline-based pharmacophores appear in antimalarial, antibacterial, antiviral, and anticancer agents. 2-Chloro-3-chloromethylquinoline serves as a convenient entry point to substituted quinolines with potential biological activity.
Researchers are encouraged to optimize reaction conditions for their specific nucleophile or coupling partner, as yields and selectivity will depend on the substrate and conditions employed.
Handling, Safety, and Storage
As a halogenated organic compound, 2-Chloro-3-chloromethylquinoline should be handled with appropriate precautions:
- Personal protective equipment (PPE): Wear chemical-resistant gloves, safety goggles, and a lab coat. Work in a well-ventilated fume hood to minimize inhalation exposure.
- Skin and eye contact: Avoid direct contact. In case of skin contact, wash thoroughly with soap and water. For eye contact, rinse immediately with copious water and seek medical attention.
- Storage: Store in a cool, dry, well-ventilated area in a tightly sealed container. Keep away from moisture, strong bases, strong oxidizers, and incompatible nucleophiles that could react with the labile chloromethyl group. Recommended storage temperature is typically 2–8 °C or as specified on the product label and CoA.
- Disposal: Dispose of in accordance with local, regional, and national regulations for halogenated organic waste.
Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use. The SDS contains authoritative hazard classification, first-aid measures, and regulatory information specific to this product lot.
Quality, Purity, and Ordering Information
Aladdin Scientific supplies 2-Chloro-3-chloromethylquinoline under SKU C124062. Each lot is accompanied by a Certificate of Analysis (CoA) confirming identity, purity, and physical characteristics determined by appropriate analytical techniques such as NMR, HPLC, or GC.
Researchers requiring specific purity grades or custom quantities are encouraged to contact Aladdin Scientific's technical sales team for quotation and availability. Bulk quantities may be available subject to manufacturing lead times.
For procurement teams: the product is classified as a research reagent intended for laboratory use only. It is not intended for use in diagnostic procedures, drug formulation, or human/veterinary therapeutic applications without further qualification.
To place an order, visit the Aladdin Scientific website and search by SKU C124062, or contact your regional Aladdin representative. Standard shipping conditions apply; consult the SDS and shipping documentation for any regulatory requirements regarding transport of this material.
Frequently asked questions
What makes 2-Chloro-3-chloromethylquinoline a useful synthetic building block?
The compound contains two chemically distinct halide leaving groups—an aryl chloride at the quinoline 2-position and a reactive benzylic chloride at the 3-position—that can be functionalized selectively or sequentially. This allows medicinal and synthetic chemists to introduce different functional groups at each site, enabling efficient construction of diverse quinoline-based libraries. The quinoline core itself is a privileged scaffold found in many bioactive molecules, adding further strategic value.
How should I store 2-Chloro-3-chloromethylquinoline to maintain its stability?
Store the compound in a tightly sealed container in a cool, dry, and well-ventilated location, away from moisture, strong bases, and oxidizing agents. The reactive benzylic chloromethyl group is susceptible to hydrolysis and reaction with adventitious nucleophiles, so moisture exclusion is particularly important. Refer to the product label and CoA for the recommended storage temperature specific to your lot.
Can the two chloride groups in 2-Chloro-3-chloromethylquinoline be functionalized independently?
Yes, the differential reactivity of the two chlorides allows chemoselective manipulation. The benzylic chloromethyl group at C-3 reacts readily with soft or hard nucleophiles (amines, thiols, alkoxides) under mild conditions, while the aryl chloride at C-2 typically requires transition-metal catalysis (e.g., Pd-catalyzed coupling) or harsher nucleophilic aromatic substitution conditions. By choosing appropriate reagents and conditions, chemists can functionalize each position independently in a controlled sequence.
Is 2-Chloro-3-chloromethylquinoline suitable for Suzuki–Miyaura cross-coupling reactions?
The aryl chloride at the 2-position of the quinoline ring is in principle amenable to palladium-catalyzed Suzuki–Miyaura coupling with arylboronic acids or esters, as quinoline-2-chloro bonds are activated by the electron-withdrawing nitrogen of the ring. Researchers should optimize catalyst loading, ligand choice, base, and solvent to achieve good yields. Care should be taken to protect or react the chloromethyl group prior to or independently of the coupling step if selectivity is required.
What analytical methods are used to confirm the identity and purity of C124062?
Aladdin Scientific confirms the identity and purity of each lot of 2-Chloro-3-chloromethylquinoline using standard analytical techniques such as proton NMR spectroscopy for structural confirmation, and HPLC or GC for purity determination. The Certificate of Analysis (CoA) accompanying each shipment reports these results. Customers may request a CoA for their specific lot number through the Aladdin Scientific website or customer service team.
References
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for nucleophilic substitution and cross-coupling reactions.)
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Textbook-level reference for halide reactivity and aromatic chemistry.)
- Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95 (7), 2457–2483. doi:10.1021/cr00039a007
- Aladdin Scientific Certificate of Analysis, SKU C124062, 2-Chloro-3-chloromethylquinoline. (Consult current lot CoA for confirmed physical and analytical data.)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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