1. Product Overview
Methyl 2-(quinolin-3-yl)acetate (CAS No. 847458-93-9) is a quinoline-derived methyl ester with the acetate moiety attached at the C3 position of the quinoline ring. Supplied at minimum 95% purity (HPLC), this white to off-white crystalline solid (molecular formula C₁₂H₁₁NO₂, MW 201.22) is a versatile heteroaromatic building block in medicinal chemistry and pharmaceutical intermediate synthesis. The quinoline scaffold is a privileged structure found in numerous FDA-approved drugs (e.g., chloroquine, quinine analogues, kinase inhibitors), while the methyl ester at the 3-position side chain provides a readily hydrolyzable handle for conversion to the corresponding carboxylic acid, amide formation, reduction to the alcohol, or nucleophilic substitution after activation. This compound is widely used in SAR studies, library construction of quinoline-based bioactive molecules, and as a key synthon in multi-step API routes targeting antimalarial, anticancer, and antimicrobial indications.
2. Key Features and Advantages
• High Purity & Batch Consistency — Minimum 95% purity verified by HPLC and ¹H NMR, ensuring clean downstream transformations (hydrolysis, amidation, reduction) with minimal ester-related impurities.
• Privileged Quinoline Scaffold — The quinoline core is a well-established pharmacophore in antimalarial, anticancer, antiviral, and CNS-active agents; C3-substitution enables precise modulation of electronic and steric properties.
• Versatile Ester Functionality — Methyl ester is stable under neutral/basic conditions but readily hydrolyzed to acid, reduced to alcohol (LiAlH₄/NaBH₄ → 3-(2-hydroxyethyl)quinoline), or converted to amides/esters with diverse amines/alcohols, supporting orthogonal derivatization.
• C3-Position Reactivity — Unlike C2-quinoline esters, the C3-linked acetate avoids competing quinoline N-alkylation issues and offers cleaner α-carbon functionalization (e.g., aldol, alkylation after deprotonation with LDA).
• Stable Crystalline Solid — Good shelf stability as a dry solid under recommended cool, dry storage; compatible with common organic solvents (DMSO, DMF, MeOH, CH₂Cl₂, THF, EtOAc).
3. Main Applications
• Medicinal Chemistry & Drug Discovery — Used as a core intermediate for synthesizing quinoline-based antimalarial agents (chloroquine/primaquine analogues), kinase inhibitors, antimicrobials, anti-inflammatory compounds, and fluorescent probes; ideal for SAR exploration via ester hydrolysis → amidation or alcohol reduction → further functionalization.
• Pharmaceutical Intermediate — Serves as a key synthon in multi-step API synthesis where the quinoline C3-side chain is elaborated: e.g., hydrolyze to acid for peptide coupling, reduce to alcohol for oxidation or substitution, or perform α-alkylation for branched side chains.
• Heterocyclic Library Construction — Employed in academic and CRO/CMO settings to generate focused quinoline libraries: hydrolyze to carboxylic acid → couple with amine arrays (amides), reduce to alcohol → convert to halides/azides, or use the α-methylene for Knoevenagel/Michael additions.
• Material & Probe Chemistry — Quinoline is weakly fluorescent; this ester can be converted to quinoline-based fluorophores or ligands for metal coordination (N of quinoline) in catalysis and sensing applications.
4. Technical Specifications
5. Storage and Handling
• Storage Temperature — Store at 2–8°C in a cool, dry place. For long-term storage (>12 months), keep in a tightly sealed container under an inert atmosphere (argon or nitrogen) to prevent slow hydrolysis of the methyl ester by ambient moisture and to avoid oxidation of the quinoline ring.
• Packaging Options | Available in 100 mg, 250 mg, 500 mg, 1 g, 5 g, and bulk quantities upon request.
• Handling Precautions — Use standard laboratory PPE (safety glasses, nitrile gloves, lab coat). Avoid dust generation; handle in a well-ventilated area or fume hood. The ester is relatively stable but can hydrolyze under strongly acidic/basic conditions—avoid prolonged exposure to moist air during weighing.
• Shelf Life — When stored as recommended (sealed, 2–8°C, dry, inert atmosphere), the product maintains ≥95% purity for at least 24 months from the date of manufacture. Allow sealed container to reach room temperature before opening to prevent moisture condensation on the solid.
6. Safety Overview
• Hazard Classification (GHS) — GHS07 signal word “Warning”; typical quinoline esters may carry H315 (causes skin irritation), H319 (causes eye irritation), H335 (may cause respiratory irritation). Not classified as acutely toxic or carcinogenic under standard criteria; intended strictly for research and industrial synthesis, not for human/veterinary therapeutic use or as a food additive.
• First Aid Measures — Skin contact: wash thoroughly with soap and water. Eye contact: rinse immediately with plenty of water for ≥15 min, lifting eyelids; seek medical attention if irritation persists. Inhalation: move to fresh air; if breathing difficulty occurs, administer oxygen and consult a physician. Ingestion: rinse mouth, do NOT induce vomiting; seek medical advice.
• Firefighting Measures — Combustible solid. Use water spray, dry chemical, carbon dioxide, or alcohol-resistant foam. Wear self-contained breathing apparatus and full protective gear if involved in fire.
• Disposal Considerations — Dispose as nitrogen-containing heterocyclic organic ester waste in accordance with local, regional, and national regulations. Do not discharge to drains, waterways, or soil. Contaminated packaging should be emptied and sent for licensed chemical-waste disposal.
