4-Chloro-6-iodo-1-methylquinolin-2(1H)-one | CAS 2375193-30-7 | 98% | Off-white to Light Yellow Solid | Pharmaceutical Intermediate & Organic Synthesi

1. Product Overview

4-Chloro-6-iodo-1-methylquinolin-2(1H)-one (CAS: 2375193-30-7) is a halogenated N-methylated quinolin-2-one derivative with the molecular formula C₁₀H₇ClINO and a molecular weight of 319.53 g/mol. This compound features a quinoline core bearing a chlorine atom at the 4-position, an iodine atom at the 6-position, and a methyl group on the lactam nitrogen (N1). The structural motif is a close analogue of 4-chloro-6-iodo-2(1H)-quinolinone, with the N-methylation enhancing lipophilicity and modifying the hydrogen-bonding profile, which is advantageous in medicinal chemistry optimization.

The presence of orthogonal halogen substituents (Cl and I) provides distinct and sequentially addressable reactivity: the iodine at C6 is highly active in palladium-catalyzed cross-coupling reactions (Suzuki, Sonogashira, Heck, etc.), while the chlorine at C4 can undergo selective nucleophilic aromatic substitution. This makes the compound a valuable and versatile building block for constructing complex quinoline-based scaffolds in drug discovery and fine chemical synthesis.

2. Key Features and Advantages

• Dual Halogen Reactivity with N-Methylation: The Cl/I combination plus N-methyl group offers orthogonal functionalization routes and improved lipophilicity for better membrane permeability in bioactive molecule design.

• High Regioselectivity Potential: Iodine at C6 enables facile Pd-catalyzed couplings; chlorine at C4 remains available for subsequent nucleophilic displacement, supporting stepwise library synthesis.

• High Purity Grade: Typically supplied at ≥98% purity (HPLC), suitable for sensitive pharmaceutical R&D and SAR studies.

• Well-Defined Heterocyclic Core: The 1-methylquinolin-2(1H)-one framework is a privileged structure in kinase inhibitor and antiparasitic agent development.

• Stable Solid Form: Off-white to light yellow solid with good stability under recommended cold storage, minimizing decomposition during handling.

• Scalable Availability: Offered from 1 g up to kilogram scale to support early-stage screening through process development.

3. Main Applications

3.1 Pharmaceutical Intermediate & Drug Discovery

This compound is primarily used as a key intermediate in medicinal chemistry for the synthesis of quinolinone-based drug candidates. The core is widely explored in:

• Kinase inhibitors targeting VEGFR, KDR, EGFR, and related pathways for anticancer therapy.

• Antiparasitic agents against trypanosomiasis, leishmaniasis, and malaria.

• Anti-inflammatory and antimicrobial small molecules leveraging the quinolinone pharmacophore.

3.2 Organic Synthesis & Diversification

The iodine substituent serves as an ideal handle for Pd-catalyzed cross-couplings to introduce aryl, alkynyl, vinyl, or amine groups at C6, while the C4-chlorine can later be substituted by amines, alkoxides, or thiols. This sequential functionalization is extensively used in:

• Design of focused compound libraries for high-throughput screening.

• Synthesis of fluorescent probes and bioorthogonal labeling reagents derived from quinolinones.

• Construction of fused heterocyclic systems via intramolecular cyclizations after cross-coupling.

3.3 Process Chemistry & Scale-Up

The robust reactivity profile and commercial availability make it suitable for route scouting and pilot-scale synthesis of active pharmaceutical ingredients (APIs) where the 1-methylquinolin-2-one core is a final or penultimate intermediate.

4. Technical Specifications

5. Storage and Handling

Storage Conditions

• Store in a cool, dry place at 2–8 °C.

• Keep container tightly closed and protected from light (amber vial or aluminum-foil wrapped).

• Store away from strong oxidizers, strong bases, and sources of ignition.

• For long-term storage, keep under inert atmosphere (argon or nitrogen) to prevent slow oxidative changes.

Handling Precautions

• Handle in a well-ventilated area or fume hood to avoid inhalation of dust.

• Avoid contact with skin, eyes, and clothing.

• Use appropriate personal protective equipment as outlined in Section 6.

6. Safety Overview

Hazard Identification

• Not classified as a GHS hazardous substance based on available data, but intended strictly for industrial and research use.

• May cause mild irritation to eyes, skin, and respiratory tract upon contact or dust inhalation.

• Not for human or veterinary therapeutic use, not for food or cosmetic application.

First Aid Measures

• Inhalation: Move to fresh air. Seek medical attention if breathing difficulty or persistent irritation occurs.

• Skin Contact: Remove contaminated clothing. Rinse skin thoroughly with soap and water.

• Eye Contact: Rinse immediately with plenty of running water for at least 15 minutes. Consult an ophthalmologist if irritation persists.

• Ingestion: Rinse mouth. Do NOT induce vomiting. Seek immediate medical attention.

Personal Protective Equipment (PPE)

• Eye/Face Protection: Safety goggles or face shield.

• Hand Protection: Nitrile chemical-resistant gloves.

• Body Protection: Lab coat, long sleeves, closed-toe shoes.

• Respiratory Protection: NIOSH-approved dust mask or particulate respirator if handling generates airborne particles.

Disposal Considerations

• Dispose of as hazardous chemical waste in accordance with local, regional, and national regulations.

• Do not dispose of in drains or release into the environment.

• Incinerate in a licensed chemical waste facility.

Disclaimer: This product is intended for industrial use and scientific research only. It is not for human or animal consumption, diagnostic, or therapeutic use. Users must ensure compliance with all applicable laws and regulations.