2-Chlorobenzoxazole

2-Chlorobenzoxazole is a versatile heterocyclic intermediate that serves as a key building block for the synthesis of diverse pharmaceutical compounds, agrochemicals, and functional materials. The benzoxazole core of 2-Chlorobenzoxazole is a privileged scaffold in medicinal chemistry, appearing in numerous bioactive molecules with antibacterial, antifungal, anticancer, and CNS activities. As an electrophilic heteroaryl chloride, 2-Chlorobenzoxazole readily undergoes nucleophilic aromatic substitution reactions, enabling the introduction of amines, alkoxides, and other nucleophiles at the 2-position to generate functionalized benzoxazole derivatives. 2-Chlorobenzoxazole also participates in cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings, expanding its utility in complex molecule synthesis. In addition, 2-Chlorobenzoxazole serves as a precursor to 2-substituted benzoxazoles, which are valuable for applications ranging from fluorescent probes to organic electronics. The air sensitivity of 2-Chlorobenzoxazole necessitates storage under inert gas and protection from moisture to maintain its quality and reactivity .

Product Parameters

Synthetic Route

General procedure for the synthesis of 2-chlorobenzoxazole using 2-mercaptobenzoxazole as the raw material: Suspend 2-mercaptobenzoxazole (10 mmol, 1.51 g) in SOCl₂ (50 mL), and add a few drops of DMF as a catalyst. Heat the reaction mixture under reflux for 5 hours. After the reaction is completed, remove the solvent by evaporation. The crude product is purified by silica gel column chromatography (eluent: petroleum ether/EtOAc, 10:1) to obtain the target compound as a colorless oil, with a yield of 69.7%.

Product Advantages

 Privileged Benzoxazole Scaffold

The benzoxazole core of 2-Chlorobenzoxazole is a privileged heterocyclic scaffold in medicinal chemistry, appearing in numerous bioactive molecules with diverse pharmacological activities including antibacterial, antifungal, anticancer, and CNS agents.

 Versatile Reactive Handle

The chlorine substituent at the 2-position of 2-Chlorobenzoxazole serves as an excellent leaving group for nucleophilic aromatic substitution reactions with amines, alkoxides, and other nucleophiles. It also participates in palladium-catalyzed cross-coupling reactions, enabling the synthesis of diverse 2-substituted benzoxazole derivatives.

 Wide Range of Applications

2-Chlorobenzoxazole is utilized as a building block in pharmaceutical synthesis, agrochemical development, and the preparation of functional materials including fluorescent probes and organic electronic materials.

 Quality-Grade Intermediate

Cosperpharm supplies 2-Chlorobenzoxazole at >98% purity (GC) with identity confirmation by NMR, suitable for pharmaceutical intermediate manufacturing and research applications .

Storage Conditions

Store 2-Chlorobenzoxazole in a tightly sealed container under inert atmosphere (nitrogen or argon) at room temperature in a cool, dark place (<15°C) . Protect from air and moisture, as the compound is air sensitive . Keep away from strong oxidizing agents, strong bases, and sources of ignition.

Shelf life: Under recommended storage conditions, 2-Chlorobenzoxazole maintains quality for extended periods; however, due to its air sensitivity, inert atmosphere storage is critical.

Handling precautions: Use only in a fume hood. Wear chemical-resistant gloves (tested against EN 374 or equivalent), safety goggles, and a lab coat. Avoid generating dust or aerosols. Do not eat, drink or smoke in work areas. After handling, wash hands thoroughly. The compound is a combustible liquid—keep away from heat and open flames . Refer to the Safety Data Sheet (SDS) for complete safety information.

Contact Us

From heterocyclic synthesis to pharmaceutical intermediate manufacturing, your success depends on the quality of your building blocks. Cosperpharm delivers 2-Chlorobenzoxazole with the purity, stability, and supply reliability you need. Reach out to our team today to discuss your requirements.