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Isobenzofuran

Updated: 2026-08-14

Overview

Isobenzofuran is a bicyclic heteroaromatic compound consisting of a fused benzene and furan ring. It is a reactive intermediate widely used in organic synthesis, particularly in the production of pharmaceuticals and specialty chemicals. Due to its diene character, isobenzofuran participates in cycloaddition reactions like the Diels-Alder reaction, making it valuable for constructing complex molecular frameworks. Commercial availability is typically limited to small quantities for research purposes.

Physical and Chemical Properties

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Isobenzofuran is a volatile, low-melting solid or liquid at room temperature, depending on purity. Its conjugated π-electron system gives it characteristic UV absorption at ~290 nm. The compound exhibits high reactivity due to its strained structure and electron-rich furan ring. It polymerizes readily upon exposure to air or light, necessitating stabilization with antioxidants like BHT during storage. Its solubility profile favors organic solvents, with limited stability in aqueous environments.

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Main Applications

In pharmaceutical synthesis, isobenzofuran serves as a precursor to anticoagulants, antipsychotics, and other bioactive molecules. Its ability to form adducts with electron-deficient dienophiles enables efficient construction of polycyclic structures. The agrochemical industry utilizes derivatives for crop protection agents. Additionally, it finds niche applications in materials science for creating conjugated polymers with optoelectronic properties.

Safety and Storage

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As a flammable and reactive compound, isobenzofuran requires careful handling under inert atmosphere (nitrogen/argon). Storage at 2-8°C in amber glass with oxygen scavengers prolongs shelf life. Personal protective equipment (PPE) including nitrile gloves and splash goggles is mandatory. Spills should be absorbed with inert material and disposed as hazardous waste. Never expose to strong oxidizers due to fire/explosion risk.

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B2B Procurement Guide

Industrial buyers should prioritize suppliers offering stabilized formulations with certificates of analysis (CoA). Bulk purchases (>1kg) typically require custom synthesis arrangements. Key procurement considerations include: batch-to-batch consistency, HPLC purity verification, and supplier capability for hazardous material transportation. Lead times may extend to 4-6 weeks for customized orders. Consider establishing long-term contracts with qualified producers to ensure supply chain stability.

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