3hydroxybenzonitrile

3hydroxybenzonitrile, also known as m-hydroxybenzonitrile or 3-cyanophenol, is an organic compound with the chemical formula C₇H₅NO. It belongs to the class of aromatic nitriles, characterized by a cyano group (–CN) attached to a benzene ring with a hydroxyl group (–OH) at the meta position (position 3). The compound appears as a white to off-white crystalline solid with a faint aromatic odor.

Synthesis of 3hydroxybenzonitrile typically involves the nitration of phenol followed by reduction and subsequent cyanation. Alternatively, it can be prepared through the Sandmeyer reaction starting from m-aminophenol. The compound is moderately soluble in organic solvents like ethanol and ether but has limited solubility in water.

3hydroxybenzonitrile exhibits properties typical of phenolic compounds, including weak acidity due to the hydroxyl group. It can undergo electrophilic aromatic substitution reactions, though the hydroxyl substituent deactivates the ring toward further substitution. The cyano group contributes to its reactivity, allowing for nucleophilic addition reactions under certain conditions.

Applications of 3hydroxybenzonitrile are limited but include use as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals. Its phenolic nature makes it useful in the production of dyes, fragrances, and certain functional materials. Due to its potential toxicity, handling requires appropriate safety measures, including gloves and ventilation.

The compound is stable under normal conditions but may decompose upon exposure to strong acids, bases, or high temperatures. Storage should be in a cool, dry environment away from incompatible substances. Research on its biological activity remains limited, though studies suggest it may exhibit antioxidant properties similar to other phenolic compounds.