3Hydroxyaniline

3-Hydroxyaniline, or m-hydroxyaniline, is an aromatic amine and phenol derivative. Its structure features a benzene ring bearing an amino group (–NH2) at position 1 and a hydroxyl group (–OH) at position 3. The empirical formula is C6H7NO, and the molecular weight is about 109.1 g/mol. It is a colorless to light yellow solid that is moderately soluble in water and soluble in many organic solvents. The compound participates in hydrogen bonding due to the amino and hydroxyl groups, influencing its physical properties and reactivity.

In industry, 3-hydroxyaniline is used chiefly as an intermediate in the synthesis of dyes, especially azo dyes, as well as in the preparation of pharmaceuticals and other organic intermediates that require meta-substituted aniline motifs. It can serve as a building block for more complex molecules where the meta relationship between amino and hydroxy groups influences subsequent reactions.

Synthesis routes typically involve functionalization of the aromatic ring to install both the amino and hydroxyl substituents in the meta relationship, or transformation of related precursors. Handling requires standard precautions for aromatic amines and phenols: they can be irritants and may be hazardous if inhaled, swallowed, or absorbed through skin. Appropriate engineering controls, PPE, and waste management are recommended.

Related compounds include o-hydroxyaniline (2-hydroxyaniline) and p-hydroxyaniline (4-hydroxyaniline), which differ in the relative positions of the hydroxy group and amino group and exhibit different physical properties and reactivities.