3aminophenols

3-Aminophenol, also known as meta-aminophenol or m-aminophenol, is an aromatic amine bearing an amino group at the 3-position relative to a hydroxyl group on a benzene ring. The combination of amine and phenolic functionality gives it distinct reactivity compared with the o- and p-aminophenol isomers.

Isomerism in aminophenols includes the ortho (2-), meta (3-), and para (4-) forms. Meta-aminophenol is used as an intermediate in organic synthesis, particularly in the preparation of dyes, pigments, and some pharmaceutical and polymer-related compounds.

Production and routes: industrial routes for m-aminophenol typically involve the reduction of 3-nitrophenol or related 3-nitroaryl derivatives. In some processes, nitration of phenol followed by separation can yield meta-nitrophenol, which is then reduced to the corresponding amine. Routes are chosen to optimize yield, purity, and cost, and may include protecting-group strategies or sequence adjustments to minimize isomeric mixtures.

Applications: m-Aminophenol serves as a building block for azo dyes and as an intermediate in the synthesis of specialty chemicals, including certain antioxidants and pharmaceutical precursors. Its reactivity as both a phenol and an amine enables diverse coupling and substitution reactions.

Properties: It is a crystalline solid or pale-yellow material that is moderately soluble in water. The amino group imparts basic character, and the compound can act as a nucleophile in electrophilic aromatic substitution and related reactions. It is typically handled under standard safety precautions for aminophenols, with awareness of irritation and potential environmental impact.

Safety: 3-Aminophenol is considered hazardous; it can irritate skin, eyes, and the respiratory tract and should be handled in a well-ventilated area with appropriate personal protective equipment. Environmental release should be minimized.