2aminomethylphenol

2-aminomethylphenol is an aromatic organic compound with the formula C7H10NO. Its IUPAC name is 2-(aminomethyl)phenol and it is also known as 2-aminomethyl‑o‑phenol or o‑aminomethylphenol. The molecule has a molecular weight of 126.16 g mol⁻¹.

The compound is a pale brown liquid at room temperature that solidifies at about –40 °C. It has a faint phenolic odor and is moderately soluble in water, ethanol, and chloroform. The ortho position of the phenol ring relative to the amino‑methyl side chain gives it an intramolecular hydrogen‑bonding pattern that stabilizes the structure.

2‑Aminomethylphenol contains two functional groups: a phenolic hydroxyl and a primary amine. The proximity of these groups allows for multiple tautomeric forms and the ability to act as a bidentate ligand in coordination chemistry. The molecule is not chiral and exists as a single stereoisomer.

Industrial synthesis commonly proceeds by reductive amination of 2‑hydroxybenzaldehyde with formaldehyde and ammonia, or by the Hofmann rearrangement of the corresponding o‑hydroxybenzamide. In the laboratory a three‑step sequence involving diazotization of o‑aminophenyl methyl ketone followed by reduction is also used.

Applications include serving as an intermediate in the manufacture of azo dyes, as a precursor to pharmaceutical intermediates, and as a ligand for transition‑metal complexes used in catalysis. The compound’s dual donor sites make it useful in polymer chemistry for cross‑linking agents.

Safety data indicate that 2‑aminomethylphenol is an irritant to skin, eyes, and the respiratory tract. It should be handled in a well‑ventilated area with appropriate gloves and eye protection. Acute toxicity data are limited; chronic exposure may cause sensitisation. The substance is regulated under chemical safety frameworks that require proper labeling and handling instructions.