Aminomethylphenol

Aminomethylphenol is an aromatic organic compound containing a phenolic hydroxyl group and an aminomethyl side chain. The most common isomer is 4‑aminomethylphenol (also known as para‑aminomethylphenol), which has the molecular formula C7H9NO and a molar mass of 119.15 g mol⁻¹. It appears as a colorless to pale yellow crystalline solid that is only sparingly soluble in water but readily dissolves in ethanol, acetone and other polar organic solvents. The compound melts at approximately 123 °C and has a slightly bitter, phenolic odor.

The synthesis of 4‑aminomethylphenol is typically achieved by the reductive amination of 4‑nitrobenzyl alcohol followed by conversion of the nitro group to an amino group. Alternative routes include the acid‑catalyzed addition of ammonia to 4‑hydroxybenzaldehyde to give 4‑aminobenzylalcohol, which can then be oxidized to the corresponding nitro compound and reduced. In laboratory settings, the most convenient method is often the three‑step sequence of benzyl protection, hydroxylation, and reductive amination, yielding the product in 65–75 % isolated yield.

Aminomethylphenol serves as a versatile ligand in coordination chemistry, where it can bind metal centers through both the oxygen of the phenol and the nitrogen of the amino group, forming chelate rings. It is also employed as an intermediate in the synthesis of certain dyestuffs and pharmaceuticals, as well as a building block for heterocyclic compounds. In industrial contexts, small quantities of the compound are used as a chromatographic reagent and as a flavor additive in specialty vinyl material.

Handling precautions indicate that the compound can irritate skin and mucous membranes; therefore, personal protective equipment such as gloves and eye protection is recommended. A container label should warn against inhalation, ingestion and potential contact with combustible materials.