14Naphthoquinone

14naphthoquinone is commonly known in standard nomenclature as 1,4-naphthoquinone. The nonstandard form 14-naphthoquinone may appear in some literature, but the accepted name for the compound is 1,4-naphthoquinone. Its molecular formula is C10H6O2, and it consists of a naphthalene skeleton bearing two carbonyl groups at positions 1 and 4, giving a planar, conjugated quinone system. It is a pale orange solid that dissolves in many organic solvents and is sparingly soluble in water. The melting point is typically reported around 125–126 °C.

It is commercially produced by oxidizing naphthalene or certain naphthalene derivatives. Various oxidation routes exist, often employing reagents such as nitric acid or metal-based catalysts to yield the 1,4-dione. It is not a natural product in any substantial sense but can be prepared from readily available precursors for use in pigments and chemical industries.

As a quinone, 1,4-naphthoquinone is a reactive, redox-active compound. It can participate in nucleophilic additions and Michael-type reactions and can undergo redox cycling, acting as an electron acceptor in organic reactions and electrochemical applications. The compound is sensitive to strong reducing environments and can be reduced to hydroquinone derivatives.

Applications of 1,4-naphthoquinone include its use as a building block in the synthesis of dyes, pharmaceuticals, and organic semiconductors. It serves as an intermediate in the preparation of naphthoquinone-based pigments and various heterocyclic compounds.

Safety considerations are important: 1,4-naphthoquinone is a hazardous chemical that can irritate skin and eyes and can be harmful if inhaled or ingested. It should be handled with appropriate safety precautions, including gloves and adequate ventilation, and stored away from incompatible reducers and oxidants.