7437-73-2

Usage

Derivation

Derived from naphthalene, a widely used industrial chemical.

Composition

Consists of two benzoate groups attached to a 1,4-naphthalenediol molecule.

Industrial Applications

Crosslinking agent in the production of resins and coatings.
Stabilizer in plastics.
Component in the manufacturing of adhesives and sealants.

Role as an Intermediate

Used in the synthesis of various organic compounds, making it an important building block in the production of numerous industrial chemicals.

Upstream product

• 98-88-4 benzoyl chloride 
• 130-15-4 [1,4]naphthoquinone 
• 571-60-8 1,4-Dihydroxynaphthalene 

Downstream Products

• 97971-68-1 (3-benzoyl-1,4-dihydroxy-2-naphthyl)(phenyl)methanone 
• 97971-67-0 3-benzoyl-4-hydroxy-1-naphthyl benzoate 

Relevant academic research and scientific papers

Direct Synthesis of Hydroquinones from Quinones through Sequential and Continuous-Flow Hydrogenation-Derivatization Using Heterogeneous Au–Pt Nanoparticles as Catalysts

Pt–Au bimetallic nanoparticle catalysts immobilized on dimethyl polysilane (Pt–Au/(DMPSi-Al2O3)) have been developed for selective hydrogenation of quinones to hydroquinones. High reactivity, selectivity, and robustness of the catalysts were confirmed under continuous-flow conditions. Various direct derivatizations of quinones, such as methylation, acetylation, trifluoromethanesulfonylation, methacrylation, and benzoylation were successfully performed under sequential and continuous-flow conditions to afford the desired products in good to excellent yields. Especially, air-sensitive hydroquinones, such as anthrahydroquinones and naphthohydroquinones, could be successfully generated and derivatized under closed sequential and continuous-flow conditions without decomposition.

Photooxygenation of oxygen-substituted naphthalenes

The reaction of oxygen-substituted naphthalenes with singlet oxygen (1O2) has been investigated, and labile endoperoxides have been isolated and characterized at –78°C for the first time. Low-temperature kinetics by UV spectroscopy revealed that alkoxy and silyloxy substituents remarkably increase the rate of photooxygenations compared to 1,4-dimethylnaphthalene, whereas acyloxy-substituted acenes are inert towards 1O2. The reactivities nicely correlate with HOMO energies and free activation energies, which we determined by density functional theory calculations. The lability of the isolated endoperoxides is due to their very fast back reaction to the corresponding naphthalenes even at –20°C under release of 1O2, making them to superior sources of this reactive species under very mild conditions. Finally, a carbohydrate-substituted naphthalene has been synthesized, which reacts reversibly with 1O2 and might be applied for enantioselective oxidations in future work.