5664-33-5

Usage

Uses

Used in Organic Synthesis Industry:
Cyclohexa-2,5-dien-1-one is used as a raw material for the production of various organic compounds. Its reactivity and strong carbon acidity make it a valuable component in the synthesis of a wide range of chemical products.
Used in Research Applications:
Due to its reactivity, cyclohexa-2,5-dien-1-one is employed as a research compound in various scientific studies. It is used to explore new chemical reactions, mechanisms, and the development of novel synthetic pathways.
Used in Chemical Education:
Cyclohexa-2,5-dien-1-one is utilized as a teaching aid in chemical education, helping students understand the principles of organic chemistry, reactivity, and the properties of aromatic compounds.
Used in Safety Training:
Given its volatility and potential hazards, cyclohexa-2,5-dien-1-one is also used in safety training programs to educate chemists and laboratory personnel on the proper handling and storage of reactive and volatile chemicals.

Upstream product

• 89713-14-4 4-diazo-2,5-cyclohexadienone 
• 108-95-2 phenol 
• 74428-26-5 4,4a,8,8a-Tetrahydro-1H-1,4-methano-naphthalen-5-one 

Downstream Products

• 13021-19-7 4,4-dimethoxy-1,1':4',1-terphenyl 
• 3769-82-2 2-(4-nitrophenyl)-1-phenylethanone 
• 2206-94-2 1-acetoxy-1-phenylethene 
• 93413-62-8 O-desmethylvenlafaxine 
• 94459-01-5 4-<<4-(allyloxy)benzoyl>oxy>-4'-methoxy-p-terphenyl 
• 94459-00-4 4''-methoxy-1,1':4',1''-terphenyl-4-ol 
• 108-95-2 phenol 

Relevant academic research and scientific papers

Facile synthesis of monodisperse Ag@C@Ag core-double shell spheres for application in the simultaneous sensing of thymol and phenol

A simple coupled synthesis and encapsulation route was developed to fabricate monodisperse, uniform Ag@C@Ag core-shell structured nanocomposites with excellent electrochemical and catalytic properties, in which Ag nanoparticles were first encapsulated in a carbonaceous shell through the catalyzed dehydration of glucose under hydrothermal conditions, and then the surface-activated Ag@C spheres were subsequently used to accumulate [Ag(NH3)2]+ or Ag+ ions through electrostatic attraction to anchor the Ag coating. The as-prepared nanocomposites were demonstrated to have a great potential for the simultaneous multiplexed detection of thymol and phenol, and exhibited high sensitivity and good reproducibility. In addition, the practical analytical application of the sensing platform was assessed by the determination of thymol and phenol in real honey samples, and satisfactory results were achieved.

Electrochemical detection of hydroquinone by graphene and Pt-graphene hybrid material synthesized through a microwave-assisted chemical reduction process

We have synthesized graphene and Pt-graphene hybrid material by a microwave-assisted chemical reduction process and evaluated their application as electrode materials towards the electrochemical detection of hydroquinone. Graphene modified glass carbon electrode (GCE) showed a good performance for detecting hydroquinone due to the unique properties of graphene which increased the active surface area of the electrode and accelerated the electron transfer. The linear detection range of hydroquinone concentration was 20-115 μM with a sensitivity of 1.38 μA μM-1 cm-2; the detection limit was estimated to be 12 μM (S/N = 3). The electrocatalytic activity of the Pt-graphene modified GCE was further improved due to the enhanced electron transfer and the linear detection range was 20-145 μM with the sensitivity of 3.56 μA μM-1 cm-2, detection limit 6 μM (S/N = 3).

Al2O3 surface complexation for photocatalytic organic transformations

The use of sunlight to drive organic reactions constitutes a green and sustainable strategy for organic synthesis. Herein, we discovered that the earth-abundant aluminum oxide (Al2O3) though paradigmatically known to be an insulator could induce an immense increase in the selective photo-oxidation of different benzyl alcohols in the Presence of a large variety of dyes and O2. This unique phenomenon is based on the surface complexation of benzyl alcohol (BnOH) with the Brensted base sites on Al2O3, which reduces its oxidation potential and causes an upshift in its HOMO for electron abstraction by the dye. The surface complexation of O2 with Al2O3 also activates the adsorbed O2 for receiving electrons from the photoexcited dyes. This discovery brings forth a new understanding on utilizing surface complexation mechanisms between the reactants and earth abundant materials to effectively achieve a wider range of photoredox reactions.

Deuterium and hydrogen tunneling in the hydrogenation of 4-oxocyclohexa-2,5-dienylidene

4-Oxocyclohexa-2,5-dienylidene is a highly reactive triplet ground state carbene that is hydrogenated in solid H2, HD, and D2 at temperatures as low as 3 K. The mechanism of the insertion of the carbene into dihydrogen was investigated by IR and EPR spectroscopy and by kinetic studies. H or D atoms were observed as products of the reaction with H2 and D2, respectively, whereas HD produces exclusively D atoms. The hydrogenation shows a very large kinetic isotope effect and remarkable isotope selectivity, as was expected for a tunneling reaction. The experiments, therefore, provide clear evidence for both hydrogen tunneling and the rare deuterium tunneling in an intermolecular reaction. Tunnel beats mountain pass: Triplet oxocyclohexadienylidene readily reacts with H2, HD, and even D2 at 3 K by a tunneling reaction. The experiments provided clear evidence for both hydrogen tunneling and the rare deuterium tunneling in an intermolecular reaction (see figure).

Ketonization equilibria of phenol in aqueous solution

The two keto tautomers of phenol (1), cyclohexa-2,4-dienone (2) and cyclohexa-2,5-dienone (3), were generated by flash photolysis of appropriate precursors in aqueous solution, and the pH-rate profiles of their enolization reactions, 2 → 1 and 3 → 1, were measured. The rates of the reverse reactions, 1 → 2 and 1 → 3, were determined from the rates of acid-catalyzed hydron exchange at the ortho- and para-positions of 1; the magnitude of the kinetic isotope effect was assessed by comparing the rates of hydrogenation of phenol-2t and -2d. The ratios of the enolization and ketonization rate constants provide the equilibrium constants of enolization, pKE(2, aq, 25°C) = -12.73 ± 0.12 and pKE(3, aq, 25°C) = -10.98 ± 0.15. Combination with the acidity constant of phenol also defines the acidity constants of 2 and 3 through a thermodynamic cycle. These ketones are remarkably strong carbon acids: pKa(2) = -2.89 ± 0.12 and pKa(3) = -1.14 ± 0.15. They disappear by proton transfer to the solvent with lifetimes, τ(2) = 260 μs and τ(3) = 13 ms, that are insensitive to pH in the range from 3-10.

REACTIONS RETRODIENIQUES - X. OBTENTION PAR REACTION DE RETRO-DIELS-ALDER DE CETONES TAUTOMERES DE PHENOLS.

Several unstable ketones, tautomers of phenols, have been obtained by flash thermolysis of Diels-Alder adducts and identified by their IR and UV spectra at -196 deg C.