17660-74-1

Basic information

• Product Name: Bicyclo[2.2.2]oct-2-ene-5,7-dione
• Synonyms: Bicyclo[2.2.2]oct-2-ene-5,7-dione;Bicyclo[2.2.2]oct-7-ene-2,5-dione
• CAS NO: 17660-74-1
• Molecular Formula: C₈H₈O₂
• Molecular Weight: 0
• Mol File: 17660-74-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Bicyclo[2.2.2]oct-2-ene-5,7-dione(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.2]oct-2-ene-5,7-dione(17660-74-1)
• EPA Substance Registry System: Bicyclo[2.2.2]oct-2-ene-5,7-dione(17660-74-1)

Safety Data

• Hazardous Substances Data: 17660-74-1(Hazardous Substances Data)

Upstream product

• 61543-84-8 (+/-)-5,7-dioxobicyclo<2.2.2>octane-2,3-dicarboxylic acid 
• 61543-84-8 5,7-dioxobicyclo<2.2.2>octane-2,3-dicarboxylic acid 
• 67209-59-0 5-hydroxybicyclo[2.2.2]oct-7-en-2-one 
• 123-31-9 hydroquinone 
• 6537-90-2 (+/-)-5,7-dioxobicyclo<2.2.2>octane-2,3-dicarboxylic anhydride 
• 108-31-6 maleic anhydride 

Downstream Products

• 113948-12-2 C₂₄H₂₂⁽²⁾H₂O₄S₂ 
• 61543-85-9 Bicyclo<2.2.2>oct-7-en-2,5-dion-bis(tosylhydrazon) 
• 108-95-2 phenol 
• 108-95-2 phenol radical cation 
• 24599-57-3 1,3-cyclohexadien-5-one radical cation 
• 24599-57-3 1,3-cyclohexadiene monoxide 
• 67209-52-3 Bicyclo<2.2.2>octa-5,7-dien-2-on 
• 130913-08-5 (1R,4R,5R)-5-Phenyl-bicyclo[2.2.2]octan-2-one 
• 130913-08-5 (1R,4R,5S)-5-Phenyl-bicyclo[2.2.2]octan-2-one 
• 130913-05-2 C₁₆H₂₀O₃ 
• 130913-06-3 (1R,4R)-5-Hydroxy-5-phenyl-bicyclo[2.2.2]octan-2-one 
• 132486-17-0 (1R,4R)-5-phenylbicyclo[2.2.2]oct-5-en-2-one 
• 130913-09-6 (R)-2-Phenyl-bicyclo[2.2.2]octane 

Relevant articles and documents

-

-

LOW-MOLECULAR COMPOUND, POLYMER, MATERIAL FOR ELECTRONIC DEVICES, COMPOSITION FOR ELECTRONIC DEVICES, ORGANIC ELECTROLUMINESCENT ELEMENT, ORGANIC SOLAR CELL ELEMENT, DISPLAY AND LIGHTING EQUIPMENT

A subject for the invention is to provide compounds where a film formation can be made by a wet film formation method, a heating temperature at the film formation is low, the film formed therefrom has high stability, and the other layers can be laminated thereon by a wet film formation method or another method. The compounds are usable as a material for electronic device which decreases little in charge transport efficiency or luminescent efficiency and which have excellent driving stability. The invention resides in a compound and a polymer which are characterized by having a elimination group of a specific structure and in an organic compound characterized by having a elimination group having a low elimination temperature.

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.