17189-95-6

Basic information

• Product Name: 4-Phenyl-1,2-benzoquinone
• Synonyms: 4-Phenyl-1,2-benzoquinone;4-Phenyl-3,5-cyclohexadiene-1,2-dione
• CAS NO: 17189-95-6
• Molecular Formula: C₁₂H₈O₂
• Molecular Weight: 0
• Mol File: 17189-95-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Phenyl-1,2-benzoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenyl-1,2-benzoquinone(17189-95-6)
• EPA Substance Registry System: 4-Phenyl-1,2-benzoquinone(17189-95-6)

Safety Data

• Hazardous Substances Data: 17189-95-6(Hazardous Substances Data)

Upstream product

• 92-69-3 4-Phenylphenol 
• 92-05-7 3,4-dihydroxybiphenyl 

Downstream Products

• 92-05-7 3,4-dihydroxybiphenyl 

Relevant articles and documents

Dearomatization of Electron-Deficient Phenols to ortho-Quinones: Bidentate Nitrogen-Ligated Iodine(V) Reagents

Despite their broad utility, the synthesis of ortho-quinones remains a significant challenge, in particular, access to electron-deficient derivatives remains an unsolved problem. Reported here is the first general method for the synthesis of electron-deficient ortho-quinones by direct oxidation of phenols. The reaction is enabled by a novel bidentate nitrogen-ligated iodine(V) reagent, a previously unexplored class of compounds which we have termed Bi(N)-HVIs. The reaction is extremely general and proceeds with excellent regioselectivity for the ortho over para isomer. Functionalization of the ortho-quinone products was examined, resulting in a facile one-pot synthesis of catechols, as well as the incorporation of a variety of heteroatom nucleophiles. This method represents the first synthetic application of Bi(N)-HVIs and demonstrates their potential as a platform for the further development of highly reactive, but also highly tunable, I(V) reagents.

Multiple Electron Oxidation of Phenols by an Oxo Complex of Ruthenium(IV)

The kinetics of oxidation of phenol and alkylated phenol derivatives by (2+) and (2+) (bpy is 2,2'-bipyridine and py is pyridine) to give the corresponding quinones have been studied in aqueous solution and in acetonitrile.The reactions are first order in both phenol and Ru(IV)=O(2+) or Ru(III)-OH(2+).They proceed via a detectable intermediate, which is a Ru(II) complex. 18O isotopic labeling experiments show that transfer of the oxo group from Ru(IV)=O(2+) to phenol is quantitative.The reactions are facile.With Ru(IV)=O(2+) as oxidant k(25 deg C, CH3CN) = 1.9 (+/-0.4) E2M-1s-1; with Ru(III)-OH(2+) as oxidant k(25 deg C, CH3CN) = 4.0 (+/-0.4) E1M-1s-1.On the basis of the rate laws, the magnitude of OH/OD and CH/CD kinetic isotope effects, and the 18O labeling results, the most reasonable mechanisms for oxidation of phenol by Ru(IV)=O(2+) appears to be electrophilic attack on the aromatic ring.For Ru(III)-OH(2+), oxidation appears to occur by CH/H atom transfer in CH3CN and OH/H atom transfer in water.