54210-12-7

Basic information

• Product Name: 3,5-Cyclohexadiene-1,2-dione,4-(1-methylethyl)-(9CI)
• Synonyms: 3,5-Cyclohexadiene-1,2-dione,4-(1-methylethyl)-(9CI)
• CAS NO: 54210-12-7
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.1745
• Product Categories: ISOPROPYL
• Mol File: 54210-12-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,5-Cyclohexadiene-1,2-dione,4-(1-methylethyl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Cyclohexadiene-1,2-dione,4-(1-methylethyl)-(9CI)(54210-12-7)
• EPA Substance Registry System: 3,5-Cyclohexadiene-1,2-dione,4-(1-methylethyl)-(9CI)(54210-12-7)

Safety Data

• Hazardous Substances Data: 54210-12-7(Hazardous Substances Data)

Upstream product

• 99-89-8 4-Isopropylphenol 
• 75-91-2 tert.-butylhydroperoxide 
• 2138-43-4 4-isopropylcatechol 

Relevant articles and documents

A Catalyst-Controlled Aerobic Coupling of ortho-Quinones and Phenols Applied to the Synthesis of Aryl Ethers

ortho-Quinones are underutilized six-carbon-atom building blocks. We herein describe an approach for controlling their reactivity with copper that gives rise to a catalytic aerobic cross-coupling with phenols. The resulting aryl ethers are generated in high yield across a broad substrate scope under mild conditions. This method represents a unique example where the covalent modification of an ortho-quinone is catalyzed by a transition metal, creating new opportunities for their utilization in synthesis.

Dirhodium-catalyzed phenol and aniline oxidations with T-HYDRO. Substrate scope and mechanism of oxidation

Dirhodium caprolactamate, Rh2(cap)4, is a very efficient catalyst for the generation of the tert-butylperoxy radical from tert-butyl hydroperoxide, and the tert-butylperoxy radical is a highly effective oxidant for phenols and anilines. These reactions are performed with 70% aqueous tert-butyl hydroperoxide using dirhodium caprolactamate in amounts as low as 0.01 mol % to oxidize para-substituted phenols to 4-(tert-butyldioxy) cyclohexadienones. Although these transformations have normally been performed in halocarbon solvents, there is a significant rate enhancement when Rh 2(cap)4-catalyzed phenol oxidations are performed in toluene or chlorobenzene. Electron-rich and electron-poor phenolic substrates undergo selective oxidation in good to excellent yields, but steric influences from bulky para substituents force oxidation onto the ortho position resulting in ortho-quinones. Comparative results with RuCl2(PPh 3)3 and CuI are provided, and mechanistic comparisons are made between these catalysts that are based on diastereoselectivity (reactions with estrone), regioselectivity (reactions with p-tert-butylphenol), and chemoselectivity in the formation of 4-(tert-butyldioxy)cyclohexadienones. The data obtained are consistent with hydrogen atom abstraction by the tert-butylperoxy radical followed by radical combination between the phenoxy radical and the tert-butylperoxy radical. Under similar reaction conditions, para-substituted anilines are oxidized to nitroarenes in good yield, presumably through the corresponding nitrosoarene, and primary amines are oxidized to carbonyl compounds by TBHP in the presence of catalytic amounts of Rh 2(cap)4.

Removal of p-alkylphenols from aqueous solutions by combined use of mushroom tyrosinase and chitosan beads

Enzymatic removal of p-alkylphenols from aqueous solutions was investigated through the two-step approach, the quinone conversion of p-alkylphenols with mushroom tyrosinase (EC 1.14.18.1) and the subsequent adsorption of quinone derivatives enzymatically