15232-10-7

Usage

Uses

Used in Polymer and Resin Production:
2,5-Cyclohexadiene-1,4-dione, 2-(1-methylethyl)is used as a key precursor in the production of polymers and resins. Its chemical properties allow it to be incorporated into the structures of these materials, enhancing their performance characteristics such as durability, flexibility, and resistance to environmental factors.
Used in Adhesive Manufacturing:
In the adhesive industry, 2,5-Cyclohexadiene-1,4-dione, 2-(1-methylethyl)is utilized as an intermediate to formulate adhesives with improved bonding strength and stability. Its reactivity contributes to the creation of strong cross-linkages within the adhesive matrix, ensuring robust adhesion to various substrates.
Used in Pharmaceutical Synthesis:
2,5-Cyclohexadiene-1,4-dione, 2-(1-methylethyl)is employed as an intermediate in the synthesis of pharmaceuticals. Its unique structure allows it to be a building block for the development of new drugs, potentially contributing to the discovery of novel therapeutic agents with diverse applications in medicine.
Used in Agrochemical Production:
In the agrochemical sector, 2,5-Cyclohexadiene-1,4-dione, 2-(1-methylethyl)is used as a starting material for the synthesis of various agrochemicals. Its involvement in the production process helps in the development of effective pesticides, herbicides, and other agricultural chemicals that protect crops and enhance agricultural productivity.

Upstream product

• 88-69-7 2-(1-methylethyl)phenol 
• 99-98-9 4-amino-N,N-dimethylaniline 
• 75-30-9 2-iodo-propane 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 106-51-4 p-benzoquinone 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 57727-06-7 2-(isopropoxy)-2-oxoacetic acid 
• 79-31-2 isobutyric Acid 
• 312264-19-0 isopropyl p-methylphenyl telluride 
• 98-82-8 Isopropylbenzene 
• 4132-71-2 2-Isopropyl-1,4-dimethoxybenzene 

Downstream Products

• 2349-71-5 2-isopropylhydroquinone 

Relevant academic research and scientific papers

Progress towards metal-free radical alkylations of quinones under mild conditions

A new method for the radical alkylation of quinones is reported. Lewis basic nitrogen additives increase the efficacy of quinone alkylations from carboxylic acids using catalytic AgNO3 and Selectfluor as a mild oxidant. Electrochemical data sug

Radical-mediated synthesis of substituted quinones with organotellurium compounds

Carbon-centered radicals generated from the corresponding organotellurium compounds react with a variety of quinones under photo-thermal conditions to give the monoaddition product in good to excellent yield. The reaction can be used for the synthesis of polyprenyl quinoid natural products.

Quinone C-H Alkylations via Oxidative Radical Processes

A brief survey of radical additions to quinones is reported. Carboxylic acids, aldehydes, and unprotected amino acids are compared as alkyl radical precursors for the mono- or bis- C-H alkylation of several quinones. Two methods for radical initiation are discussed comparing inorganic persulfates and Selectfluor as stoichiometric oxidants. Kinetic analysis reveals dramatic differences in the rate of radical initiation depending on the identity of the radical precursor and oxidant. Synthetic strategies for efficiently producing alkyl-quinones are discussed in the context of selecting optimum radical precursors and initiators depending on quinone identity and functional groups present.

Silver-Catalyzed Minisci Reactions Using Selectfluor as a Mild Oxidant

A new method for silver-catalyzed Minisci reactions using Selectfluor as a mild oxidant is reported. Heteroarenes and quinones both participate in radical C-H alkylation and arylation from a variety of carboxylic and boronic acid radical precursors. Several oxidatively sensitive and highly reactive radical species are successful, providing structures that are challenging to access by other means.

Catalytic asymmetric [2+2] cycloaddition between quinones and fulvenes and a subsequent stereoselective isomerization to 2,3-dihydrobenzofurans

The catalytic enantioselective [2+2] cycloaddition between quinones and fulvenes was achieved, for the first time, by the use of a chiral copper(ii) complex catalyst. The transformation afforded a series of enantiomerically enriched [6,4,5]-tricyclic cyclobutane derivatives in good yields with excellent regio- and stereoselectivities. Furthermore, the [2+2] adducts could be easily converted into formal [3+2] adducts efficiently and stereoselectively.

Chiral cobalt(II) complex catalyzed Friedel-Crafts aromatization for the synthesis of axially chiral biaryldiols

An efficient atroposelective synthesis of axially chiral biaryldiols via asymmetric Friedel-Crafts aromatization between p-quinones and 2-naphthols was developed. A chiral cobalt(ii) complex of N,N′-dioxide enabled the process to generate axially chiral biaryldiols in up to 98% yield and 95% ee. A large range of substituents at different positions of p-quinones and 2-naphthols was tolerable. The configuration of the product and the chiral N,N′-dioxide-Co(ClO4)2 catalyst was identified by X-ray crystal diffraction analysis and a possible catalytic model was suggested.

Substituent effects in the oxidation of 2-alkyl-1,4-dialkoxybenzenes with ceric ammonium nitrate

Increased steric size of alkyl groups and the presence of coordinating atoms on alkoxy groups have both been found to contribute to decreasing yields of diquinones upon reaction of 2-alkyl-1,4-dialkoxybenzenes with CAN. The overall hydrophilicity of the substrates does not appear to be a significant factor in determining the diquinone yield for these reactions.

Chemo- and regioselective direct hydroxylation of arenes with hydrogen peroxide catalyzed by a divanadium-substituted phosphotungstate

Peroxide in, phenol out: The catalyst [-PW10O38V 2(μ-OH)2]3- showed high activity in the hydroxylation of various aromatic compounds with aqueous H2O 2. The system was regioselective, producing para-phenols from monosubstituted benzene derivatives. Furthermore, alkylarenes with reactive side-chain Ca spa 3-H bonds could be chemoselectively hydroxylated without significant formation of side-chain oxygenated products. Copyright

Ruthenium-catalyzed oxidative dearomatization of phenols to 4-(tert-butylperoxy)cyclohexadienones: Synthesis of 2-substituted quinones from p-substituted phenols

The ruthenium-catalyzed oxidation of phenols with tert-butylhydroperoxide efficiently gives the corresponding 4-(tert-butylperoxy)cyclohexadienones. The oxidation proceeds selectively because of ruthenium's ability for rapid single-electron transfer. This biomimetic oxidation reaction is highly useful to obtain the metabolic compounds desired for confirming the safety of medicines and related compounds. Typically, the first metabolic compound of the female hormone estrone is readily obtained by this biomimetic oxidation reaction. The resulting 4-(tert-butylperoxy)cyclohexadienones are versatile synthetic intermediates, which can be transformed into 2-substituted 1,4-benzoquinones by treatment with acid catalysts. Acid-promoted rearrangement followed by a Diels-Alder reaction provides a new strategy for the synthesis of fused cyclic compounds, such as naphthoquinone and anthraquinone derivatives, from readily available phenols. The nonnatural 1,4-diacetoxy steroidal skeleton is obtained by the oxidation of estrone followed by zinc-mediated migration. Vitamin K 3 is synthesized selectively from p-cresol in an overall 79 % yield in 4 steps, and the synthesis includes the ruthenium-catalyzed oxidation.

Synthesis of 2-substituted quinones, vitamin K3, and vitamin K1 from p-cresol. BF3·OEt2-catalyzed methyl migration of 4-tert-butyldioxycyclohexadienones

BF3·OEt2-catalyzed methyl group migration of 4-methyl-4-tert-butyldioxycyclohexadienone, which is obtained by ruthenium-catalyzed oxidation of p-cresol with tert-butyl hydroperoxide, in hexafluoro-2-propanol/toluene gave toluquinone efficiently. The reaction can be applied to the regio-selective short-step syntheses of vitamin K3 and vitamin K1 from p-cresol.