30237-07-1

Usage

Uses

Used in Organic Synthesis:
2-(p-tolyl)-p-benzoquinone is used as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure and reactivity make it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used as a Reagent in Chemical Reactions:
In the field of chemistry, 2-(p-tolyl)-p-benzoquinone serves as a reagent, facilitating a range of chemical transformations. Its ability to act as an oxidizing agent is particularly useful in processes that require the introduction of oxygen atoms into organic substrates.
Used in the Production of Dyes and Pigments:
2-(p-tolyl)-p-benzoquinone is utilized in the manufacturing of dyes and pigments due to its color-producing properties. Its yellow crystalline nature contributes to the coloration of various products, making it an essential ingredient in the dye and pigment industry.
Used in Pharmaceutical Applications:
2-(p-tolyl)-p-benzoquinone finds use in pharmaceutical applications, where it may be employed as an active pharmaceutical ingredient or as a precursor in the synthesis of drugs. Its potential in medicinal chemistry is attributed to its ability to interact with biological systems, offering opportunities for the development of new therapeutic agents.
Used in Materials Science:
In the realm of materials science, 2-(p-tolyl)-p-benzoquinone is explored for its potential applications in the development of new materials with unique properties. Its chemical structure and reactivity may contribute to the creation of advanced materials with applications in various industries, including electronics, energy, and environmental technologies.

InChI:InChI=1/C13H10O2/c1-9-2-4-10(5-3-9)12-8-11(14)6-7-13(12)15/h2-8H,1H3

Upstream product

• 10557-67-2 N-nitroso-p-methyl-acetanilide 
• 106-51-4 p-benzoquinone 
• 10551-32-3 (4-methylphenyl)-hydroquinone 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 123-31-9 hydroquinone 
• 75-30-9 2-iodo-propane 
• 583-63-1 ortoquinone 
• 106-49-0 p-toluidine 
• 5720-05-8 4-methylphenylboronic acid 
• 624-31-7 4-tolyl iodide 
• 539-44-6 N-4-methylphenylhydrazine 
• 108-88-3 toluene 
• 123726-16-9 bis(4-methylphenyl)iodonium trifluoromethanesulfonate 
• 120976-84-3 phenyl(p-tolyl)iodonium trifluoromethanesulfonate 

Downstream Products

• 60544-08-3 2-(4-methylphenyl)naphthalene-1,4-dione 
• 10551-32-3 (4-methylphenyl)-hydroquinone 
• 132782-83-3 1,3-Diphenyl-6-p-tolyl-1H-indazole-4,7-dione 
• 132782-89-9 (3aS,8aR)-1,3,5,7-Tetraphenyl-8a-p-tolyl-3a,8a-dihydro-1H,7H-benzo[1,2-c;5,4-c']dipyrazole-4,8-dione 
• 132782-84-4 3-(4-Chloro-phenyl)-1-phenyl-6-p-tolyl-1H-indazole-4,7-dione 
• 132782-90-2 (3aS,8aR)-3,5-Bis-(4-chloro-phenyl)-1,7-diphenyl-8a-p-tolyl-3a,8a-dihydro-1H,7H-benzo[1,2-c;5,4-c']dipyrazole-4,8-dione 
• 299174-64-4 3-p-tolyl-2,5-bis-p-tolylamino-[1,4]benzoquinone 
• 299174-63-3 2,5-bis-phenylamino-3-p-tolyl-[1,4]benzoquinone 
• 327078-57-9 5-hydroxy-7-(4-methylphenyl)-1,3-benzoxathiole-2-one 
• 325748-75-2 5-hydroxy-7-(4-methylphenyl)-1,3-benzoxathiole-2-thione 
• 107522-62-3 1,4-dihydroxy-3-p-tolyl-[2]naphthonitrile 
• 101606-82-0 1,4-dioxo-3-p-tolyl-1,4-dihydro-[2]naphthonitrile 

Relevant academic research and scientific papers

Metal-free, air-promoted, radical-mediated arylation of benzoquinone with phenylhydrazines

An efficient, economic, and air-promoted metal-free method for direct arylation of benzoquinone with phenylhydrazines was developed. This approach leads to the formation of corresponding [1,1′-biphenyl]-2,5-dione derivatives as biological and pharmaceutic

Ir-catalyzed arylation, alkylation of quinones with boronic acids through C-C coupling

Ir-catalyzed arylation, alkylation of quinones with boronic acids was developed under room temperature. Both aryl and alkyl boronic acids are suitable for this transformation. This expands the application scope of the iridium catalyst. This is also an excellent proof that iridium catalysts can be used in the C-C coupling of quinones and naphthoquinones with alkyl boronic acids.

Synthesis of aryl substituted quinones as β-secretase inhibitors: Ligand-free direct arylation of quinones with aryl halides

The simple ligand-free direct arylation of quinones with aryl halides applying Pd(OAc)2as a catalyst in accordance with Heck reaction was studied. This reaction provided a simple and efficient synthetic approach to efficient inhibitors of β-secretase aryl-substituted quinones.

Transition metal-free direct C-H functionalization of quinones and naphthoquinones with diaryliodonium salts: Synthesis of aryl naphthoquinones as β-secretase inhibitors

A novel ligand-free, transition metal-free direct C.H functionalization of quinones with diaryliodonium salts has been developed for the first time. The transformation was promoted only through the use of a base and gave aryl quinone derivatives in moderate to good yields. This methodology provided an effective and easy way to synthesize β-secretase inhibitors. The radical trapping experiments showed that this progress was the radical mechanism.

Generation of arylated quinones by iron-catalyzed oxidative arylation of phenols: Formal synthesis of phellodonin, sarcodonin ε, leucomelone and betulinan A

Biologically and pharmaceutically relevant arylated quinones (Quin-Ar) have been synthesized via direct C-H arylation of a variety of phenols using arylboronic acids. An inexpensive, environmentally friendly iron catalyst, ferric sulphate, Fe2(SO4)3, was employed in this operationally simple and efficient method.

Synthesis of aryl- and alkylquinones through rhodium-catalyzed C-C coupling under mild conditions

A direct arylation, alkylation of quinones with aryl and alkyl boronic acids through rhodium-catalyzed C-C coupling has been developed under mild conditions. [CpRhCl2]2 was shown to be the most effective catalyst for the transformation. More importantly, good to excellent yields were obtained under room temperature and base-free conditions. This reaction provides a practical, efficient method for the synthesis of aryl- and alkylquinones.

Substituent effects on reactive oxygen species (ROS) generation by hydroquinones

In order to understand the structural aspects of stabilization of hydroquinones and their ability to generate reactive oxygen species (ROS), we designed and synthesized a series of 6-aryl-2,3-dihydro-1,4-benzoquinones. These compounds equilibrate with the corresponding 6-aryl-1,4-dihydroxybenzenes in an organic medium; a linear free energy relationship analysis gave ρ = +2.37, suggesting that this equilibrium was sensitive to electronic effects. The propensity of the compound to enolize appears to determine ROS-generating capability, thus offering scope for tunable ROS generation.

Iron-catalyzed direct C-H arylation of heterocycles and quinones with arylboronic acids

The arylation of C-H bonds to generate heteroaryl-aryl (Het-Ar) and arylated quinone (Quin-Ar) compounds has received great attention to achieve sustainable goals in synthetic chemistry. Despite significant advances, arylation of a broad range of Het-Ar and Quin-Ar derivatives remains a challenging task. Herein, a variety of heterocycles are arylated by using arylboronic acids in the presence of catalytic amounts of inexpensive Fe(NO 3)3. The C-arylated quinone compounds can be prepared by reacting arylboronic acids with either quinone or hydroquinone. The present method is operationally simple, scalable, does not require prefunctionalization of the heterocycle or quinone, and can tolerate a wide variety of functional groups in the coupling partners. These qualities are expected to render this method attractive for academic and industrial use. Direct C-H arylation of a variety of heterocycles and quinones with arylboronic acids has been developed. An inexpensive iron catalyst, Fe(NO3)3, and a co-oxidant, persulfate, were used in air. The protocol is applicable for large-scale synthesis and is expected to find application as a result of its operational simplicity. Copyright

Iron-catalyzed cross-coupling of electron-deficient heterocycles and quinone with organoboron species via innate C-H functionalization: Application in total synthesis of pyrazine alkaloid botryllazine A

Here, we report an iron-catalyzed cross-coupling reaction of electron-deficient heterocycles and quinone with organoboron species via innate C-H functionalization. Iron(II) acetylacetonate along with oxidant (K 2S2O8) and phase-transfer catalyst (TBAB) under open flask conditions efficiently catalyzed the cross-coupling of pyrazine with arylboronic acids and gave monoarylated products in good to excellent yields. Optimized conditions also worked for other heterocylces such as quinoxalines, pyridines, quinoline, and isoquinoline as well as quinones. In addition, we demonstrated as a first example its application for the synthesis of anticancer marine pyrazine alkaloid botryllazine A.

FeSO4-promoted direct arylation of benzoquinones with ArB(OH)2 or ArBF3K

FeSO4·7H2O was proven to work as effective promoter for the direct arylation of benzoquinones with aryl boronic acids in the presence of K2S2O8. In the arylation, slow addition of iron solution was crucial to efficiently proceed with the reaction. Interestingly, the Fe-mediated arylation could be converted into a catalytic reaction by using hydroquinones, instead of benzoquinones, or addition of ascorbic acid.