93504-10-0

Usage

Purity

97%

Classification

Organic compound

Molecular weight

160.17 g/mol

Usage

Reagent in organic synthesis, precursor in the production of dyes and pharmaceuticals

Properties

Antioxidant

Potential applications

Medicine, photodynamic therapy, energy storage devices

Upstream product

• 63815-25-8 3-methylbenzene diazonium 
• 106-51-4 p-benzoquinone 
• 1422-76-0 3-methylbenzenediazonium tetrafluoroborate 
• 123-31-9 hydroquinone 
• 108-44-1 1-amino-3-methylbenzene 
• 17933-03-8 m-tolylboronic acid 
• 625-95-6 3-Iodotoluene 
• 108-88-3 toluene 
• 1416276-98-6 bis(3-methylphenyl)iodonium trifluoromethanesulfonate 

Downstream Products

• 327078-56-8 5-hydroxy-7-(3-methylphenyl)benzo[1,3]oxathiol-2-one 

Relevant academic research and scientific papers

Mn-Catalyzed 1,6-conjugate addition/aromatization of: Para -quinone methides

A series of ferrocenyl triazole ligands have been synthesized and characterized, which proved to be effective for the Mn-catalyzed 1,6-conjugate addition/aromatization of para-quinone methides with good to high yields under mild conditions. This protocol provided an efficient and practical route to the synthetically interesting functionalized quinones, methines and their analogues.

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.

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.

Palladium-catalyzed direct C-H functionalization of benzoquinone

A direct Pd-catalyzed C-H functionalization of benzoquinone (BQ) can be controlled to give either mono- or disubstituted BQ, including the installation of two different groups in a one-pot procedure. BQ can now be directly functionalized with aryl, heteroaryl, cycloalkyl, and cyclo-alkene groups and, moreover, the reaction is conducted in environmentally benign water or acetone as solvents.

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.

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.

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

The direct arylation of benzoquinones with arylboronic acid promoted by iron(II) oxalate

Arylations of various quinones with several arylboronic acids have been developed. The reactions proceed readily at ambient temperature using iron(II) oxalate as a catalyst and potassium persulfate as a co-oxidant. The mechanism is presumed to proceed through a nucleophilic radical addition to the quinone with in situ reoxidation of the resulting dihydroquinone.

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.

Iron-mediated direct arylation with arylboronic acids through an aryl radical transfer pathway

A novel iron-mediated direct C-H arylation of quinones and pyridine analogues with arylboronic acids has been developed using dichloromethane and water as solvents at ambient temperature. FeS is employed and serves as an efficient catalyst. A detailed reaction mechanism is speculated and expounded.