20114-55-0

Usage

Uses

Used in Chemical Research and Synthesis:
BMH is used as a reagent for the determination and detection of various metal ions in solution, thanks to its ability to form complexes with metal ions.
Used in Pharmaceutical and Biological Applications:
BMH is used as an antioxidant and antimicrobial agent, making it potentially useful in pharmaceutical and biological applications.

Upstream product

• 958-80-5 bis(4-methoxyphenyl)thione 
• 90-96-0 bis(p-methoxyphenyl)methanone 

Downstream Products

• 2186-95-0 4,4′-dimethoxybenzhydryl methyl ether 
• 726-18-1 4,4'-dianisylmethane 
• 2186-93-8 4,4’-dimethoxybenzophenone dimethyl acetal 
• 35525-34-9 Methyl 1-methyl-2,2-bis(4-methoxyphenyl)cyclopropanecarboxylate 
• 5831-42-5 4,4'-dimethoxybenzophenone azine 
• 1221-72-3 Bis(p-methoxyphenyl)diazomethan 
• 92806-47-8 4,4'-dimethoxybenzophenone (diphenylacetyl)hydrazone 
• 1441324-00-0 4,4’-(((1,1,1,3,3,3-hexafluoropropan-2-yl)oxy)methylene)bis(methoxybenzene) 
• 1627149-43-2 3,4-bis(4-chlorophenyl)-6-methoxy-1-(4-methoxyphenyl)isoquinoline 

Relevant academic research and scientific papers

Photochemical Carbene Transfer Reactions of Aryl/Aryl Diazoalkanes—Experiment and Theory**

Controlling the reactivity of carbene intermediates is a key parameter in the development of selective carbene transfer reactions and is usually achieved by metal complexes via singlet metal-carbene intermediates. In this combined experimental and computational studies, we show that the reactivity of free diaryl carbenes can be controlled by the electronic properties of the substituents without the need of external additives. The introduction of electron-donating and -withdrawing groups results in a significant perturbation of singlet triplet energy splitting of the diaryl carbene intermediate and of activation energies of consecutive carbene transfer reactions. This strategy now overcomes a long-standing paradigm in the reactivity of diaryl carbenes and allows the realization of highly chemoselective carbene transfer reactions with alkynes. We could show that free diaryl carbenes can be readily accessed via photolysis of the corresponding diazo compounds and that these carbenes can undergo highly chemoselective cyclopropenation, cascade, or C?H functionalization reactions. Experimental and theoretical mechanistic analyses confirm the participation of different carbene spin states and rationalize for the observed reactivity.

Copper-Mediated Cross-Coupling of Diazo Compounds with Sulfinates

A copper-mediated cross-coupling reaction between a diazo compound and a sodium alkane(arene)sulfinate gives a sulfone as the product. This reaction proceeds under mild conditions and features excellent functional group compatibility. A wide range of sodium alkane(arene)sulfinates were successfully applied in this chemistry. Mechanistic studies revealed that the overall reaction efficiency of the sulfinates was in line with their nucleophilicity in this reaction.

Silver-Catalyzed N-H Functionalization of Aryl/Aryl Diazoalkanes with Anilines

Herein, we report on the N-H functionalization reaction of primary and secondary anilines with diaryldiazoalkanes using simple AgPF6 as catalyst. We demonstrated broad applicability in the reaction of diaryldiazoalkanes with different anilines (31 examples, up to 97% yield). Furthermore, we propose a possible reaction mechanism for the N-H functionalization.

Experimental and Computational Studies on Stepwise [3+2]-Cycloadditions of Diaryldiazomethanes with Electron-Deficient Dimethyl (E)- and (Z)-2,3-Dicyanobutenedioates

Electron-deficient dimethyl (E)- and (Z)-2,3-dicyanobutenedioates (dimethyl dicyanofumarate and dicyanomaleate, respectively) react with diaryldiazomethanes at room temperature under spontaneous evolution of N2. The type of the products strongly depends on the structure of the diazo compound. Whereas diphenyldiazomethane and its bis(4-methoxy) derivative yield cyclopropanes, sterically crowded 5-diazo-5H-dibenzo[a,d]cycloheptane derivatives afford either the dimer of the carbene formed via N2 elimination or the adduct of the carbene onto the starting diazo compound. The course of the studied reactions is rationalized by stepwise mechanisms initiated by the formation of a C–N bond. A cascade of reactions leads to the corresponding cyclopropanes or to release of a carbene species. The formation of a pyrazole via [3+2]-cycloaddition (32CA) is observed only in reactions with (trimethylsilyl)diazomethane, which behaves similar to the parent diazomethane. The proposed mechanisms were analyzed computationally using the DFT method.

Efficient synthesis of ferrocifens and other ferrocenyl-substituted ethylenes: Via a 'sulfur approach'

Stable and non-odorous alkyl ferrocenyl thioketones react with bis(4-methoxyphenyl)diazomethane according to the 'two-fold extrusion' reaction principles, and tetrasubstituted ethylenes obtained thereby can be demethylated to give (Fc,2OH)-ferrocifens in good yields. The method offers an alternative approach to this class of medically relevant compounds. A similar protocol with alkyl ferrocenyl thioketones and selected diaryldiazomethanes leads to ferrocenyl-substituted ethylenes including dibenzofulvenes. These products are of potential interest for electrochemical and photophysical studies.

Microwave assisted solvent-free C-H amination by silica-supported manganese dioxide

An effective and convenient method has been developed for the preparation of 1-unsubstituted 1H-indazoles via C-H amination of N-acetylhydrazones in the presence of a catalytic amount of manganese dioxide under microwave irradiation. This new method featured easy operation and relatively short reaction-time.

Facile Synthesis of Isoindolinones via Rh(III)-Catalyzed One-Pot Reaction of Benzamides, Ketones, and Hydrazines

A Rh(III)-catalyzed one-pot reaction of benzamides, ketones, and hydrazines for facile access to isoindolinones is reported. In this method, various ketones are transformed into donor-donor diazo compounds, which sequentially engage in insertion with benzamides under Rh(III) catalysis to generate N-substituted quaternary isoindolinones. (Chemical Presented).

Cu(I)-catalyzed coupling of diaryldiazomethanes with terminal alkynes: An efficient synthesis of tri-aryl-substituted allenes

A highly efficient method for the synthesis of tri-aryl-substituted allenes has been developed through Cu(I)-catalyzed coupling of diaryldiazomethanes with terminal alkynes. The reaction is under mild conditions and uses simple and inexpensive CuI as the catalyst. Mechanistically, the reaction follows a pathway involving Cu(I) carbene migratory insertion.

Cross-Coupling between Difluorocarbene and Carbene-Derived Intermediates Generated from Diazocompounds for the Synthesis of gem-Difluoroolefins

Cross-coupling between difluorocarbene and carbene-derived intermediates generated from diazocompounds was developed to give gem-difluoroolefins, which constitutes a fast practical pathway to achieve hindered gem-difluoroolefins. The cross-coupling between difluorocarbene and aryl diazoacetates proceeded smoothly in the presence of a copper source, whereas its coupling with diaryl diazomethanes occurred well under metal-free conditions. A mechanism involving a copper-difluorocarbene complex was proposed.

The First Crystal Structure of a Reactive Dirhodium Carbene Complex and a Versatile Method for the Preparation of Gold Carbenes by Rhodium-to-Gold Transmetalation

The dirhodium carbene derived from bis(4-methoxyphenyl)diazomethane and [Rh(tpa)4]·CH2Cl2 (tpa=triphenylacetate) was characterized by UV, IR, and NMR spectroscopy, HRMS, as well as by X-ray diffraction. The isolated comple