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Usage

Uses

Used in Pharmaceutical Industry:
[1,1'-BIPHENYL]-2-CARBOXALDEHYDE,4-METHOXYis used as a building block in organic synthesis for the development of various pharmaceuticals. Its unique structure allows for the creation of a wide range of medicinal compounds, contributing to the advancement of drug discovery and therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, [1,1'-BIPHENYL]-2-CARBOXALDEHYDE,4-METHOXYserves as a starting material for the production of different agrochemicals. Its role in this sector is crucial for the development of innovative products that can enhance crop protection and improve agricultural practices.
Used in Functional Materials:
[1,1'-BIPHENYL]-2-CARBOXALDEHYDE,4-METHOXYis utilized in the synthesis of functional materials, which are essential in various technological applications. These materials often possess unique properties, such as conductivity, magnetism, or optical activity, making them valuable in the development of advanced devices and systems.
Used in Dyes and Pigments Production:
[1,1'-BIPHENYL]-2-CARBOXALDEHYDE,4-METHOXYis also known for its use in the production of dyes and pigments. Its chemical structure allows for the creation of a diverse array of colorants that can be applied in various industries, including textiles, plastics, and printing inks.
Used as a Flavoring Agent in the Food Industry:
[1,1'-BIPHENYL]-2-CARBOXALDEHYDE,4-METHOXYis employed as a flavoring agent in the food industry, where it contributes to the enhancement of taste and aroma in various products. Its use in this sector highlights its versatility and the broad range of applications it offers.

Upstream product

• 7507-86-0 2-bromo-5-methoxy-benzaldehyde 
• 98-80-6 phenylboronic acid 
• 603-33-8 triphenylbismuthane 
• 100-58-3 phenylmagnesium bromide 
• 637-59-2 1-Bromo-3-phenylpropane 
• 108-86-1 bromobenzene 
• 93-02-7 2,5-dimethoxybenzaldehyde 

Downstream Products

• 1292302-49-8 2-methoxy-9-[(4-methylphenyl)sulfonylamino]fluorene 
• 1304460-98-7 C₂₁H₁₉NO₃S 
• 42523-32-0 8-methoxy-6H-dibenzo[b,d]pyran-6-one 

Relevant academic research and scientific papers

Catalytic Cleavage of Unactivated C(aryl)-P Bonds by Chromium

We describe here the coupling to transform aryl phosphine derivatives by the cleavage of unactivated C(aryl)-P bonds with chromium catalysis, allowing us to achieve the reaction with alkyl bromides and arylmagnesium reagents under mild conditions. Mechani

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible N-methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous functional groups (methoxy, cyano, nitro, chloro, and SEM and TBS-protective groups for phenols) and was further utilized in the first total synthesis of the natural product nobilone.

Metal-Free Electrochemical Coupling of Vinyl Azides: Synthesis of Phenanthridines and β-Ketosulfones

We reported an efficient and environmentally benign electrochemical synthesis of phenanthridines by oxidative coupling of vinyl azides with sodium azide or benzenesulfonyl hydrazides, for the first time. The reaction conditions are mild, and no additional metal-catalyst or exogenous oxidants are needed. The protocol has broad substrate scope and high functional group tolerance. Furthermore, this green electrochemical procedure can be readily extended to the synthesis of β-ketosulfones. Gram scale reactions further demonstrate the practicability.

Low-Valent, High-Spin Chromium-Catalyzed Cleavage of Aromatic Carbon-Nitrogen Bonds at Room Temperature: A Combined Experimental and Theoretical Study

The cleavage of aromatic carbon-nitrogen bonds catalyzed by transition metals is of high synthetic interest because such bonds are common in organic chemistry. However, few metal catalysts can be used to selectively break C(aryl)-N bonds in electronically neutral molecules. We report here the first low-valent, high-spin chromium-catalyzed cleavage of C(aryl)-N bonds in electronically neutral aniline derivatives at room temperature. By using simple and inexpensive chromium(II) chloride as precatalyst, accompanied by an imino auxiliary, the selective arylative and alkylative C-C coupling of C(aryl)-N bonds can be achieved. Crossover experiments indicate that a low-valent chromium species, formed in situ by reduction of CrCl2 with Grignard reagent, is responsible for the catalytic cleavage of C(aryl)-N bonds. DFT calculations show that facile insertion of the C(aryl)-N bond by chromium(0) can take place in a high-spin quintet (S = 2) ground state, whereas the lower-spin singlet (S = 0) and triplet (S = 1) states are inaccessible in energy. It was found that both donation of the sole paired d electrons in the d6 shell of high-spin chromium(0) to the antibonding orbital of the C(aryl)-N bond and the nitrogen ligating interaction to the metal center with its lone pair play important roles in the cleavage of the C(aryl)-N bond by the zerovalent chromium species.

Chromium-Catalyzed, Regioselective Cross-Coupling of C-O Bonds by Using Organic Bromides as Reactants

We report a chromium-catalyzed cross-coupling of C-O bonds with widely accessible organic bromides as reactants for the preparation of ortho -arylated or -alkylated aromatic aldehydes at room temperature. The use of metallic magnesium is essential for the reaction to occur, giving it an advantage over previous reactions involving Grignard reagents that have to be prepared separately from organic halides before the coupling.

Synthesis of dibenzopyranones and pyrazolobenzopyranones through copper(0)/Selectfluor system-catalyzed double C[sbnd]H activation/oxygen insertion of 2-arylbenzaldehydes and 5-arylpyrazole-4-carbaldehydes

A mild and efficient protocol for the synthesis of dibenzopyranones and pyrazolobenzopyranones was developed involving a copper(0)/Selectfluor system-catalyzed double C[sbnd]H activation/oxygen insertion of 2-arylbenzaldehydes and 5-arylpyrazole-4-carbaldehydes. Preliminary mechanistic studies suggest that both water and dioxygen act as the oxygen source in the formation of pyranone scaffolds.

UV light-mediated difunctionalization of alkenes with CF3SO2Na: Synthesis of trifluoromethyl phenanthrene and anthrone derivatives

A metal-free and cost-effective protocol for UV light-mediated difunctionalization of alkenes with CF3SO2Na was developed. This strategy realized the direct formation of Csp3-CF3 and C-C bonds through a proposed

Regio- and Chemoselective Kumada-Tamao-Corriu Reaction of Aryl Alkyl Ethers Catalyzed by Chromium under Mild Conditions

Acting as an environmentally benign synthetic tool, the cross-coupling reactions with aryl ethers via C-O bond activation have attracted broad interest. However, the functionalizations of C-O bonds are mainly limited to nickel catalysis, and selectivity has long been a prominent challenge when several C-O bonds are present in the one molecule. We report here the first chromium-catalyzed selective cross-coupling reactions of aryl ethers with Grignard reagents by the cleavage of C-O(alkyl) bonds. Diverse transformations were achieved using simple, inexpensive chromium(II) precatalyst combining imino auxiliary at room temperature. It offers a new avenue for buildup functionalized aromatic aldehydes with high efficiency and selectivity.

Enantioselective palladium-catalyzed dearomative cyclization for the efficient synthesis of terpenes and steroids

A novel enantioselective palladium-catalyzed dearomative cyclization has been developed for the efficient construction of a series of chiral phenanthrenone derivatives bearing an all-carbon quaternary center. The effectiveness of this method in the synthe

Copper catalyzed room temperature lactonization of aromatic C-H bond: A novel and efficient approach for the synthesis of dibenzopyranones

We have developed a novel and efficient methodology for the intramolecular aryl C-H oxidative lactonization of 2-arylbenzaldehyde using a low-cost CuCl catalyst and TBHP as the oxidant at room temperature. We applied the methodology to the synthesis of a series of dibenzopyranones.