216017-01-5

Usage

Uses

Used in Scientific Research:
1,1'-Biphenyl, 4-methyl-4'-(phenylmethyl)is used as a fluorescence probe for the detection and analysis of proteins, lipids, and nucleic acids in biological and environmental research. Its fluorescent properties allow for the monitoring and study of these biomolecules, contributing to a better understanding of their structure and function.
Used in Industrial Production:
In the industrial sector, 1,1'-Biphenyl, 4-methyl-4'-(phenylmethyl)is utilized in the production of dyes, pharmaceuticals, and organic intermediates. Its versatility and solubility in organic solvents make it a suitable compound for the synthesis of various products, enhancing the efficiency and effectiveness of manufacturing processes.

Upstream product

• 93718-73-1 4-benzylphenyl methanesulfonate 
• 5720-05-8 4-methylphenylboronic acid 
• 1160484-32-1 4-benzylphenyl tosylate 
• 100-59-4 phenylmagnesium chloride 
• 79757-92-9 (4'-methyl-[1,1'-biphenyl]-4-yl)methanol 
• 589-17-3 p-bromobenzyl chloride 
• 38580-84-6 4'-methyl-1,1'-biphenyl-4-yl-methylchloride 
• 98-80-6 phenylboronic acid 
• 90252-89-4 p-tolylzinc(II) chloride 
• 957847-58-4 C₅₇H₅₂O₁₂S₄ 
• 1589-82-8 phenylmagnesium bromide 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 834-14-0 p-benzylanizole 
• 101-53-1 p-benzylphenol 

Relevant academic research and scientific papers

Pd-catalyzed, highly selective C(sp2)-Br bond coupling reactions of o-(or m-, or p-) chloromethyl bromobenzene with arylboronic acids

Highly selective C(sp2)–C(sp2) cross-coupling of dihalogenated hydrocarbons comprising C(sp2)–Br and C(sp3)–Cl bonds with arylboronic acids is reported. This highly selective coupling reaction of the C(sp2)–Br bond is successfully achieved using Pd(OAc)2 and PCy3·HBF4 as the palladium source and ligand, respectively. A series of chloromethyl-1,1′-biphenyl compounds are obtained in moderate-to-excellent yields. Moreover, this protocol can be extended to the one-pot dual arylation of 1-bromo-4-(chloromethyl)benzene with two arylboronic acids, leading to diverse unsymmetrical 4-benzyl-1,1′-biphenyl derivatives.

Pincer-Nickel-Catalyzed Cross-Coupling of Aryl Sulfamates with Arylzinc Chlorides

The nickel N,N,N-pincer complex 2 was demonstrated to effectively catalyze the cross-coupling of aryl sulfamates with arylzinc chlorides under mild conditions. The reaction is suitable for a wide range of substrates, and tolerates various functional groups. A nickel N,N,N-pincer complex effectively catalyzes the cross-coupling of aryl sulfamates with arylzinc chlorides under mild conditions. The reaction is suitable for a wide range of substrates, and tolerates various functional groups.

Parallel and combinatorial liquid-phase synthesis of alkylbiphenyls using pentaerythritol support

Unfunctionalized alkylbiphenyls were fabricated by a parallel and combinatorial synthesis using pentaerythritol as a tetrapodal soluble support for a sulfonate-based traceless multifunctional linker system. Nickel N-heterocyclic carbene-catalyzed reactions of pentaerythritol tetrakis(biphenylsulfonate)s with primary alkylmagnesium bromides generated the alkylbiphenyl derivatives by desulfitative cleavage/cross-coupling of the C-S bond without any memory of the attachment on the support. Though the reactions were completed with sufficient yields in 12 h at room temperature, even with only 1.5 equiv of nucleophiles, they still retained the benefits of facile isolation observed in polymer-supported reactions.

Direct arylation/alkylation/magnesiation of benzyl alcohols in the presence of grignard reagents via Ni-, Fe-, or Co-catalyzed sp3 C-O Bond activation

Direct application of benzyl alcohols (or their magnesium salts) as electrophiles in various reactions with Grignard reagents has been developed via transition metal-catalyzed sp3 C-O bond activation. Ni complex was found to be an efficient catalyst for the first direct cross coupling of benzyl alcohols with aryl/alkyl Grignard reagents, while Fe, Co, or Ni catalysts could promote the unprecedented conversion of benzyl alcohols to benzyl Grignard reagents in the presence of nhexylMgCl. These methods offer straightforward pathways to transform benzyl alcohols into a variety of functionalities.

Kumada-Tamao-Corriu coupling of heteroaromatic chlorides and aryl ethers catalyzed by (IPr)Ni(allyl)Cl

The complex (IPr)Ni(allyl)Cl (IPr = 1,3-bis(2,6-diisopropylphenyl) imidazolidene) catalyzes the cross-coupling reactions of heteroaromatic chlorides with aryl Grignard reagents. Catalyst loadings as low as 0.1 mol % have been used to afford the products in excellent yields. This nickel-based catalytic system also promotes the activation of the CAr-O bond of anisoles in the Kumada-Tamao-Corriu reaction under fairly mild conditions.

Cross-coupling of aryl/alkenyl ethers with aryl grignard reagents through nickel-catalyzed C-O activation

The formation of a C-C bond has been achieved through the cleavage of the sp2 C-O bond of aryl/alkenyl ethers catalyzed by a nickel complex, and by using Grignard reagents as nucleophiles (see scheme). This method displays a broad substrate scope and leads to good to excellent yields of the aryl-aryl or alkenyl-aryl cross-coupling products.

Rhodium/N-heterocyclic carbene-catalyzed cross-couplings of aryl arenesulfonates with arylboronic acids

The combination of rhodium(I) and N-hetercyclic carbenes (NHC) was found to be effective as a catalyst for cross-coupling reactions of aryl arenesulfonates with arylboronic acids, which gave rise to the desired biaryl compounds in good yields.

Synthesis of biaryls via nickel-catalyzed cross-coupling reaction of arylboronic acids and aryl mesylates

The cross-coupling reaction of arylboronic acids (1.3 equivs) with aryl methanesulfonates was carried out in the presence of a nickel(0) catalyst (3 mol%) and K3PO4·nH2O (3 equivs). The use of toluene as the solvent and the nickel(0)-dppf catalyst prepared from NiCl2(dppf) plus dppf with BuLi were recognized to be the most efficient to achieve both high yields and high selectivity. The reaction can be applied to various electron-deficient and - rich aryl methanesulfonates to give high yields.