31603-77-7

Usage

Uses

Used in Chemical Research:
4-Biphenylacetonitrile is used as a research compound for studying the adsorption orientation of biphenyl derivatives on Au colloidal surfaces with α-cyclodextrins. This application is crucial for understanding the interactions between these molecules and the surfaces, which can have implications in various fields, including material science and nanotechnology.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Biphenylacetonitrile is used as an intermediate in the synthesis of various drugs and pharmaceutical compounds. Its unique chemical structure allows for the creation of new molecules with potential therapeutic properties.
Used in Material Science:
4-Biphenylacetonitrile can be utilized in the development of new materials, such as polymers and coatings, due to its ability to form biphenyl derivatives. These derivatives can have specific properties that make them suitable for various applications, including electronics and automotive industries.

InChI:InChI=1/C14H11N/c15-11-10-12-6-8-14(9-7-12)13-4-2-1-3-5-13/h1-9H,10H2

Upstream product

• 2567-29-5 p-phenylbenzyl bromide 
• 143-33-9 sodium cyanide 
• 2942-58-7 diethyl cyanophosphonate 
• 3218-36-8 4-Phenylbenzaldehyde 
• 96824-25-8 Phosphoric acid biphenyl-4-yl-cyano-methyl ester diethyl ester 
• 16532-79-9 4-Bromophenylacetonitrile 
• 98-80-6 phenylboronic acid 
• 151-50-8 potassium cyanide 
• 720-75-2 methyl 4-phenylbenzoate 
• 92-92-2 biphenyl-4-carboxylic acid 
• 1667-11-4 biphenyl-4-methylchloride 
• 32503-27-8 tetra(n-butyl)ammonium hydrogensulfate 
• 67-56-1 methanol 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 101889-77-4 2-bibenzyl-4-yl-pent-4-enenitrile 
• 17027-69-9 2-([1,1'-biphenyl]-4-yl)ethan-1-amine hydrochloride 
• 69808-41-9 2-biphenyl-4-yl-3-morpholin-4-yl-acrylonitrile 
• 17027-51-9 2-(4-biphenyl)ethylamine 
• 94559-54-3 4-(Benzoylamino)-2-(4-biphenylyl)butyronitril 
• 94559-39-4 3-<2-(Benzoylamino)ethyl>-2-(benzoylimino)-3-(4-biphenylyl)pyrrolidin 
• 94559-40-7 2-(Benzoylimino)-3-(4-biphenylyl)pyrrolidin 
• 85809-14-9 4-(Benzoylamino)-2-(4-biphenylyl)-3,3-dimethylbutyronitril 
• 5728-52-9 (4-biphenylyl)acetic acid 
• 176860-59-6 2-([1,1’-biphenyl]-4-yl)-N’-hydroxyacetimidamide 
• 54075-39-7 N'-(2-tert.-Butoxyethyl)-N,N-diphenylharnstoff 
• 122-39-4 diphenylamine 
• 94559-26-9 3-(4-Biphenylyl)-2-oxo-3-pyrrolidincarbonitril 
• 94559-25-8 N,N''-<3-(4-Biphenylyl)-3-cyan-1,5-pentandiyl>bis(N',N'-diphenylharnstoff) 

Relevant academic research and scientific papers

Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes

A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reacti

Assembly of α-(Hetero)aryl Nitriles via Copper-Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides

α-(Hetero)aryl nitriles are important structural motifs for pharmaceutical design. The known methods for direct synthesis of these compounds via coupling with (hetero)aryl halides suffer from narrow reaction scope. Herein, we report that the combination of copper salts and oxalic diamides enables the coupling of a variety of (hetero)aryl halides (Cl, Br) and ethyl cyanoacetate under mild conditions, affording α-(hetero)arylacetonitriles via one-pot decarboxylation. Additionally, the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α-alkyl-substituted ethyl cyanoacetates proceeds smoothly at 60 °C, leading to the formation of α-alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities and heteroaryls.

Biphenyl acetic acid and preparation method thereof

The invention discloses biphenyl acetic acid and a preparation method thereof. The preparation method comprises the following steps: dissolving bromobenzene into dimethylformamide, and performing reaction under the action of palladium powder to obtain biphenyl; dissolving biphenyl in cyclohexane, and performing chloromethylation reaction on biphenyl in a hydrochloric acid solution and a saturatedformaldehyde aqueous solution to obtain an intermediate 1; dissolving sodium cyanide in deionized water, and performing cyanidation reaction on the intermediate 1 and a sodium cyanide aqueous solutionunder the action of a catalyst n-butylammonium bromide to obtain an intermediate 2; and further hydrolyzing the intermediate 2 under the condition of an alkaline aqueous solution, and performing acidifying under the action of hydrochloric acid to obtain biphenyl acetic acid. The yield of the biphenyl acetic acid prepared by the aid of the method is higher than that of the biphenyl acetic acid prepared by the aid of traditional processes, reactants are low in price, the preparation cost of the biphenyl acetic acid can be greatly reduced, and the method is favorable for market popularization.

Cu(OAc)2 entrapped on ethylene glycol-modified melamine–formaldehyde polymer as an efficient heterogeneous catalyst for Suzuki–Miyaura coupling reactions

This work is described as an environmental friendly approach for Cu(OAc)2 entrapped on ethylene glycol-modified melamine–formaldehyde-based polymeric material (Cu@MCOP) which has been successfully synthesized by simple approaches using commercially available starting materials via solvothermal techniques and without using any toxic reagents and chemicals. The structural, morphological, physicochemical characteristics and catalytic activity of the heterogeneous catalyst (Cu@MCOP) were analyzed by various instrumental methods including powder X-ray diffraction, FT-IR, UV-DRS, X-ray photoelectron spectroscopy, SEM and elemental mapping which have been used to authenticate the polymeric materials Cu@MCOP. The catalytic performance of Cu@MCOP as solid heterogeneous catalyst was evaluated in synthesis of various biphenyl derivatives through Suzuki–Miyaura cross-coupling reactions of various aryl halides with substituted organoboranes under normal reaction conditions. Furthermore, the copper catalyst was easily available, low cost, cheap and best instead of palladium, which shows good catalytic activity and excellent yield (up to 86%); the catalyst can be separated easily and recycled for more than five times. Graphic abstract: [Figure not available: see fulltext.].

Design of biphenyl-substituted diarylpyrimidines with a cyanomethyl linker as HIV-1 NNRTIs via a molecular hybridization strategy

The key problems of human immunodeficiency virus (HIV) therapy are the rapid emergence of drug-resistant mutant strains and significant cumulative drug toxicities. Therefore, there is an urgent demand for new anti-HIV agents with low toxicity and broad-spectrum antiviral potency. A series of biphenyl-substituted diarylpyrimidines with a cyanomethyl linker were designed using a molecular hybridization strategy. The cell-based anti-HIV assay showed that most of the compounds exhibited moderate to good activities against wild-type HIV-1 and clinically relevant mutant strains with a more favorable toxicity, and the enzymatic assay showed they had nanomolar activity against reverse transcriptase (RT). Compound 10p exhibited the best activity against wild-type HIV-1 with an EC50 (50% HIV-1 replication inhibitory concentration) value of 0.027 μM, an acceptable CC50 (50% cytotoxic concentration) value of 36.4 μM, and selectivity index of 1361, with moderate activities against the single mutants (EC50: E138K, 0.17 μM; Y181C, 0.87 μM; K103N, 0.9 μM; L100I, 1.21 μM, respectively), and an IC50 value of 0.059 μM against the RT enzyme, which was six-fold higher than nevirapine (NVP). The preliminary structure–activity relationship (SAR) of these new compounds was concluded. The molecular modeling predicted the binding modes of the new compounds with RT, providing molecular insight for further drug design.

Hydroximoyl fluorides as the precursors of nitrile oxides: Synthesis, stability and [3 + 2]-cycloaddition with alkynes

The transformation of hydroximoyl fluorides to nitrile oxides for [3 + 2]-cycloaddition with alkynes has been achieved for the first time. The hydroximoyl fluorides used in this work appeared to be not stable, which was proved by a series of experiments. A DFT calculation was performed to better understand the properties of hydroximoyl fluorides. Although not stable, the hydroximoyl fluorides could be successfully converted to the corresponding nitrile oxides for in situ [3 + 2]-cycloaddition with alkynes to yield the isoxazoles. Furthermore, it was feasible to conduct [3 + 2]-cycloaddition reaction without purification after the synthesis of hydroximoyl fluorides from gem-difluoroalkenes. By investigating a class of interesting yet previously rarely explored fluorinated compounds, this work sheds new light on the stability and reactivity of a C-F bond on a CN double bond.

Ligand-Free Bioinspired Suzuki–Miyaura Coupling Reactions using Aryltrifluoroborates as Effective Partners in Deep Eutectic Solvents

Pd-catalyzed Suzuki–Miyaura cross-coupling between (hetero)aryl halides (Cl, Br, I) and versatile, moisture-stable mono- and bifunctional potassium aryltrifluoroborates proceeded efficiently and chemoselectively in air and under generally mild conditions; a catalyst loading as low as 1 mol % combined with Na2CO3 as a base in choline chloride/glycerol (1:2) deep eutectic solvent (DES) was used as a sustainable and environmentally responsible medium. The catalyst, base, and DES were easily and successfully recycled up to six times with an E-factor as low as 8.74. Valuable biaryls and terphenyl derivatives were furnished in yields of up to 98 %; over 50 reactions were compared and discussed. The methodology was applied for the synthesis of the nonsteroidal anti-inflammatory drugs Felbinac and Diflunisal.

One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions

A one-pot protocol to obtain C1-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting methyl vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with molecular iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alcohol into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method.

Preparation and purification methods of 4-biphenylacetic acid

The invention relates to the field of production preparation of compounds, in particular to preparation and purification methods of 4-biphenylacetic acid. The preparation and purification methods comprise steps as follows: 1) biphenyl is subjected to a chloromethylation reaction to produce 4-phenyl benzyl chloride; 2) 4-phenyl benzyl chloride reacts with sodium cyanide to produce 4-biphenyl acetonitrile; 3) 4-biphenyl acetonitrile is hydrolyzed and a crude 4-bphenylacetic acid product is obtained; 4) the crude 4-bphenylacetic acid product and methanol are subjected to an esterification reaction to produce 4-biphenyl methyl acetate, 4-biphenyl methyl acetate is purified and hydrolyzed into 4-biohenylacetic acid, 4-bihenylacetic acid is refined, and a finished product is prepared.

Hydride Reduction by a Sodium Hydride-Iodide Composite

Sodium hydride (NaH) is widely used as a Br?nsted base in chemical synthesis and reacts with various Br?nsted acids, whereas it rarely behaves as a reducing reagent through delivery of the hydride to polar π electrophiles. This study presents a series of reduction reactions of nitriles, amides, and imines as enabled by NaH in the presence of LiI or NaI. This remarkably simple protocol endows NaH with unprecedented and unique hydride-donor chemical reactivity.