4578-79-4

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
(4-methoxyphenyl)(phenyl)acetonitrile is used as a key intermediate in the synthesis of various pharmaceutical and agrochemical compounds. Its chemical reactivity allows for the creation of a wide range of products with different therapeutic and pesticidal properties.
Used in Organic Synthesis:
As a building block in organic synthesis, (4-methoxyphenyl)(phenyl)acetonitrile is utilized for its capacity to undergo multiple chemical reactions, making it a valuable component in the development of complex organic molecules.
Used in Dye and Pigment Production:
(4-methoxyphenyl)(phenyl)acetonitrile also serves as a precursor in the production of dyes, pigments, and other specialty chemicals, contributing to the coloration and properties of these products.
Safety Considerations:
It is crucial to handle (4-methoxyphenyl)(phenyl)acetonitrile with care due to its potential harmful effects if ingested or inhaled, and its ability to cause skin and eye irritation. Proper safety measures should be taken during its use and storage to minimize risks.

Upstream product

• 5798-79-8 bromo-phenyl-acetonitrile 
• 100-66-3 methoxybenzene 
• 7677-24-9 trimethylsilyl cyanide 
• 834-14-0 p-benzylanizole 
• 6731-11-9 4-methoxybenzhydryl chloride 
• 143-33-9 sodium cyanide 
• 151-50-8 potassium cyanide 
• 720-44-5 1-(4-methoxyphenyl)-1-phenylmethanol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 140-29-4 phenylacetonitrile 
• 102-96-5 (2-nitroethenyl)benzene 
• 100-09-4 4-methoxybenzoic acid 
• 100-07-2 4-methoxy-benzoyl chloride 
• 3899-91-0 4-methoxyphenyl p-toluenesulfonate 

Downstream Products

• 104357-17-7 (2S,4S)-4-Dimethylamino-2-(p-methoxyphenyl)-2-phenylpentanenitrile 
• 104357-17-7 (2R,4S)-4-Dimethylamino-2-(p-methoxyphenyl)-3-methyl-2-phenylbutanenitrile 
• 611-94-9 4-Methoxybenzophenone 
• 104357-17-7 4-Dimethylamino-2-(p-methoxyphenyl)-2-phenylpentanenitrile 
• 137032-20-3 4-Dimethylamino-2-(p-methoxyphenyl)-3-methyl-2-phenylbutanenitrile 
• 14819-41-1 2-(4-methoxy-phenyl)-2-phenyl-thioacetamide 
• 51431-54-0 2-(p-methoxyphenyl)-2-phenylethylamine 
• 21749-83-7 α-(4-methoxyphenyl)phenylacetic acid 
• 1646856-87-2 2-(4-methoxyphenyl)-2-phenylpent-4-enenitrile 

Relevant academic research and scientific papers

Hypervalent Iodonium Alkynyl Triflate Generated Phenylcyanocarbene and Its Reactivity with Aromatic Systems

Phenylcyanocarbene was generated by the reaction of azide with a hypervalent iodonium alkynyl triflate and reacted in situ with 21 different carbocyclic and heterocyclic aromatic compounds. These reactions led to more complex products that frequently underwent subsequent rearrangements. The reactivity was further explored in a mechanistic study to ascertain the chemoselectivity and stereospecificity.

Structure-Based Design of High-Affinity Fluorescent Probes for the Neuropeptide Y Y1Receptor

The recent crystallization of the neuropeptide Y Y1 receptor (Y1R) in complex with the argininamide-type Y1R selective antagonist UR-MK299 (2) opened up a new approach toward structure-based design of nonpeptidic Y1R ligands. We designed novel fluorescent probes showing excellent Y1R selectivity and, in contrast to previously described fluorescent Y1R ligands, considerably higher (～100-fold) binding affinity. This was achieved through the attachment of different fluorescent dyes to the diphenylacetyl moiety in 2 via an amine-functionalized linker. The fluorescent ligands exhibited picomolar Y1R binding affinities (pKi values of 9.36-9.95) and proved to be Y1R antagonists, as validated in a Fura-2 calcium assay. The versatile applicability of the probes as tool compounds was demonstrated by flow cytometry- and fluorescence anisotropy-based Y1R binding studies (saturation and competition binding and association and dissociation kinetics) as well as by widefield and total internal reflection fluorescence (TIRF) microscopy of live tumor cells, revealing that fluorescence was mainly localized at the plasma membrane.

Synthesis of Chiral Triarylmethanes Bearing All-Carbon Quaternary Stereocenters: Catalytic Asymmetric Oxidative Cross-Coupling of 2,2-Diarylacetonitriles and (Hetero)arenes

A direct and enantioselective oxidative cross-coupling of racemic 2,2-diarylacetonitriles with electron-rich (hetero)arenes has been described, which allows for efficient construction of triarylmethanes bearing all-carbon quaternary stereocenters with excellent chemo- and enantioselectivity. The reaction has an excellent functional group tolerance, and exhibits a broad scope with respect to both 2,2-diarylacetonitrile and (hetero)arene components. The rich chemistry of the cyano group allows for facile synthesis of other valuable chiral triarylmethanes bearing all-carbon quaternary centers that are otherwise difficult to access.

Palladium-Catalyzed Direct α-Arylation of Arylacetonitriles with Aryl Tosylates and Mesylates

The first general palladium-catalyzed α-arylation of arylacetonitriles with aryl and heteroaryl sulfonates are reported. Pd(OAc)2 associated with XPhos serves as the effective catalyst to facilitate this reaction. A broad range of electron-rich, -neutral, -deficient, and sterically hindered aryl/heteroaryl tosylates and mesylates are coupled with arylacetonitriles bearing different substituents to give the corresponding products in good to excellent yields. Catalyst loading down to 0.1 mol-% Pd was achieved, and 22 unprecedented compounds were synthesized from 43 demonstrated examples using this method. Its applicability with the modification of biological phenolic compounds was successfully demonstrated. The Pd/XPhos system catalyzed the α-arylation and followed by alkylation in one-pot sequential conditions, resulting in the direct synthesis of compounds containing quaternary center- and deuterium-containing compounds in good to excellent yields.

Scalable α-Arylation of Nitriles in Aqueous Micelles using Ultrasmall Pd Nanoparticles: Surprising Formation of Carbanions in Water

A scalable synthetic method is described for both the preparation of ultrasmall palladium nanoparticles and their subsequent use in catalyzing an α-arylation reaction of nitriles in aqueous micelles. This method involves the intermediacy of carbanions or keteniminates, which are presumably stabilized by the micellar environment rather than being quenched with water. These Pd nanoparticles are thoroughly characterized. Mechanistic studies using 31P NMR spectroscopy revealed the binding of phosphine ligand with the Pd surface and control experiment confirmed the zero-oxidation state of palladium. The scope of the transformation is demonstrated over 35 examples, including one at 50 g scale.

2-ETHYLIDENE-1,5-DIMETHYL-3,3-DIPHENYLPYRROLIDINE ANALOGS AND METHODS FOR THEIR SYNTHESIS AND USE

The present invention relates to novel 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine analogs, and methods for their synthesis and use. Such analogs are designed to provide a convenient linkage chemistry for coupling under mild conditions to a suitable group on a target protein, polypeptide, solid phase or detectable label.

BF3·OEt2-mediated [1,2]-aryl shift: Synthesis of functionalized α-arylnitriles via the bromination/cyanation/deformylation of substituted deoxybenzoin

A new sequential, tandem synthesis of functionalized α-arylnitriles via the bromination/cyanation/deformylation of substituted deoxybenzoin has developed. CuBr2-promoted bromination of substituted deoxybenzoins gives 2-bromo-2-arylacetophenne 3. The cyanation of 3 with sodium cyanide (NaCN) generates epoxynitrile. Then, a treatment of epoxynitrile with BF3·OEt2 results in the formation of functionalized α-arylnitriles 4 via a 1,2-aryl shift.

Palladium-Catalyzed Regiodivergent Substitution of Propargylic Carbonates

The palladium(0)-catalyzed, ligand-controlled, regioselective addition of diaryl acetonitrile pronucleophiles to propargylic carbonates is reported. Selective formation of either terminal 1,3-dienyl or propargylated products is proposed to arise from a change in reaction mechanism controlled by the denticity of the coordinating ligand.

Nitroalkenes as surrogates for cyanomethylium species in a one-pot synthesis of non-symmetric diarylacetonitriles

Nitroalkenes were used as synthetic equivalents of the cyanomethylium cation in a modular, one-pot synthesis of 2-(3-indolyl)acetonitriles and 2,2-diarylacetonitriles involving electrophilic functionalization of aromatic and heteroaromatic C-H bond.

The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation: A New Synthetic Approach to Tri- and Tetraarylmethanes

The selective synthesis of multiarylated acetonitriles via sequential palladium-catalyzed arylations of chloroacetonitrile is reported. The three aryl groups are installed via a Pd-catalyzed Suzuki-Miyaura cross coupling reaction followed by back-to-back C-H arylations to afford triarylacetonitriles in three steps with no over-arylation at any step. The triarylacetonitrile products can be converted into highly functionalized species including tetraarylmethanes. This new strategy provides rapid access to a variety of unsymmetrical tri- and tetraarylmethane derivatives from simple, readily available starting materials. (Chemical Presented)