719-82-4

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-Fluorophenyl)-2-phenylacetonitrile is used as a reagent in the synthesis of unsymmetric triarylacetonitriles, which are valuable intermediates in the development of pharmaceutical compounds. The palladium-catalyzed sequential arylations from chloroacetonitrile allow for the creation of complex molecular structures that can be further converted to triand tetraarylmethanes, enhancing the diversity and effectiveness of drug candidates.
Used in Chemical Research:
In the field of chemical research, 2-(4-Fluorophenyl)-2-phenylacetonitrile serves as a key building block for the synthesis of various organic compounds with potential applications in materials science, agrochemicals, and other specialized industries. Its unique structural features make it a versatile component in the design and synthesis of novel molecules with tailored properties.
Used in Material Science:
2-(4-Fluorophenyl)-2-phenylacetonitrile is utilized in the development of new materials with specific properties, such as improved thermal stability, enhanced electrical conductivity, or unique optical characteristics. The incorporation of 2-(4-fluorophenyl)-2-phenyl-acetonitrile into polymers or other materials can lead to the creation of advanced materials for use in various high-tech applications.
Overall, 2-(4-Fluorophenyl)-2-phenylacetonitrile is a versatile and valuable compound with a wide range of applications across different industries, particularly in the synthesis of complex organic molecules and the development of innovative materials.

InChI:InChI=1/C14H10FN/c15-13-8-6-12(7-9-13)14(10-16)11-4-2-1-3-5-11/h1-9,14H

Upstream product

• 462-06-6 fluorobenzene 
• 5798-79-8 bromo-phenyl-acetonitrile 
• 71-43-2 benzene 
• 459-22-3 4-fluorophenylacetonitrile 
• 133721-87-6 2-(4-fluorophenyl)-2-hydroxyacetonitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 149099-27-4 4-fluorobenzhydrol 
• 140-29-4 phenylacetonitrile 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 88675-31-4 2-bromo-1-(4-fluorophenyl)-2-phenylethan-1-one 
• 347-84-2 1-(4-fluorophenyl)-2-phenylethanone 
• 1582-01-0 4-fluorophenyl tosylate 
• 98-80-6 phenylboronic acid 

Downstream Products

• 2927-79-9 2-(4-fluoro-phenyl)-2-phenyl-ethylamine 
• 324008-27-7 2-(4-fluoro-phenyl)-2-phenyl-thioacetamide 
• 324008-32-4 2-(2-{2-[(4-fluoro-phenyl)-phenyl-methyl]-thiazol-4-yl}-ethyl)-isoindole-1,3-dione 
• 345-83-5 4-fluorobenzophenone 

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

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.

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.

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)

Zn(OTf)2 - Catalyzed direct cyanation of benzylic alcohols - A novel synthesis of α-aryl nitriles

This work demonstrates an efficient method to prepare α-aryl nitriles by direct cyanation of benzylic alcohol with TMSCN in the presence of a catalytic amount of Zn(OTf)2 under heating condition. A variety of benzylic alcohols can be converted into the corresponding α-aryl nitriles in good to excellent yields. 2012 Elsevier Ltd. All rights reserved.

Histamine H1 receptor ligands - Part II. Synthesis and in vitro pharmacology of 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives

New 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives were prepared and tested in vitro as H1 receptor antagonists. The compounds with 2-phenylamino substitution with meta-halide substituents at the phenyl ring, showed weak H1-antagonistic activity (pA2: 4.62-5.04) and this activity was completely lost in the case of meta-methyl substituent (pA2 : 4). When the phenylamino group was replaced by benzhydryl groups of classic antihistamines, the resulting compounds exhibited slightly improved H1-antagonistic activity (at the meta-position pA2: 6.38-6.15; at the para-position pA2: 6.04-5.87).

Condensed heterocyclic compounds, their production and use

The compound STR1 wherein ring A represents a benzene ring; Ar represents an aromatic group; R 1 and R 2 independently represent hydrogen, acyl or hydrocarbon group or R 1 and R 2 taken together with the adjacent nitrogen atom represent a nitrogen-contain

Phenyl-substituted normethadones: Synthesis and pharmacology

Phenyl-substituted normethadone derivatives were synthesized and their affinity (IC50) for opioid receptors was determined by displacement of the specific binding sites of [3H]sufentanyl on rat brain preparations. Substitution resulted in a decrease of affinity in-vitro. These results suggest that normethadone-like compounds may interact with the P subsite of the μ-opioid receptor and that the P subsite has a well-defined cavity shape of stringent dimensions.