25468-86-4

Usage

Uses

Used in Pharmaceutical Industry:
Benzenepropanenitrile, 4-fluorois utilized as an intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with specific therapeutic properties, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, Benzenepropanenitrile, 4-fluoroserves as a key intermediate in the production of agrochemicals. Its incorporation into these compounds can enhance their effectiveness in agricultural applications, such as pest control and crop protection.
Used in Organic Synthesis:
Benzenepropanenitrile, 4-fluorois employed as a building block in the synthesis of a wide range of organic compounds. Its versatility in chemical reactions makes it a valuable component in creating diverse organic molecules for various applications.
Used in Drug Development:
Due to its potential to modulate biological activity, Benzenepropanenitrile, 4-fluorois explored in drug development for its capacity to contribute to the creation of novel therapeutic agents. Its unique properties may lead to the discovery of new medicines with improved efficacy and safety profiles.

Upstream product

• 24654-48-6 3-(4-fluorophenyl)acrylonitrile 
• 459-56-3 4-fluorobenzylic alcohol 
• 16640-68-9 cyanomethylene triphenylphosphorane 
• 107-13-1 acrylonitrile 
• 459-31-4 3-(4-fluorophenyl)propanoic acid 
• 405-99-2 para-fluorostyrene 
• 23741-79-9 Isopropylmalonsauredinitril 
• 459-57-4 4-fluorobenzaldehyde 
• 625-28-5 Isovaleronitrile 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 105-34-0 methyl 2-cyanoacetate 
• 459-46-1 4-Fluorobenzyl bromide 
• 75-05-8 acetonitrile 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 88742-89-6 5-[2-(4-Fluoro-phenyl)-ethyl]-[1,3,4]thiadiazol-2-ylamine 
• 1403029-82-2 3-(4-fluorophenyl)propyl carbamic acid methyl ester 
• 1017789-58-0 8-fluoro-2,3,4,5-tetrahydro-benzo[c]azepin-1-one 
• 101488-65-7 3-(4-fluorophenyl)propan-1-amine 
• 54930-39-1 3-(4-methylphenyl)propanamine 
• 141447-03-2 7-Chloro-2-[2-(4-fluoro-phenyl)-ethyl]-6-nitro-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one 
• 141421-86-5 2-[2-(4-Fluoro-phenyl)-ethyl]-7-hydroxy-6-nitro-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one 
• 100987-57-3 7-Amino-2-[2-(4-fluoro-phenyl)-ethyl]-6-nitro-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one 
• 101302-83-4 6-[2-(4-Fluoro-phenyl)-ethyl]-3H-[1,3,4]thiadiazolo[3,2-a][1,2,3]triazolo[4,5-d]pyrimidin-9-one 
• 141421-64-9 2-[2-(4-Fluoro-phenyl)-ethyl]-7-hydroxy-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one 
• 465528-50-1 2-{(1-(3-[4-chlorophenyl]propyl)aminocarbonyl)cyclopentylmethyl}-4-methoxybutyric acid tert-butyl ester 
• 46459-22-7 2-(4-fluoro-phenethyl)-5,6-dihydro-4H-[1,3]thiazine 

Relevant academic research and scientific papers

CO2-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions**

Thermodynamic and kinetic control of a chemical process is the key to access desired products and states. Changes are made when a desired product is not accessible; one may manipulate the reaction with additional reagents, catalysts and/or protecting groups. Here we report the use of carbon dioxide to accelerate cyanohydrin synthesis under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN. Under inert atmosphere, the reaction is essentially not operative due to the unfavored equilibrium. The utility of CO2-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani–Fischer synthesis under neutral conditions. This protocol offers an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atmospheric pressure of CO2.

8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study

β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.

Overcoming Selectivity Issues in Reversible Catalysis: A Transfer Hydrocyanation Exhibiting High Kinetic Control

Reversible catalytic reactions operate under thermodynamic control, and thus, establishing a selective catalytic system poses a considerable challenge. Herein, we report a reversible transfer hydrocyanation protocol that exhibits high selectivity for the thermodynamically less favorable branched isomer. Selectivity is achieved by exploiting the lower barrier for C-CN oxidative addition and reductive elimination at benzylic positions in the absence of a cocatalytic Lewis acid. Through the design of a novel type of HCN donor, a practical, branched-selective, HCN-free transfer hydrocyanation was realized. The synthetically useful resolution of a mixture of branched and linear nitrile isomers was also demonstrated to underline the value of reversible and selective transfer reactions. In a broader context, this work demonstrates that high kinetic selectivity can be achieved in reversible transfer reactions, thus opening new horizons for their synthetic applications.

Nickel-Catalyzed Markovnikov Transfer Hydrocyanation in the Absence of Lewis Acid

Hydrocyanation in the absence of toxic HCN gas is highly desirable. Addressing that challenge, transition-metal-catalyzed transfer hydrocyanation using safe HCN precursors has been developed, but these reagents generally require a Lewis acid for activation, and the control of regioselectivity often remains problematic. In this Letter, a Ni-catalyzed highly Markovnikov-selective transfer hydrocyanation that operates in the absence of any Lewis acid is reported. The readily prepared pro-aromatic 1-isopropylcyclohexa-2,5-diene-1-carbonitrile is used as the HCN source, and the reaction shows a broad substrate scope and high functional group tolerance. Terminal styrene derivatives, dienes, and internal alkynes are converted with good to excellent selectivities. Mechanistic studies provide insights into the origin of the regioselectivity.

Design, synthesis and biological evaluation of 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one derivatives as potent β2-adrenoceptor agonists

A series of β2-adrenoceptor agonists with an 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one moiety is presented. The stimulatory effects of the compounds on human β2-adrenoceptor and β1-adrenoceptor were characterized by a cell-based assay. Their smooth muscle relaxant activities were tested on isolated guinea pig trachea. Most of the compounds were found to be potent and selective agonists of the β2-adrenoceptor. One of the compounds, (R)-18c, possessed a strong β2-adrenoceptor agonistic effect with an EC50 value of 24 pM. It produced a full and potent airway smooth muscle relaxant effect same as olodaterol. Its onset of action was 3.5 min and its duration of action was more than 12 h in an in vitro guinea pig trachea model of bronchodilation. These results suggest that (R)-18c is a potential candidate for long-acting β2-AR agonists.

Adenosine receptor antagonists

The invention provides a compound shown as a formula (I) and a pharmaceutical composition thereof. The compounds of formula (I) of the present invention are useful as adenosine receptor inhibitors, especially A2A and/or A2B inhibitors, for example, the product can be used for prevention or treatment of diseases associated with A2A and/or A2B activity or expression.

Identification of 2,6-Disubstituted 3 H-Imidazo[4,5- b]pyridines as Therapeutic Agents for Dysferlinopathies through Phenotypic Screening on Patient-Derived Induced Pluripotent Stem Cells

Dysferlinopathies, which are muscular diseases caused by mutations in the dysferlin gene, remain serious medical problems due to the lack of therapeutic agents. Herein, we report the design, synthesis, and structure-activity relationships of a 2,6-disubst

Transition-metal-free Intramolecular C-H amination of sulfamate esters and: N -alkylsulfamides

The transition-metal-free intramolecular C-H amination of sulfamate esters using iodine oxidants, tert-butyl hypoiodite (t-BuOI) and N-iodosuccinimide (NIS) is reported. A method using NIS was also successfully applied to the oxidative cyclization of N-alkylsulfamides.

Process for the Catalytic Reversible Alkene-Nitrile Interconversion

The present invention refers to processes for catalytic reversible alkene-nitrile interconversion through controllable HCN-free transfer hydrocyanation.

Efficient nickel-catalyzed hydrocyanation of alkenes using acetone cyanohydrin as a safer cyano source

An active nickel catalyst prepared in situ from a Ni(II) compound, phosphine ligand, and zinc powder was found to be an efficient catalyst system for the hydrocyanation of various alkenes using acetone cyanohydrin as a safer cyano source. The combination of NiCl2·6H2O and 1,3-bis(diphenylphosphino)propane was the most efficient catalyst precursor in DMF. Under the optimized conditions, various styrenes, heterocyclic alkenes, and aliphatic alkenes were converted to their corresponding nitriles in excellent yields.