32327-69-8

Usage

Uses

Used in Perfumery Industry:
Benzenepropanenitrile, 4-Methylis used as a fragrance ingredient for its floral, cherry-like scent, contributing to the creation of various perfume compositions.
Used in Flavor Industry:
In the flavor industry, Benzenepropanenitrile, 4-Methylis employed as a flavoring agent, enhancing the taste profiles of different food and beverage products by imparting a subtle cherry-like flavor.
Used in Pharmaceutical Industry:
Benzenepropanenitrile, 4-Methylserves as an essential building block in the synthesis of various pharmaceutical compounds, playing a crucial role in the development of new medications.
Used in Organic Synthesis:
As a precursor in organic synthesis, Benzenepropanenitrile, 4-Methylis utilized in the production of a wide range of organic compounds, showcasing its versatility and importance in the field of chemistry.

Upstream product

• 95-47-6 o-xylene 
• 107-13-1 acrylonitrile 
• 104-82-5 4-Methylbenzyl chloride 
• 590-17-0 cyanomethyl bromide 
• 106-42-3 para-xylene 
• 75-05-8 acetonitrile 
• 151-50-8 potassium cyanide 
• 59584-38-2 α-benzenesulfonyl-4-methyl-cinnamonitrile 
• 35121-92-7 3-(4-methylphenyl)-prop-2-enyl nitrile 
• 104-87-0 4-methyl-benzaldehyde 
• 105-34-0 methyl 2-cyanoacetate 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 1431794-52-3 potassium trifluoro(4-methylphenethyl)borate 
• 622-97-9 1-ethenyl-4-methylbenzene 

Downstream Products

• 1505-50-6 3-(4-Methylphenyl)propanoic acid 
• 54930-39-1 3-(4-methylphenyl)propanamine 
• 100988-15-6 5-(2-p-Tolyl-ethyl)-[1,3,4]thiadiazol-2-ylamine 
• 141422-02-8 7-Chloro-6-nitro-2-(2-p-tolyl-ethyl)-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one 
• 141421-80-9 7-Hydroxy-6-nitro-2-(2-p-tolyl-ethyl)-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one 
• 100987-54-0 7-Amino-6-nitro-2-(2-p-tolyl-ethyl)-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one 
• 101302-80-1 6-(2-p-Tolyl-ethyl)-3H-[1,3,4]thiadiazolo[3,2-a][1,2,3]triazolo[4,5-d]pyrimidin-9-one 
• 141421-58-1 7-Hydroxy-2-(2-p-tolyl-ethyl)-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one 

Relevant academic research and scientific papers

Electrochemical Tandem Olefination and Hydrogenation Reaction with Ammonia

An electrochemical Horner-Wadsworth-Emmons/hydrogenation tandem reaction was achieved using ammonia as electron and proton donors. The reaction could give two-carbon-elongated ester and nitrile from aldehyde or ketones directly. This reaction could proceed with a catalytic amount of base or even without a base. The ammonia provides both the electron and proton for this tandem reaction and enables the catalyst-free hydrogenation of an α,β-unsaturated HWE intermediate. More than 40 examples were reported, and functional groups, including heterocycles and hydroxyl, were tolerated.

A Titanium-Catalyzed Reductive α-Desulfonylation

A titanium(III)-catalyzed desulfonylation gives access to functionalized alkyl nitrile building blocks from α-sulfonyl nitriles, circumventing traditional base-mediated α-alkylation conditions and strong single electron donors. The reaction tolerates numerous functional groups including free alcohols, esters, amides, and it can be applied also to the α-desulfonylation of ketones. In addition, a one-pot desulfonylative alkylation is demonstrated. Preliminary mechanistic studies indicate a catalyst-dependent mechanism involving a homolytic C?S cleavage.

Nickel/Cobalt-Catalyzed Reductive Hydrocyanation of Alkynes with Formamide as the Cyano Source, Dehydrant, Reductant, and Solvent

A Ni/Co co-catalyzed reductive hydrocyanation of various alkynes was developed for the production of saturated nitriles. Hydrocyanic acid is generated in situ from safe and readily available formamide. Formamide played multiple roles as a cyano source, dehydrant, and reductant for the NiII pre-catalyst and vinyl nitriles, along with acting as the co-solvent in this reaction. Detailed mechanistic investigation supported a pathway via hydrocyanation of C≡C bond and the subsequent reduction of C=C bond. Wide substrate scope, the employment of a cheap and stable nickel salt as pre-catalyst, a safe cyano source and convenient experimental operation render this hydrocyanation practical for the laboratory synthesis of saturated nitriles. (Figure presented.).

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.

Preparation method of alkyl nitrile compound

The invention discloses a preparation method of an alkyl nitrile compound. Specifically, the preparation method comprises the following step: in an organic solvent, in the presence of a protective gasand under the action of a catalyst, carrying out a reduction reaction as shown in the specification on olefin as shown in a formula I, a cyanation reagent and water, wherein the alkyl nitrile compound 1 is a compound II and/or a compound III. The preparation method provided by the invention is mild in condition, can realize hydrocyanation of olefin more safely and efficiently, and has good substrate universality and functional group compatibility.

Visible- And UV-Light-Induced Decarboxylative Radical Reactions of Benzoic Acids Using Organic Photoredox Catalysts

Photoinduced decarboxylative radical reactions of benzoic acids with electron-deficient alkenes, diborane, and acetonitrile under organic photoredox catalysis conditions and mild heating afforded adducts, arylboronate esters, and the reduction product, respectively. The reaction is thought to involve single-electron transfer promoted the generation of aryl radicals via decarboxylation. A diverse range of benzoic acids were found to be suitable substrates for this photoreaction. Only our two-molecule organic photoredox system can work well for the direct photoinduced decarboxylation of benzoic acids.

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.

Synthesis of Nitriles from Aldehydes with Elongation of the Molecule with Two Carbon Atoms

A new protocol for the synthesis of nitriles from carbonyl compounds with elongation of the molecule with two carbon atoms was developed. It involves a reaction of ethyl cyanoacetate with different aldehydes in the presence of iron pentacarbonyl as a redu

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.

Formal reductive addition of acetonitrile to aldehydes and ketones

An efficient and highly productive rhodium-catalyzed method for the synthesis of nitriles employing aldehydes or ketones, methyl cyanoacetate, water and carbon monoxide as starting materials has been developed. Simple rhodium chloride without any ligands can be used. The fine tuning of the substrate can lead to the activity higher than 5000 TON.