58422-60-9

Usage

Uses

Used in Pharmaceutical Industry:
2-(o-Tolyl)propanenitrile is used as a key intermediate in the synthesis of pharmaceutical drugs for its ability to contribute to the development of new medicinal compounds. Its unique structure allows for the creation of a wide range of therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(o-Tolyl)propanenitrile is utilized as a starting material for the synthesis of various agrochemicals, playing a crucial role in the development of products that protect crops and enhance agricultural yields.
Used in Perfumery:
2-(o-Tolyl)propanenitrile is also employed in the perfume industry, where it serves as a component in the creation of fragrances, capitalizing on its chemical properties to produce distinct and desirable scents.
Safety Note:
It is important to handle 2-(o-Tolyl)propanenitrile with care due to its potential to cause irritation to the eyes and skin upon contact, emphasizing the need for proper safety measures during its use in various applications.

Upstream product

• 22364-68-7 2-tolylmethylnitrile 
• 616-38-6 carbonic acid dimethyl ester 
• 74-88-4 methyl iodide 
• 18151-58-1 2-trimethylsilylpropionitrile 
• 95-46-5 2-methylphenyl bromide 
• 7677-24-9 trimethylsilyl cyanide 
• 557-21-1 zinc(II) cyanide 
• 611-15-4 1-methyl-2-vinyl-benzene 
• 124-38-9 carbon dioxide 
• 68-12-2 N,N-dimethyl-formamide 
• 67-56-1 methanol 
• 625-28-5 Isovaleronitrile 
• 577-16-2 2-Methylacetophenone 
• 67541-85-9 4-methyl-N'-(1-(2-methylphenyl)ethylidene)benzenesulfonohydrazide 

Downstream Products

• 5266-88-6 2-o-tolyl-propylamine 
• 145611-10-5 5,5-Diethoxy-2-methyl-2-o-tolyl-pentanenitrile 
• 960595-23-7 (2R,3S)-3-hydroxy-2-methyl-2-(2-methylphenyl)-3-phenylpropanenitrile 
• 960595-44-2 (1S,2R)-2-cyano-1-phenyl-2-(2-methylphenyl)propyl-3,5-dinitrobenzoate 
• 960595-41-9 1-(1,1-dimethylethyl)-N-[2-(2-methylphenyl)-1-propenylidene]-1,1-dimethylsilanamine 
• 577-16-2 2-Methylacetophenone 
• 58422-67-6 α-Peracetoxy-α-methyl-β-o-tolylpropionitril 

Relevant academic research and scientific papers

Asymmetric Deoxygenative Cyanation of Benzyl Alcohols Enabled by Synergistic Photoredox and Copper Catalysis?

Summary of main observation and conclusion. An enantioselective deoxygenative cyanation of benzyl alcohols was accomplished for the first time through the synergistic photoredox and copper catalysis. This reaction features the use of organic photosensitizer and low-cost 3d metal catalyst, simple and safe operations, and extremely mild conditions. A variety of chiral benzyl nitriles were produced in generally good yields and high level of enantiocontrols from readily available feedstocks (22 examples, up to 93% yield and 92% ee).

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.

α-Methylation of 2-Arylacetonitrile by a Trimethylamine-Borane/CO2 System

A highly selective monomethylation of 2-arylacetonitrile using CO2 is described. The utilization of trimethylamine-borane facilitates the six-electron reduction of CO2. This reaction is the first selective six-electron reductive functionalization of CO2 faciliated by C(sp3)-H bonds. A variety of 2-arylpropionitrile was obtained in good yields. The reaction could also be applied at the gram scale.

Enantioseparation of Sulfoxides and Nitriles by Inclusion Crystallization with Chiral Organic Salts Based on l-Phenylalanine

Enantioselective inclusion of aromatic sulfoxides and nitriles was achieved in a host framework created by organic salts comprising achiral benzoic acids and a chiral primary amine (1a) derived from l-phenylalanine. Tuning of the combined achiral acid component successfully changed the chiral recognition ability of the organic salts. The guest molecules were hydrogen-bonded to form three-component inclusion crystals, and the enantiomers of nitriles and sulfoxides were separated with high selectivity up to 92 and 98 % ee. As far as we know, this is the first example of the enantioseparation of non-functionalized aromatic nitriles.

Selective α-Monomethylation by an Amine-Borane/N,N-Dimethylformamide System as the Methyl Source

A new and practical α-monomethylation strategy using an amine-borane/N,N-dimethylformamide (R3N-BH3/DMF) system as the methyl source was developed. This protocol has been found to be effective in the α-monomethylation of arylacetonitriles and arylacetamides. Mechanistic studies revealed that the formyl group of DMF delivered the carbon and one hydrogen atoms of the methyl group, and R3N-BH3 donated the remaining two hydrogen atoms. Such a unique reaction pathway enabled controllable assemblies of CDH2-, CD2H-, and CD3- units using Me2NH-BH3/d7-DMF, Me3N-BD3/DMF and Me3N-BD3/d7-DMF systems, respectively. Further application of this method to the facile synthesis of anti-inflammatory flurbiprofen and its varied deuterium-labeled derivatives was demonstrated.

Methylation of C(sp3)-H/C(sp2)-H bonds with methanol catalyzed by cobalt system

A highly efficient Co-based catalytic system, composed of a commercially available Co salt, a tetradentate phosphine ligand P-(CH2CH2PPh2)3(PP3), and a base (denoted as [Co]/PP3/base), is developed for the methylation of C(sp3)-H and C(sp2)-H bonds using methanol as a methylating reagent. The Co(BF4)2.6H2O/PP3/K2CO3 catalytic system showed high catalytic activity for the methylation of C-H bonds in aryl alkyl ketones, aryl acetonitriles, and indoles, with wide substrate scope and good functional group tolerance, and methylsubstituted products were obtained in good to excellent yields at 100 °C. This cheap, readily available, and highly efficient Co-based catalytic system may have promising applications in methylation reaction using methanol.

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.

Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "cN" Source

A novel protocol for the synthesis of α-aryl nitriles has been successfully achieved via a copper-catalyzed cyanation of N-tosylhydrazones employing thiocyanate as the source of cyanide. The features of this method include a convenient operation, readily available substrates, low-toxicity thiocyanate salts, and a broad substrate scope.

Hiyama reactions of activated and unactivated secondary alkyl halides catalyzed by a nickel/norephedrine complex

(Chemical Equation Presented) An active partner: Nickel in combination with an amino alcohol ligand (norephedrine) was found to provide the most versatile and efficient catalyst for Hiyama cross-coupling reactions of alkyl electrophiles that has been described to date. Unprecedented Hiyama reactions of activated secondary alkyl bromides were achieved, as were the first Hiyama couplings of (activated) alkyl chlorides (see scheme, X = Br, Cl; HMDS = 1,1,1,3,3,3-hexamethyldisilazane, DMA = N,N-dimethylacetamide).

Mild palladium-catalyzed selective monoarylation of nitriles

Two new palladium-catalyzed procedures for the arylation of nitriles under less basic conditions than previously reported have been developed. The selective monoarylation of acetonitrile and primary nitriles has been achieved using α-silyl nitriles in the presence of ZnF2. This procedure is compatible with a variety of functional groups, including cyano, keto, nitro, and ester groups, on the aryl bromide. The arylation of secondary nitriles occurred in high yield by conducting reactions with zinc cyanoalkyl reagents. These reaction conditions tolerated base-sensitive functional groups, such as ketones and esters. The combination of these two methods, one with a-silyl nitriles and one with zinc cyanoalkyl reagents, provides a catalytic route to a variety of benzylic nitriles, which have not only biological significance but utility as synthetic intermediates. The utility of these new coupling reactions has been demonstrated by a synthesis of verapamil, a clinically used drug for the treatment of heart disease, by a three-step route from commercial materials that allows convenient variation of the aryl group.