16728-84-0

Usage

Uses

Used in Pharmaceutical Industry:
[(4-methylphenyl)amino]acetonitrile is used as a starting material for the synthesis of various pharmaceuticals. Its versatile chemical structure allows for the preparation of a wide range of derivatives and functionalized compounds, making it a valuable component in drug discovery and development.
Used in Agrochemical Industry:
[(4-methylphenyl)amino]acetonitrile is used as a building block in the production of agrochemicals. Its ability to form various derivatives and functionalized compounds makes it a useful component in the development of pesticides, herbicides, and other agricultural chemicals.
Used in Dye and Pigment Industry:
[(4-methylphenyl)amino]acetonitrile is used in the production of dyes and pigments. Its chemical properties allow for the creation of a variety of colored compounds, making it a valuable component in the formulation of inks, paints, and other colorants.
Used in Medicinal Chemistry Research:
[(4-methylphenyl)amino]acetonitrile is used as a subject of interest in medicinal chemistry and drug discovery research. Its potential biological activities and versatile chemical structure make it a promising candidate for the development of new therapeutic agents and pharmaceutical compounds.

InChI:InChI=1/C9H10N2/c1-8-2-4-9(5-3-8)11-7-6-10/h2-5,11H,7H2,1H3

Upstream product

• 151-50-8 potassium cyanide 
• 28141-40-4 sodium (p-toluidino)methanesulfonate 
• 50-00-0 formaldehyd 
• 106-49-0 p-toluidine 
• 64-17-5 ethanol 
• 6011-14-9 2-aminoacetonitrile hydrochloride 
• 540-61-4 2-aminoacetonitrile 
• 74-90-8 hydrogen cyanide 
• 5546-18-9 N-p-tolyl-glycine amide 
• 107-14-2 chloroacetonitrile 
• 372-09-8 cyanoacetic acid 
• 590-17-0 cyanomethyl bromide 
• 7677-24-9 trimethylsilyl cyanide 
• 3085-54-9 N-(4-methylphenyl)formamide 

Downstream Products

• 5546-18-9 N-p-tolyl-glycine amide 
• 100801-42-1 N-[1-(2-amino-ethyl)-4,5-dihydro-1H-imidazol-2-ylmethyl]-p-toluidine 
• 829-28-7 N-Nitroso-N-(4-methyl-phenylamino)-acetonitril 
• 78366-90-2 N-Cyanmethyl-N-phenacyl-p-toluidin 
• 6162-49-8 5-amino-3-(p-tolyl)-1,2,3-oxadiazol-3-ium chloride 
• 1204614-43-6 (p-tolyl)iminoacetonitrile 
• 62166-65-8 2-(p-tolyl)iminomalononitrile 

Relevant academic research and scientific papers

Synthesis of tetrazole compounds as a novel type of potential antimicrobial agents and their synergistic effects with clinical drugs and interactions with calf thymus DNA

A series of tetrazole derivatives were synthesized and characterized by NMR, IR, MS and HRMS spectroscopy. The bioactive assay manifested that most of the target compounds exhibited good antifungal activity, especially compound 6g displayed comparable or even stronger antifungal efficiency in comparison with the reference drug Fluconazole. The combination of tetrazole derivative 6g with antibacterials Chloromycin and Norfloxacin, or antifungal Fluconazole respectively was more sensitive to methicillin-resistant MRSA and Fluconazole-insensitive Aspergillus flavus. Further research revealed that compound 6g could effectively intercalate into Calf Thymus DNA to form a 6g-DNA complex which might block DNA replication to exert its good antimicrobial activities. This journal is

Aminomethylation of lithiated nicotinamide: access to new pyridolactams

New 2,3-dihydropyrrolopyridinones were conveniently prepared by trapping lithiated pyridine carboxamides with highly reactive formimines. In this Letter, we report that a wide range of N-functionalised compounds can be synthesised in one step by this process, allowing the presence of ethers, acetals or ester moieties.

Iron-catalyzed reductive strecker reaction

Strecker reaction is widely applied for the synthesis of amino acids from aldehydes, amines and cyanides. Herein, we report the FeI2-catalyzed reductive Strecker type reaction of formamides instead of aldehydes to produce amino acetonitriles. The challenging capture of carbinolamine intermediates by CN? was achieved via Fe catalysis. This approach afforded better yields than the use of Ir- or Rh-catalysts. The application ability of this methodology is demonstrated by 1) one-pot construction of (13C labeled) complex molecules from CO2 via amino acetonitrile intermediates and 2) convenient production of homologated carboxylic acids from aldehydes.

Phosphine-Mediated Bioconjugation of the 3′-End of RNA

Staudinger ligation is an attractive bio-orthogonal reaction that has been widely used to tag proteins, carbohydrates, and nucleic acids. Here, we explore the traceless variant of the Staudinger ligation for 3′-end modification of oligoribonucleotides. An azido-containing dinucleotide was used to study the ligation. Nine phosphines containing reactive groups, affinity purification tags, or photoswitch probes have been successfully obtained. The corresponding modified dinucleotides were synthesized and characterized by LC/MS. Mechanistic interpretations of the reaction are proposed, in particular, the unprecedented formation of an oxazaphospholane nucleotide derivative, which was favored by the vicinal position of 2′-N3 and 3′-OH functional groups on the terminal ribose has been observed. The post-functionalization of a 24-nt RNA with a photoactivable tag is also reported.

Homolytic pathway for the RuO4-oxidation of amines

Oxidation by RuO4 of R-NH-Me (R = p-Me-C6H4) gave, in the presence of NaCN, the hydrazine derivative R-NMe-NMe-R as main reaction product. A homolytic Me mechanism is advanced.

Design and Synthesis of Iminosydnones for Fast Click and Release Reactions with Cycloalkynes

Emerging applications in the field of chemical biology are currently limited by the lack of bioorthogonal reactions allowing both removal and linkage of chemical entities on complex biomolecules. We recently discovered a novel reaction between iminosydnones and strained alkynes leading to two products resulting from ligation and fragmentation of iminosydnones under physiological conditions. We now report the synthesis of a panel of substituted iminosydnones and the structure reactivity relationship between these compounds and strained alkyne partners. This study identified the most relevant substituents, which allow to increase the rate of the transformation and to develop a bifunctional cleavable linker with improved kinetics.

N-Arylamines Coupled with Aldehydes, Ketones, and Imines by Means of Photocatalytic Proton-Coupled Electron Transfer

A photoredox-catalyzed umpolung strategy for coupling reactions between aldehydes, ketones, imines, and N-arylamines is reported. These reactions proceed by a Br?nsted acid-activated proton-coupled electron transfer pathway, and the protocol was used to synthesize a broad scope of 1,2-amino alcohols and vicinal diamines, both of which are common motifs in biologically active natural products, pharmaceutically active molecules, and ligands.

Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes

We report the discovery of a new bioorthogonal click-and-release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target-fishing applications. This click-and-release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.

Preparation method for alpha-cyanoamine

The invention discloses a preparation method for alpha-cyanoamine. According to the method, the product alpha-cyanoamine is prepared through nucleophilic substitution in a mixed solvent in the presence of an oxidizing agent with an amine compound and cyanoacetic acid as reactants, iodide as a catalyst and sodium acetate as alkali. The catalyst used in the method has high reactivity; reaction conditions are mild; the application scope of a substrate is wide; post-treatment is convenient; the yield of the target product is high; preparation process is simple, green and environment-friendly; and used raw materials are widely available.

Cs2CO3-Promoted Direct N-Alkylation: Highly Chemoselective Synthesis of N-Alkylated Benzylamines and Anilines

Herein is described an efficient and chemoselective method for the synthesis of diversely substituted secondary amines in yields up to 98 %. Direct mono-N-alkylation of primary benzylamines and anilines with a wide range of alkyl halides is promoted by a cesium base in the absence of any additive or catalyst. The basicity and solubility of cesium carbonate in anhydrous N,N-dimethylformamide not only enables mono-N-alkylation of primary amines but also suppresses undesired dialkylation of the desired amines.