6575-13-9

Usage

Chemical Properties

beige crystalline powder

InChI:InChI=1/C9H9N/c1-7-4-3-5-8(2)9(7)6-10/h3-5H,1-2H3

Upstream product

• 151-50-8 potassium cyanide 
• 86364-02-5 2,6-dimethylphenyl trifluoromethanesulphonate 
• 544-92-3 copper(I) cyanide 
• 87-62-7 2,6-dimethylaniline 
• 608-28-6 2,6-dimethyliodobenzene 
• 92114-96-0 mercury fulminate 
• 108-38-3 m-xylene 
• 22884-95-3 3,4-dimethylbenzonitrile 
• 576-22-7 2-Bromo-m-xylene 
• 557-19-7 nickel cyanide 
• 6781-98-2 2,6-dimethyl-1-chlorobenzene 
• 1123-56-4 2,6-dimethylbenzaldehyde 
• 583-70-0 1-bromo-2,4-dimethylbenzene 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 2142-76-9 2',6'-dimethylacetophenone 
• 22627-02-7 1-(2,6-dimethylphenyl)1phenylmethanimine 
• 55321-98-7 2,6-dimethylbenzamide 
• 74788-82-2 (2,6-dimethylphenyl)methanamine 
• 82204-76-0 1-(2,6-dimethylphenyl)ethanimine 
• 33875-63-7 1,3-Bis(bromomethyl)benzene-2-carbonitrile 
• 632-46-2 2,6-dimethylbenzoic acid 
• 65231-43-8 2,6-Dimethyl-2'-ethylbenzophenonimin 
• 65271-59-2 N'-[1-(2,4-Dimethyl-phenyl)-1-(2,6-dimethyl-phenyl)-meth-(Z)-ylidene]-N,N-dimethyl-ethane-1,2-diamine 
• 65232-52-2 N'-[1-(2,6-Dimethyl-phenyl)-1-p-tolyl-meth-(Z)-ylidene]-N,N-dimethyl-ethane-1,2-diamine 
• 65232-54-4 N'-[Bis-(2,6-dimethyl-phenyl)-methylene]-N,N-dimethyl-ethane-1,2-diamine 
• 65271-41-2 N-[1-(2,6-Dimethyl-phenyl)-1-p-tolyl-meth-(Z)-ylidene]-N'-methyl-propane-1,3-diamine 
• 65231-44-9 2,4',6-Trimethylbenzophenonimin 
• 65231-48-3 bis(2,6-dimethylphenyl) ketimine 

Relevant academic research and scientific papers

Recyclable and Reusable Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O System for Cyanation of Aryl Chlorides with Potassium Ferrocyanide

Pd(OAc)2/XPhos–SO3Na in a mixture of poly(ethylene glycol) (PEG-400) and water is shown to be a highly efficient catalyst for the cyanation of aryl chlorides with potassium ferrocyanide. The reaction proceeded smoothly at 100 or 120?oC with K2CO3 or KOAc as base, delivering a variety of aromatic nitriles in good to excellent yields. The isolation of the crude products is facilely performed by extraction with cyclohexane and more importantly, both expensive Pd(OAc)2 and XPhos–SO3Na in PEG-400/H2O system could be easily recycled and reused at least six times without any apparent loss of catalytic efficiency. Graphical Abstract: Palladium-catalyzed cyanation of aryl chlorides with potassium ferrocyanide leading to aryl nitriles by using Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O as a highly efficient and recyclable catalytic system is described.[Figure not available: see fulltext.]

Copper-promoted cyanation of aryl iodides with N,N-dimethyl aminomalononitrile

A copper-promoted cyanation of aryl iodides has been successfully developed by using N,N-dimethyl aminomalononitrile as the cyanide source with moderate toxicity and better stability. This reaction features broad substrate scope, excellent reaction yields, readily available catalyst, and simple reaction conditions.

On-Demand Generation and Use in Continuous Synthesis of the Ambiphilic Nitrogen Source Chloramine

Herein, we demonstrate the on-demand synthesis of chloramine from aqueous ammonia and sodium hypochlorite solutions, and its subsequent utilization as an ambiphilic nitrogen source in continuous-flow synthesis. Despite its advantages in cost and atom economy, chloramine has not seen widespread use in batch synthesis due to its unstable and hazardous nature. Continuous-flow chemistry, however, provides an excellent platform for generating and handling chloramine in a safe, reliable, and inexpensive manner. Unsaturated aldehydes are converted to valuable aziridines and nitriles, and thioethers are converted to sulfoxides, in moderate to good yields and exceedingly short reaction times. In this telescoped process, chloramine is generated in situ and immediately used, providing safe and efficient conditions for reaction scale-up while mitigating the issue of its decomposition over time.

Method for catalyzing receptor-free dehydrogenation of primary amine to generate nitrile by Ru coordination compound

The invention discloses a method for catalyzing receptor-free dehydrogenation of primary amine to generate nitrile by a Ru coordination compound. The method comprises: adding a Ru coordination compound, an alkali, a primary amine and an organic solvent into a reaction test tube according to a mol ratio of 1:100:(100-500):1000-3000, and carrying out a stirring reaction under the condition of 80 to120 DEG C; and when gas chromatography monitors that the raw materials completely disappear, stopping the reaction, collecting the reaction solution, centrifuging the reaction solution, taking the supernatant, extracting with dichloromethane, merging the organic phases, drying, filtering, evaporating the organic solvent under reduced pressure to obtain a filtrate, and carrying out column chromatography purification on the filtrate to obtain the target product nitrile. According to the invention, the catalyst is good in activity, single in catalytic system, good in product selectivity, simple in subsequent treatment and good in system universality after the reaction is finished, has a good catalytic effect on various aryl, alkyl and heteroaryl substituted primary amines, and also has a gooddehydrogenation performance on secondary amines.

Acceptorless dehydrogenation of amines to nitriles catalyzed by N-heterocyclic carbene-nitrogen-phosphine chelated bimetallic ruthenium (II) complex

We have developed a clean, atom-economical and environmentally friendly route for acceptorless dehydrogenation of amines to nitriles by combining a new dual N-heterocyclic carbene-nitrogen-phosphine ligand R(CNP)2 (R = o-xylyl) with a ruthenium precursor [RuCl2(η6-C6H6)]2. In this system, the electronic and steric factors of amines had a negligible influence on the reaction and a broad range of functional groups were well tolerated. All of the investigated amines could be converted to nitriles in good yield of up to 99% with excellent selectivity. The unprecedented catalytic performance of this system is attributed to the synergistic effect of two ruthenium centers chelated by R(CNP)2 and a plausible reaction mechanism is proposed according to the active species found via in situ NMR and HRMS.

Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO

A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.

Ligand-Promoted Non-Directed C?H Cyanation of Arenes

This article reports the first example of a 2-pyridone accelerated non-directed C?H cyanation with an arene as the limiting reagent. This protocol is compatible with a broad scope of arenes, including advanced intermediates, drug molecules, and natural products. A kinetic isotope experiment (kH/kD=4.40) indicates that the C?H bond cleavage is the rate-limiting step. Also, the reaction is readily scalable, further showcasing the synthetic utility of this method.

Catalytic Cyanation Using CO2 and NH3

Li and co-workers describe the catalytic cyanation of organic halides with CO2 and NH3. In the presence of Cu2O/DABCO as the catalyst, a variety of aromatic bromides and iodides were transformed to the desired nitrile products with broad functional-group tolerance. Both 13C- and/or 15N-labeled nitriles were obtained conveniently with appropriately isotope-labeled CO2 and NH3. Construction of functionalized chemical compounds from small molecules in a highly selective and efficient manner is crucial for sustainable development. The chemical-based manufacturing sector of the future should aim to produce chemicals from very simple and abundant resources, just as nature uses CO2 and N2 to generate sugars, amino acids, and so forth. In practice, however, the utilization of CO2 for the generation of industrial products, such as drugs and related intermediates, still remains a major challenge. Here, we describe the facile cyanide-free production of high-value nitriles with CO2 and NH3 as the sole sources of carbon and nitrogen, respectively. This practical and catalytic methodology provides a unique strategy for the utilization of small molecules for sustainable and cost-effective applications. Selective cyanation of aryl halides was achieved with CO2 and NH3 as the only sources of carbon and nitrogen, respectively. In the presence of Cu catalysts under low pressure (3 atm), a variety of aromatic iodides and bromides were transformed to the desired nitrile products without the use of toxic metal cyanides. Notably, olefins, esters, amides, alcohols, and amino groups were tolerated. Mechanistic studies suggest that Cu(III)-aryl insertion by isocyanate intermediates is involved. [13C,15N]-labeled nitriles were conveniently accessible from the respective isotope-labeled CO2 and NH3 via this methodology.

Pd-Catalyzed Cyanation of (Hetero)Aryl Halides by Using Biphosphine Ligands

Tetraadamantylbiphosphine (TABP; L1), which showed superior activity in the palladium-catalyzed cyanation of 4-chloroanisole compared to standard phosphines, was synthesized as a new ligand. The generality of the new catalytic system was shown by the cyanation reaction of approximately 30 (hetero)aryl halides including hindered, electron-rich, and electron-poor aryl chlorides. These reactions constitute the first examples of using biphosphine ligands in Pd-catalyzed coupling reactions.

Selective aerobic oxidation of benzylic amines to aryl nitriles catalyzed by CuBr2/N-methyl imidazole

A convenient and efficient copper-catalyzed aerobic oxidation of primary amines to aryl nitriles was described. Various benzylic and allylic amines were selectively oxidized to the corresponding nitriles in high yields using CuBr2/NMI as the catalyst and O2 as the oxidant. The oxidation reaction profiles monitored by 1H NMR disclosed the scenario of the reaction path as well as the role of the additives. The addition of NMI increased the rate of reaction and suppressed the hydrolysis and the deamination.