Author: Jessica.F

Selective Synthesis of Secondary and Tertiary Amines by Reductive N-Alkylation of Nitriles and N-Alkylation of Amines and Ammonium Formate Catalyzed by Ruthenium Complex was written by Alshakova, Iryna D.;Nikonov, Georgii I.. And the article was included in ChemCatChem in 2019.HPLC of Formula: 4714-63-0 This article mentions the following:

A ruthenium catalytic system for the syntheses of secondary and tertiary amines via reductive N-alkylation of nitriles and N-alkylation of primary amines is proposed. Isomeric ruthenium complexes catalyzed transfer hydrogenation and N-alkylation of nitriles in ethanol to give secondary amines. Unsym. secondary amines can be produced by N-alkylation of primary amines with alcs. via the borrowing hydrogen methodol. Aliphatic amines were obtained with excellent yields, while only moderate conversions were observed for anilines. Based on kinetic and mechanistic studies, it is suggested that the rate determining step is the hydrogenation of intermediate imine to amine. Finally, ammonium formate was applied as the amination reagent for alcs. in the presence of ruthenium catalyst. Secondary amines were obtained from primary alcs. within 24 h at 100 °C, and tertiary amines can be produced after prolonged heating. Secondary alcs. can only be converted to secondary amines with moderate yield. Based on mechanistic studies, the process is suggested to proceed through an ammonium alkoxy carbonate intermediate, where carbonate acts as an efficient leaving group. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0HPLC of Formula: 4714-63-0).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.HPLC of Formula: 4714-63-0

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Nucleophilic and Radical Heptafluoroisopropoxylation with Redox-Active Reagents was written by Tong, Chao-Lai;Xu, Xiu-Hua;Qing, Feng-Ling. And the article was included in Angewandte Chemie, International Edition in 2021.Category: nitriles-buliding-blocks This article mentions the following:

The practical and efficient heptafluoroisopropoxylation reactions through the invention of a series of redox-active N-OCF(CF₃)₂ reagents e.g., I were described. These reagents were readily prepared from the oxidative heptafluoroisopropylation of hydroxylamines e.g., II with AgCF(CF₃)₂. The substitutions on the nitrogen atom significantly affected the properties and reactivities of N-OCF(CF₃)₂ reagents. Accordingly, two types of N-OCF(CF₃)₂ reagents including I and III were used as OCF(CF₃)₂ anion and radical precursors, resp. This protocol enables the direct heptafluoroisopropoxylation of a range of substrates, delivering the corresponding products in moderate to excellent yields. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Category: nitriles-buliding-blocks).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Category: nitriles-buliding-blocks

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Divergent synthesis of 2-methylthioindole and 2-unsubstituted indole derivatives mediated by SOCl₂ and dimethyl/diethyl sulfoxides was written by Zhang, Jingran;Zhang, Beibei;He, Jiaxin;Shi, Haofeng;Du, Yunfei. And the article was included in Organic & Biomolecular Chemistry in 2022.Application of 1483-54-1 This article mentions the following:

A metal-free divergent synthesis of indole compounds dependent on a reagent via intramol. C(sp²)-H amination was described. The reaction of 2-vinylanilines with DMSO/SOCl₂ at 70 ° was found to give 2-thiomethylindoles, while replacing DMSO with di-Et sulfoxide afforded 2-unsubstituted indoles in a highly selective manner. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Application of 1483-54-1).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Application of 1483-54-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Exploring Homogeneous Conditions for Mild Buchwald-Hartwig Amination in Batch and Flow was written by Kashani, Saeed K.;Jessiman, Jacob E.;Newman, Stephen G.. And the article was included in Organic Process Research & Development in 2020.Name: 4-(Benzylamino)benzonitrile This article mentions the following:

The use of high throughput experimentation to identify a number of conditions that enable Buchwald-Hartwig reactions to be carried out using readily available ligands (e.g. XantPhos) with DBU as a soluble, functional group tolerant, homogeneous base was described. Application of this system to diverse aminations in batch and flow were demonstrated, as was the translation of this technique to performing continuous Mizoroki-Heck and Sonogashira coupling reactions. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Name: 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Name: 4-(Benzylamino)benzonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A novel multiple-stage antimalarial agent that inhibits protein synthesis was written by Baragana, Beatriz;Hallyburton, Irene;Lee, Marcus C. S.;Norcross, Neil R.;Grimaldi, Raffaella;Otto, Thomas D.;Proto, William R.;Blagborough, Andrew M.;Meister, Stephan;Wirjanata, Grennady;Ruecker, Andrea;Upton, Leanna M.;Abraham, Tara S.;Almeida, Mariana J.;Pradhan, Anupam;Porzelle, Achim;Martinez, Maria Santos;Bolscher, Judith M.;Woodland, Andrew;Luksch, Torsten;Norval, Suzanne;Zuccotto, Fabio;Thomas, John;Simeons, Frederick;Stojanovski, Laste;Osuna-Cabello, Maria;Brock, Paddy M.;Churcher, Tom S.;Sala, Katarzyna A.;Zakutansky, Sara E.;Jimenez-Diaz, Maria Belen;Sanz, Laura Maria;Riley, Jennifer;Basak, Rajshekhar;Campbell, Michael;Avery, Vicky M.;Sauerwein, Robert W.;Dechering, Koen J.;Noviyanti, Rintis;Campo, Brice;Frearson, Julie A.;Angulo-Barturen, Inigo;Ferrer-Bazaga, Santiago;Gamo, Francisco Javier;Wyatt, Paul G.;Leroy, Didier;Siegl, Peter;Delves, Michael J.;Kyle, Dennis E.;Wittlin, Sergio;Marfurt, Jutta;Price, Ric N.;Sinden, Robert E.;Winzeler, Elizabeth A.;Charman, Susan A.;Bebrevska, Lidiya;Gray, David W.;Campbell, Simon;Fairlamb, Alan H.;Willis, Paul A.;Rayner, Julian C.;Fidock, David A.;Read, Kevin D.;Gilbert, Ian H.. And the article was included in Nature (London, United Kingdom) in 2015.Formula: C12H14N2O This article mentions the following:

There is an urgent need for new drugs to treat malaria, with broad therapeutic potential and novel modes of action, to widen the scope of treatment and to overcome emerging drug resistance. Here we describe the discovery of DDD107498, a compound with a potent and novel spectrum of antimalarial activity against multiple life-cycle stages of the Plasmodium parasite, with good pharmacokinetic properties and an acceptable safety profile. DDD107498 demonstrates potential to address a variety of clin. needs, including single-dose treatment, transmission blocking and chemoprotection. DDD107498 was developed from a screening program against blood-stage malaria parasites; its mol. target has been identified as translation elongation factor 2 (eEF2), which is responsible for the GTP-dependent translocation of the ribosome along mRNA, and is essential for protein synthesis. This discovery of eEF2 as a viable antimalarial drug target opens up new possibilities for drug discovery. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Formula: C12H14N2O).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Formula: C12H14N2O

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Disarming the alkoxide trap to access a practical FeCl₃ system for borrowing-hydrogen N-alkylation was written by Ye, Zongren;Yang, Zhenjie;Yang, Chenhui;Huang, Ming;Xu, Xianfang;Ke, Zhuofeng. And the article was included in Organic Chemistry Frontiers in 2022.Related Products of 10282-32-3 This article mentions the following:

Borrowing hydrogen N-alkylation is one of the most valuable transformations in organic synthesis, with high selectivity and at. economy. The general non-noble metal catalysts for borrowing hydrogen usually have limitations on operational convenience or catalytic efficiency. In particular, the development of practical and mild Fe(III) catalysis is a big challenge due to the alkoxide trap in terms of d-wall issues. Inspired by the theor. design, utilizing an in situ reaction strategy to overcome the alkoxide trap of Fe(III), authors present here a practical in situ ferric chloride and bis-(N-heterocyclic carbene) (bis-NHC) system for the borrowing-hydrogen N-alkylation of amines by alcs. under mild reaction conditions, attributed to the merits of bis-NHC in strong-field ligands, strong σ-donation and π-back-donation, and the trans effect. This system was applied to a wide range of alcs. and amines. Through comprehensive experiments and DFT calculations, the mechanism of the reaction was studied, which highlighted the roles of strong-field ligands, strong σ-donation and π-back-donation, and the trans effect by bis-NHC in ensuring the in situ reduction of Fe(III) to Fe(II) and triggering the borrowing of hydrogen under mild conditions. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Related Products of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Related Products of 10282-32-3

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Nitrile – Wikipedia,
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A facile synthesis of trifluoromethylamines by oxidative desulfurization-fluorination of dithiocarbamates was written by Kanie, Kiyoshi;Mizuno, Katsuya;Kuroboshi, Manabu;Hiyama, Tamejiro. And the article was included in Bulletin of the Chemical Society of Japan in 1998.Quality Control of 4-(Benzylamino)benzonitrile This article mentions the following:

Trifluoromethylamines are easily synthesized from dithiocarbamates by a reagent system consisting of tetrabutylammonium dihydrogen trifluoride and an N-halo imide under mild conditions. When this reaction was applied to dithiocarbamates ArN(R)CS₂Me at higher temperatures, the trifluoromethylation was accompanied by halogen substitution at the p-position of the Ar group. The synthesis of trifluoromethyl-substituted adenosine is also described. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Quality Control of 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Quality Control of 4-(Benzylamino)benzonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Cobalt encapsulated in N-doped graphene sheet for one-pot reductive amination to synthesize secondary amines was written by Liu, Lin;Li, Wenxiu;Qi, Ran;Zhu, Qingqing;Li, Jing;Fang, Yuzhen;Kong, Xiangjin. And the article was included in Molecular Catalysis in 2021.Product Details of 10282-32-3 This article mentions the following:

In this study, an efficient N-doped graphene sheet-coated cobalt catalyst (Co@CN-800) was developed through a simple pyrolysis process, which could gave 99.5% yield of N-benzylaniline by one-pot reductive amination of nitrobenzene with benzaldehyde during at least 5 cycles. Catalyst characterization and control experiments confirmed that the robust catalytic performance of the catalyst is probably due to the synergy effect of in situ generated Co-Nx encapsulated in N-doped graphene layer and appropriate meso-pore structure. Addnl., the substrate adaptability of the catalyst was proved since a variety of corresponding secondary amines RCH₂NHR¹ (R = C₆H₅, 4-pyridyl, cyclohexyl, etc.; R¹ = C₆H₅, 4-FC₆H₄, cyclohexyl, etc.) were smoothly obtained under relatively mild conditions, which makes the secondary amine synthesis strategy based on Co@CN-800 shows excellent application prospect. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Product Details of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Product Details of 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Transfer hydrogenation of nitroarenes into anilines by palladium nanoparticles via dehydrogenation of dimethylamine borane complex was written by Patil, Nilesh M.;Bhosale, Manohar A.;Bhanage, Bhalchandra M.. And the article was included in RSC Advances in 2015.Application In Synthesis of 3-Amino-4-methylbenzonitrile This article mentions the following:

This work reports a simple and highly efficient protocol for reduction of nitroarenes to corresponding amines via dehydrogenation of dimethylamine borane using palladium nanoparticles (Pd NPs) as a versatile heterogeneous catalyst. The facile approach for the synthesis of Pd NPs within 15 min in aqueous medium has been reported. The Pd NPs were well characterized using various anal. techniques such as X-ray diffraction (XRD), field emission gun scanning electron microscope (FEG-SEM), transmission electron microscopy (TEM), energy dispersive X-ray spectrum (EDAX) and X-ray photoelectron spectrum (XPS). The developed catalytic system uses environmentally benign dimethylamine borane as a reducing agent which is highly stable, water soluble and nontoxic. The various amines were synthesized from nitroarenes in excellent yields within 10-60 min at room temperature The catalyst was reused up to four successive cycles without significant loss in its catalytic activity. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Application In Synthesis of 3-Amino-4-methylbenzonitrile).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Application In Synthesis of 3-Amino-4-methylbenzonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Precision Polyethylene: Changes in Morphology as a Function of Alkyl Branch Size was written by Rojas, Giovanni;Inci, Bora;Wei, Yuying;Wagener, Kenneth B.. And the article was included in Journal of the American Chemical Society in 2009.Safety of 2-Cyclohexylacetonitrile This article mentions the following:

Metathesis polycondensation chem. has been employed to control the crystalline morphol. of a series of 11 precision-branched polyethylene structures, the branch being placed on each 21st carbon and ranging in size from a Me group to an adamantyl group. The crystalline unit cell is shifted from orthorhombic to triclinic, depending upon the nature of the precision branch. Further, the branch can be positioned either in the crystalline phase or in the amorphous phase of polyethylene, a morphol. change dictated by the size of the precision branch. This level of morphol. control is accomplished using step polymerization chem. to produce polyethylene rather than conventional chain polymerization techniques. Doing so requires the synthesis of a series of unique sym. diene monomers incorporating the branch in question, followed by ADMET polymerization and hydrogenation to yield the precision-branched polyethylene under study. Exhaustive structure characterization of all reaction intermediates as well as the precision polymers themselves is presented. A clear change in morphol. was observed for such polymers, where small branches (Me and ethyl) are included in the unit cell, while branches equal to or greater in mass than Pr are excluded from the crystal. When the branch is excluded from the unit cell, all such polyethylene polymers possess essentially the same melting temperature, regardless of the size of the branch, even for the adamantyl branch. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Safety of 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Safety of 2-Cyclohexylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts