Author: Jessica.F

Oxidation of alcohols by transition metal complexes. Part III. The reduction of aldimines by hydrogen transfer from propan-2-ol catalyzed by rhodium complexes was written by Grigg, Ronald;Mitchell, Thomas R. B.;Tongpenyai, Ngampong. And the article was included in Synthesis in 1981.Category: nitriles-buliding-blocks This article mentions the following:

Benzaldimines 4-RC₆H₄CH:NCH₂Ph (R = H, Me, MeO, Cl, CF₃) and I (R¹ = H, MeO, Cl, CF₃, cyano; R² = H, MeO, Cl, CF₃, cyano) reacted with Me₂CHOH and a Rh complex to yield the resp. 4-RC₆H₄CH₂NHCH₂Ph and II. A mixture of PhCH:NCH₂Ph, RhCl(PPh₃)₃, and Na₂CO₃ in Me₂CHOH was refluxed 60 min to give ∼90% (Ph₂CH₂)₂NH. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Category: nitriles-buliding-blocks).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. 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. Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Photocatalytic C-H Amination of Aromatics Overcoming Redox Potential Limitations was written by Morofuji, Tatsuya;Ikarashi, Gun;Kano, Naokazu. And the article was included in Organic Letters in 2020.Computed Properties of C8H8N2O This article mentions the following:

The photocatalytic C-H amination of aromatics overcoming redox potential limitations was reported. Radical cations of aromatic compounds were generated photocatalytically using Ru(phen)₃(PF₆)₂, which had a reduction potential at a high oxidation state (E_red(Ru^III/Ru^II) = +1.37 V vs SCE) lower than the oxidation potentials of aromatic substrates (E_ox = +1.65 to +2.27 V vs SCE). The radical cations were trapped with pyridine to give N-arylpyridinium ions, which were converted to aromatic amines. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Computed Properties of C8H8N2O).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Computed Properties of C8H8N2O

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery and Characterization of MAPK-activated Protein Kinase-2 Prevention of Activation Inhibitors was written by Cumming, John G.;Debreczeni, Judit E.;Edfeldt, Fredrik;Evertsson, Emma;Harrison, Martin;Holdgate, Geoffrey A.;James, Michael J.;Lamont, Scott G.;Oldham, Keith;Sullivan, Jane E.;Wells, Stuart L.. And the article was included in Journal of Medicinal Chemistry in 2015.Quality Control of 3-Amino-4-methylbenzonitrile This article mentions the following:

Two structurally distinct series of novel, MAPK-activated kinase-2 prevention of activation inhibitors have been discovered by high throughput screening. Preliminary structure-activity relationship (SAR) studies revealed substructural features that influence the selective inhibition of the activation by p38α of the downstream kinase MK2 in preference to an alternative substrate, MSK1. Enzyme kinetics, surface plasmon resonance (SPR), 2D protein NMR, and x-ray crystallog. were used to determine the binding mode and the mol. mechanism of action. The compounds bind competitively to the ATP binding site of p38α but unexpectedly with higher affinity in the p38α-MK2 complex compared with p38α alone. This observation is hypothesized to be the origin of the substrate selectivity. The two lead series identified are suitable for further investigation for their potential to treat chronic inflammatory diseases with improved tolerability over previously studied p38α inhibitors. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Quality Control of 3-Amino-4-methylbenzonitrile).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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. 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. Quality Control of 3-Amino-4-methylbenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ruthenium-Catalyzed Direct Reductive Amination in HCOOH/NEt₃ Mixture was written by Zhu, Mengping. And the article was included in Catalysis Letters in 2014.Reference of 10282-32-3 This article mentions the following:

Abstract: A one-pot direct reductive amination of aldehydes with primary and secondary amines using Noyori’s catalyst (η⁶-arene)Ru(H)TsDPEN in neat HCOOH/NEt₃ mixture has been developed. The catalyst formed in situ allows full conversion of aldehydes with high selectivities towards the desired amine products within hours or even minutes at room temperature For aromatic aldehydes, both 5:2 and 5:3 HCOOH/NEt₃ mixtures prove to be suitable reaction media, with the former affording higher selectivities while the latter leading to much faster reaction rates. For aliphatic aldehydes, the 5:3 HCOOH/NEt₃ mixture gives much higher selectivities due to the minimal loss from aldol condensation. This method has great application potential for the synthesis of amine products given the mild conditions. Graphical Abstract: [Figure not available: see full text.]. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Reference of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Reference of 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

N-Alkylation of amines with alcohols over nanosized zeolite beta was written by Reddy, Marri Mahender;Kumar, Macharla Arun;Swamy, Peraka;Naresh, Mameda;Srujana, Kodumuri;Satyanarayana, Lanka;Venugopal, Akula;Narender, Nama. And the article was included in Green Chemistry in 2013.Formula: C14H12N2 This article mentions the following:

Direct N-alkylation of amines with alcs. was successfully performed by using nanosized zeolite beta, which showed the highest catalytic activity among other conventional zeolites. This method has several advantages, such as eco-friendliness, moderate to high yields, and simple work-up procedure. The catalyst was successfully recovered and reused without significant loss of activity and only water is produced as co-product. In addition, imines were also efficiently prepared from the tandem reactions of amines with 2-, 3- and 4-nitrobenzyl alcs. using nanosized zeolite beta. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Formula: C14H12N2).

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. 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.Formula: C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Highly Enantioselective Iridium-Catalyzed Hydrogenation of o-Amidophenyl Ketones Enabled by 1,2-Diphenylethylenediamine-Derived P,N,N-Ligands with Tertiary Amine Terminus was written by Wan, Yin-Bo;Hu, Xiang-Ping. And the article was included in Organic Letters in 2022.SDS of cas: 53312-77-9 This article mentions the following:

A readily available and highly modular class of chiral P,N,N-ligands based on a structurally flexible nonchiral phosphine-amine framework with an optically active 1,2-diphenylethylenediamine unit bearing a tertiary amine terminus as the chiral source were developed and successfully applied in the Ir-catalyzed asym. hydrogenation of o-amidophenyl ketones. These tridentate P,N,N-ligands exhibited excellent activity, enantioselectivity, and substrate tolerance, thus furnishing various optically active o-amidobenzhydrols in up to 99% yields and with >99% ee. The utility of this protocol was proven by synthetically diverse product transformation and highly enantioselective production of a rice plant growth regulator, (S)-inabenfide. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9SDS of cas: 53312-77-9).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.SDS of cas: 53312-77-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

P(RNCH₂CH₂)₃N: an efficient promoter for the synthesis of 3-substituted coumarins was written by Kisanga, Philip;Fei, Xiangshu;Verkade, John. And the article was included in Synthetic Communications in 2002.Synthetic Route of C14H14N2O2 This article mentions the following:

The title compounds wherein R = Me or i-Pr function as efficient promoters for the formation of coumarins in good to excellent yields (80-95%) from salicylaldehydes and di-activated methylene compounds of the type R’CH₂CO₂Et (R’ = CO₂Et, COMe, CN). Although the yields are not generally superior to those reported in the literature, the methodol. applied here is more convenient in that milder conditions and shorter reaction times are facilitated by the use of the aforementioned com. available catalysts. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Synthetic Route of C14H14N2O2).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Synthetic Route of C14H14N2O2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A efficient protocol for the synthesis of thioamides in [DBUH][OAc] at room temperature was written by Cao, Xian-Ting;Qiao, Li;Zheng, Hui;Yang, Hui-Yong;Zhang, Peng-Fei. And the article was included in RSC Advances in 2018.HPLC of Formula: 63968-85-4 This article mentions the following:

A novel, simple and eco-friendly method to synthesize thioamides from aryl nitriles and sodium sulfide (Na₂S·9H₂O) catalyzed by 1,8-diazabicyclo[5,4,0]undec-7-enium acetate ([DBUH][OAc]) ionic liquid (IL) at room temperature was developed. In this reaction, readily available inorganic salt (Na₂S·9H₂O) served as the sulfur source and various functional groups of aryl nitriles were well tolerated at room temperature In addition, the products were easily separated from the IL which could be reused at least five times without considerable loss of its activity and applied in the green, concise synthesis of ethionamide. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4HPLC of Formula: 63968-85-4).

2-(Trifluoromethoxy)benzonitrile (cas: 63968-85-4) 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.HPLC of Formula: 63968-85-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Assembly of Furazan-Fused Quinolines via an Expeditious Metal-Free [2+2+1] Radical Tandem Cyclization Process was written by Deng, Guobo;Zhong, Ronglin;Song, Jianxin;Choy, Pui Ying;Kwong, Fuk Yee. And the article was included in Organic Letters in 2021.Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

A [2+2+1]-NO-segment-incorporating heteroannulative cascade is described. This versatile method, particularly using modular cyanoarylated ketimine substrates 2-CN-3-R-4-R¹-5-R²C₆HN=C(Me)Ar (Ar = 3-methylphenyl, 4-bromophenyl, thiophen-2-yl, etc.; R = H, Br; R¹ = H, Br; R² = H, Me, F, Cl, Br, MeO, CF₃), allows efficient access to structurally diversified quinolines embedded with an oxadiazole core I. This metal-free protocol proceeds smoothly at 30°C, offers easy manipulation of substituents on the quinoline moiety, and tolerates a spectrum of functional groups. D. functional theory calculation revealed that the cyano moiety is crucial to facilitate the early cyclization step in this heteroannulation process and is different from the previously established late cyclization mechanistic interpretation. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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 2-Amino-4-(trifluoromethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Inverse gas chromatography for identification of poly(ethylene glycol adipate) and tripropionitrilamine on the surface of polymeric sorbent was written by Kudasheva, F. Kh.;Guskov, V. Yu.;Ganieva, A. G.. And the article was included in Protection of Metals and Physical Chemistry of Surfaces in 2014.Recommanded Product: 7528-78-1 This article mentions the following:

Identification of the adsorption of poly(ethylene glycol adipate) (PEGA) and tris(2-cyanoethyl)amine (TPA) on styrene-divinylbenzene porous polymer was performed with the use of the inverse gas-chromatog. method in finite concentration PEGA and TPA were applied in quantities ω = 10-6-10-3 mass fractions. As test sorbates n-propanol, n-butanol, and n-hexane used. The adsorption isotherm and the values of specific retention volumes were calculated via the Glueckauf method. It was found that the dependence of the retention volumes on the sorbate concentration in gas phase of the studied samples is well approximated by a power function corresponding to the Freundlich isotherm. The possibility of detecting PEGA and TPA on the surface of sorbent through the A coefficients of a power function was shown, and a linear dependence between the A values and neg. logarithm of ω was also found, making it possible to quant. determine TPA and PEGA on the surface of a sorbent. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Recommanded Product: 7528-78-1).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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. 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. Recommanded Product: 7528-78-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts