Tag: 100-200

Ezawa, Masatoshi et al. published their research in European Journal of Organic Chemistry in 2017 | CAS: 4435-14-7

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. 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.Synthetic Route of C8H13N

One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions was written by Ezawa, Masatoshi;Togo, Hideo. And the article was included in European Journal of Organic Chemistry in 2017.Synthetic Route of C8H13N This article mentions the following:

A one-pot protocol to obtain C1-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting Me vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with mol. iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alc. into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Synthetic Route of C8H13N).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. 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.Synthetic Route of C8H13N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mekheimer, Ramadan Ahmed et al. published their research in Chinese Chemical Letters in 2008 | CAS: 70291-62-2

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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.Name: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Solar thermochemical reactions. Part II. Synthesis of 2-aminothiophenes via Gewald reaction induced by solar thermal energy was written by Mekheimer, Ramadan Ahmed;Ameen, Mohamed Abdallah;Sadek, Kamal Usef. And the article was included in Chinese Chemical Letters in 2008.Name: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Green conditions were developed for the synthesis of substituted 2-aminothiophenes employing multicomponent reactions of a ketone with active methylene nitrile and elemental sulfur induced by free solar thermal energy. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Name: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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.Name: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Rajagopal, R. et al. published their research in Synthetic Communications in 2001 | CAS: 70291-62-2

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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. 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.COA of Formula: C8H8N2S

Calcined Mg-Al hydrotalcite as a heterogeneous base catalyst for Gewald aminothiophene synthesis was written by Rajagopal, R.;Jyothi, T. M.;Daniel, Thomas;Srinivasan, K. V.;Rao, B. S.. And the article was included in Synthetic Communications in 2001.COA of Formula: C8H8N2S This article mentions the following:

Calcined Mg-Al hydrotalcite (Mg/Al=4) has been conveniently employed as a heterogeneous base catalyst in the synthesis of 2-amino-3-cyanothiophenes adopting a one pot Gewald aminothiophene methodol. The compounds thus prepared included 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile, 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile, 2-amino-3-cyano-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene and 2-amino-4,5-dimethyl-3-thiophenecarbonitrile. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2COA of Formula: C8H8N2S).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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. 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.COA of Formula: C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zakirov, N. S. et al. published their research in Zhurnal Analiticheskoi Khimii in 1987 | CAS: 7528-78-1

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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. 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.Formula: C9H12N4

Use of the least squares method for estimating the sorption capability of cyano-group-containing phases in gas chromatography was written by Zakirov, N. S.. And the article was included in Zhurnal Analiticheskoi Khimii in 1987.Formula: C9H12N4 This article mentions the following:

The least squares method was used for quant. estimation of the sorption capability of cyano-group containing stationary phases in gas chromatog. separation of alcs., nitriles, and hydrocarbons. The method can be used for selection and optimization of stationary phases with respect to analyte chain length. In the experiment, the researchers used many compounds, for example, 3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1Formula: C9H12N4).

3,3′,3”-Nitrilotripropanenitrile (cas: 7528-78-1) 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. 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.Formula: C9H12N4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Poniatowski, Alexander J. et al. published their research in Synthesis in 2007 | CAS: 5351-07-5

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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. 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.COA of Formula: C11H13NO

Synthesis of the C1-C15 fragment of apicularen A through a regioselective electron-transfer-initiated cyclization reaction was written by Poniatowski, Alexander J.;Floreancig, Paul E.. And the article was included in Synthesis in 2007.COA of Formula: C11H13NO This article mentions the following:

In this paper we report the preparation of the benzyltetrahydropyran fragment I of the vacuolar ATPase inhibitor apicularen A through an oxidative cyclization protocol. In this reaction regioselective cleavage of one homobenzylic ether in the presence of another homobenzylic ether is achieved by selectively weakening one carbon-carbon σ-bond through substitution. This work demonstrates that oxidative fragmentation reactions can be used to generate stable cations selectively, even in the presence of other readily oxidized groups, provided that bond cleavage is sufficiently rapid following oxidation In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5COA of Formula: C11H13NO).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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. 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.COA of Formula: C11H13NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Tayebee, Reza et al. published their research in Journal of Molecular Catalysis A: Chemical in 2013 | CAS: 70291-62-2

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Product Details of 70291-62-2

Easy single-step preparation of ZnO nanoparticles by sedimentation method and studying their catalytic performance in the synthesis of 2-aminothiophenes via Gewald reaction was written by Tayebee, Reza;Javadi, Farzad;Argi, Gholamreza. And the article was included in Journal of Molecular Catalysis A: Chemical in 2013.Product Details of 70291-62-2 This article mentions the following:

Zinc oxide is a multi-purpose active material with important catalytic applications. Nano-sized ZnO particles were easily synthesized through sedimentation of zinc acetate di-hydrate in absolute ethanol and were characterized by XRD and SEM. The XRD results indicated pure wurtzite structure with the average particle size of 26.9 nm for the nano-particles. Size of ZnO nano-particles was decreased while solution concentration was increased. This observation would be explained considering enhancing nucleation processes of nano-particles at high concentration of zinc acetate. The prepared nano-particles (2.5 mol%) were used as catalyst for the fast and efficient synthesis of 2-aminothiophenes under solvent free conditions. The three-component mixture of a carbonyl compound, malonodinitrile, and elemental sulfur was converted into the corresponding 2-aminothiophene in moderate to high yields with excellent selectivity. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Product Details of 70291-62-2).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Product Details of 70291-62-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kaieda, Akira et al. published their research in ChemMedChem in 2019 | CAS: 60710-80-7

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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.Application In Synthesis of 3-Amino-4-methylbenzonitrile

Structure-Based Design, Synthesis, and Biological Evaluation of Imidazo[4,5-b]Pyridin-2-one-Based p38 MAP Kinase Inhibitors: Part 2 was written by Kaieda, Akira;Takahashi, Masashi;Fukuda, Hiromi;Okamoto, Rei;Morimoto, Shinji;Gotoh, Masayuki;Miyazaki, Takahiro;Hori, Yuri;Unno, Satoko;Kawamoto, Tomohiro;Tanaka, Toshimasa;Itono, Sachiko;Takagi, Terufumi;Sugimoto, Hiroshi;Okada, Kengo;Lane, Weston;Sang, Bi-Ching;Saikatendu, Kumar;Matsunaga, Shinichiro;Miwatashi, Seiji. And the article was included in ChemMedChem in 2019.Application In Synthesis of 3-Amino-4-methylbenzonitrile This article mentions the following:

We identified novel potent inhibitors of p38 mitogen-activated protein (MAP) kinase using a structure-based design strategy, beginning with lead compound, 3-(butan-2-yl)-6-(2,4-difluoroanilino)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1). To enhance the inhibitory activity of 1 against production of tumor necrosis factor-α (TNF-α) in human whole blood (hWB) cell assays, we designed and synthesized hybrid compounds in which the imidazo[4,5-b]pyridin-2-one core was successfully linked with the p-methylbenzamide fragment. Among the compounds evaluated, 3-(3-tert-butyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)-4-methyl-N-(1-methyl-1H-pyrazol-3-yl)benzamide (25) exhibited potent p38 inhibition, superior suppression of TNF-α production in hWB cells, and also significant in vivo efficacy in a rat model of collagen-induced arthritis (CIA). In this paper, we report the discovery of potent, selective, and orally bioavailable imidazo[4,5-b]pyridin-2-one-based p38 MAP kinase inhibitors. 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. 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.Application In Synthesis of 3-Amino-4-methylbenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

van Veldhoven, Jacobus P. D. et al. published their research in European Journal of Medicinal Chemistry in 2021 | CAS: 60979-25-1

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) 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. COA of Formula: C8H8N2O

Targeting the Kv11.1 (hERG) channel with allosteric modulators. Synthesis and biological evaluation of three novel series of LUF7346 derivatives was written by van Veldhoven, Jacobus P. D.;Campostrini, Giulia;van Gessel, Constantijn J. E.;Ward-van Oostwaard, Dorien;Liu, Rongfang;Mummery, Christine L.;Bellin, Milena;IJzerman, Adriaan P.. And the article was included in European Journal of Medicinal Chemistry in 2021.COA of Formula: C8H8N2O This article mentions the following:

Three novel series of substituted benzophenones for their allosteric modulation of the human Kv11.1 (hERG) channel were synthesized and evaluated. Effects of this is compared with reference compound LUF7346 previously shown to shorten the action potential of cardiomyocytes derived from human stem cells. Most compounds behaved as neg. allosteric modulators (NAMs) of [3H]dofetilide binding to the channel. Compound III [R = 2-Cl; R1 = CH2cPr; X= Y = C] was the most potent amongst all ligands, remarkably reducing the affinity of dofetilide in competitive displacement assays. One of the other II [R = H; X = N] tested in a second radioligand binding set-up, displayed unusual displacement characteristics with a pseudo-Hill coefficient significantly distinct from unity, further indicative of its allosteric effects on the channel. Some compounds were evaluated in a more physiol. relevant context in beating cardiomyocytes derived from human induced pluripotent stem cells. Surprisingly, the compounds tested showed effects quite different from the reference NAM LUF7346. For instance, compound I [R = 3-Me] prolonged, rather than shortened, the field potential duration, while it did not influence this parameter when the field potential was already prolonged by dofetilide. In subsequent patch clamp studies on HEK293 cells expressing the hERG channel the compounds behaved as channel blockers. In conclusion, new allosteric modulators of the hERG channel were successfully synthesized and identified . Unexpectedly, their effects differed from the reference compound in functional assays on hERG-HEK293 cells and human cardiomyocytes, to the extent that the compounds behaved as stand-alone channel blockers. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1COA of Formula: C8H8N2O).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) 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. COA of Formula: C8H8N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Esguerra, Kenneth Virgel N. et al. published their research in Angewandte Chemie, International Edition in 2014 | CAS: 5351-07-5

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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. 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: 5351-07-5

A biomimetic catalytic aerobic functionalization of phenols was written by Esguerra, Kenneth Virgel N.;Fall, Yacoub;Lumb, Jean-Philip. And the article was included in Angewandte Chemie, International Edition in 2014.HPLC of Formula: 5351-07-5 This article mentions the following:

A biomimetic approach that converts phenolic C-H bonds into C-O, C-N, and C-S bonds at the sole expense of reducing O2 to water (H2O) was reported. This method hinges on a regio- and chemoselective Cu-catalyzed aerobic oxygenation to provide orthoquinones. Orthoquinones are versatile intermediates, whose direct catalytic aerobic synthesis from phenols enables a mild and efficient means of synthesizing polyfunctional aromatic rings. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5HPLC of Formula: 5351-07-5).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) 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. 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: 5351-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Bhat, Radhika et al. published their research in IUCrData in 2020 | CAS: 60025-09-4

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Recommanded Product: 60025-09-4

4-Amino-6-(piperidin-1-yl)pyrimidine-5-carbonitrile was written by Bhat, Radhika;Shraddha, K. N.;Begum, Noor Shahina. And the article was included in IUCrData in 2020.Recommanded Product: 60025-09-4 This article mentions the following:

In the title compound, C10H13N5, the piperidine ring adopts a chair conformation with the exocyclic N-C bond in an axial orientation, and the dihedral angle between the mean planes of piperidine and pyrimidine rings is 49.57 (11)°. A short intramol. C-H···N contact generates an S(7) ring. In the crystal, N-H···N hydrogen bonds link the mols. into (100) sheets and a weak aromatic π-π stacking interaction is observed [centroid-centroid separation = 3.5559 (11) Å] between inversion-related pyrimidine rings. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Recommanded Product: 60025-09-4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Recommanded Product: 60025-09-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts