Tag: 100-200

A strategy of two-step tandem catalysis towards direct N-alkylation of nitroarenes with ethanol via facile fabricated novel Co-based catalysts derived from coordination polymers was written by Wang, Jing;Qi, Tianqinji;Li, Zhibin;She, Wei;Li, Xuewei;Li, Jingfang;Yan, Pengfei;Li, Weizuo;Li, Guangming. And the article was included in Journal of Catalysis in 2019.Computed Properties of C9H10N2 This article mentions the following:

Three novel N-doped carbon supported Co/Co₃O₄ catalysts, namely, Co@CN-hmta, Co@CN-larg and Co-Co₃O₄@CN-bipy, with sheet-, worm-, honeycomb-like morphologies resp., have been fabricated by the pyrolysis of well-defined coordination polymers (CPs). Base upon the application of as-prepared catalysts, for the reaction of N-alkylation of nitroarenes 4-RC₆H₄NO₂ (R = H, 3-Cl, 4-Me, etc.) with ethanol, a direct two-step tandem reaction is realized, in which Co@CN-hmta delivers 100% conversion/selectivity of N-ethylaniline/N,N-diethylaniline from the direct N-alkylation of nitroarenes with ethanol. The kinetic studies were conducted to confirm that the N-alkylation of aniline with ethanol is the rate-determining step in the two-step tandem reaction. The SEM/EDX, XRD, Raman, TEM, XPS, and CO₂-TPD characterization results have revealed that sizes and dispersion of metallic Co, amount of structural defects and surface Lewis basicity towards three catalysts can be tuned by changing the structures of Co-based CPs designed by different organic linkers, which may also help to understand the preparation of industrial catalysts on a mol. level. The optimized Co@CN-hmta catalyst is easily recycled by using the external magnet for successive reuses without any loss in both activity and selectivity. This is the first reported carbon-nitrogen species supported Co/Co₃O₄ catalysts derived from the CPs, which could effectively catalyze the N-alkylation of nitroarenes with ethanol to produce the secondary amines and/or tertiary amines. This low-cost, recyclable and easy scale-up N-doped carbon supported catalyst may be of potential application in various heterogeneous catalytic reactions. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0Computed Properties of C9H10N2).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) 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. 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. Computed Properties of C9H10N2

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Fragment-Based Approach to the Development of an Orally Bioavailable Lactam Inhibitor of Lipoprotein-Associated Phospholipase A2 (Lp-PLA₂) was written by Woolford, Alison J.-A.;Day, Philip J.;Beneton, Veronique;Berdini, Valerio;Coyle, Joseph E.;Dudit, Yann;Grondin, Pascal;Huet, Pascal;Lee, Lydia Y. W.;Manas, Eric S.;McMenamin, Rachel L.;Murray, Christopher W.;Page, Lee W.;Patel, Vipulkumar K.;Potvain, Florent;Rich, Sharna J.;Sang, Yingxia;Somers, Don O.;Trottet, Lionel;Wan, Zehong;Zhang, Xiaomin. And the article was included in Journal of Medicinal Chemistry in 2016.Related Products of 104798-53-0 This article mentions the following:

Lp-PLA₂ has been explored as a target for a number of inflammation associated diseases, including cardiovascular disease and dementia. This article describes the discovery of a new fragment derived chemotype that interacts with the active site of Lp-PLA₂. The starting fragment hit was discovered through an x-ray fragment screen and showed no activity in the bioassay (IC₅₀ > 1 mM). The fragment hit was optimized using a variety of structure-based drug design techniques, including virtual screening, fragment merging, and improvement of shape complementarity. A novel series of Lp-PLA₂ inhibitors was generated with low lipophilicity and a promising pharmacokinetic profile. In the experiment, the researchers used many compounds, for example, 2-Fluoro-5-hydroxybenzenecarbonitrile (cas: 104798-53-0Related Products of 104798-53-0).

2-Fluoro-5-hydroxybenzenecarbonitrile (cas: 104798-53-0) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Related Products of 104798-53-0

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Reaction of substituted benzenes and chloral. VII. Reaction of ο-acetotoluidide and chloral was written by Yasue, Masaichi;Takai, Yoshiharu;Yoshizawa, Shigeru. And the article was included in Yakugaku Zasshi in 1957.HPLC of Formula: 60710-80-7 This article mentions the following:

O-Acetotoluidide (30 g.), 33 g. CCl₃CH(OH)₂, and 100 ml. concentrated H₂SO₄ heated 20 hrs. at 50-60°, the product poured over ice, let stand overnight, the precipitate filtered off, washed with H₂O, refluxed with 700 ml. H₂O, cooled, the precipitate filtered off, and extracted with C₆H₆ gave 12 g. C₆H₆-soluble portion (I) and a small amount of C₆H₆-insoluble portion (II); the above reaction 3 weeks at 10-15° yielded 6.7 g. I and 13.5 g. II (this yielded 0.5 g. substance, m. 158-65°); the reaction 10 days at 20° yielded 13 g. I and 3.5 g. II. I (12 g.) in 80 ml. AcOH treated portionwise with 15 g. Zn, heated 4 hrs. on an H₂O bath, the solution filtered while hot, the filtrate neutralized with NH₄OH, the solution concentrated in vacuo, and the residue extracted with C₆H₆ gave 2.1 g. 2,5-Me(Cl₂CHCH₂)C₆H₃NHAc (III), needles, m. 155.5-6° (EtOH). III (1.7 g.) in 30 ml. EtOH and 0.5 g. NaOH in 10 ml. EtOH refluxed 1 hr., the EtOH removed by heating with 1 g. NH₄Cl and 2 ml. H₂O, and the residue extracted with C₆H₆ gave 1.2 g. 2,5-Me(ClCH:CH)C₆H₃NHAc (IV), needles, m. 173-3.5° (EtOH). IV (0.9 g.) in 50 ml. Me₂CO treated dropwise with 1.5 g. KMnO₄ in 40 ml. H₂O, let stand 2 hrs., the solution decolorized with Na₂SO₃ and concentrated, the residue acidified with 10% H₂SO₄, and the product recrystallized from EtOH gave 4,3-Me(AcNH)C₆H₃CO₂H (V), needles, m. 277°. II (13 g.), 80 ml. AcOH, and 15 g. Zn was heated 4 hrs.; the product in a small amount of EtOH gave 0.1 g. insoluble [4,3-Me(AcNH)C₆H₃]₂C₂H₄, needles, m. 298°, and the filtrate gave III, m. 156°. 4,3-Me(O₂N)C₆H₃CN (10 g.), 25 g. Sn, and 100 ml. EtOH at 25-45° treated with 70 ml. concentrated H₂SO₄, heated until a clear solution was obtained, the EtOH removed, the residue made alk. with NaOH, and extracted with Et₂O gave 8 g. 4,3-Me(H₂N)C₆H₃CN (VI), m. 76-8°. VI (8 g.) and 15 ml. Ac₂O refluxed 1 hr. and the product diluted with 100 ml. H₂O gave 10 g. 4,3-Me(AcNH)C₆H₃CN (VII), m. 153-4° (EtOH). VII (8 g.), 150 ml. EtOH, 50 ml. 30% H₂O₂, and 4 ml. 10% NaOH let stand overnight, the EtOH removed, and the residue recrystallized from H₂O gave 6 g. 4,3-Me(AcNH)C₆H₃CONH₂ (VIII), columns, m. 185-7°. VIII (4 g.) and 50 ml. concentrated H₂SO₄ at 0° treated portionwise with 2.5 g. NaNO₂, let stand 1 hr. at room temperature, the precipitate filtered off, taken up in 10% Na₂CO₃, the solution filtered, the filtrate acidified with 10% H₂SO₄, and the product recrystallized from 50% EtOH gave 2.5 g. V, needles, m. 278°. V (0.5 g.), 5 ml. AcOH, 5 ml. concentrated HCl, and 2.5 ml. H₂O heated 30 min. on an H₂O bath, the product made alk. with NH₄OH, evaporated to dryness, and the residue recrystallized from H₂O gave 4,3-Me(H₂N)C₆H₃CO₂H, columns, m. 164°. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7HPLC of Formula: 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. 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.HPLC of Formula: 60710-80-7

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An Old Story in the Parallel Synthesis World: An Approach to Hydantoin Libraries was written by Bogolubsky, Andrey V.;Moroz, Yurii S.;Savych, Olena;Pipko, Sergey;Konovets, Angelika;Platonov, Maxim O.;Vasylchenko, Oleksandr V.;Hurmach, Vasyl V.;Grygorenko, Oleksandr O.. And the article was included in ACS Combinatorial Science in 2018.Quality Control of 3-Amino-4-methylbenzonitrile This article mentions the following:

An approach to the parallel synthesis of hydantoin libraries by reaction of in situ generated 2,2,2-trifluoroethylcarbamates and α-amino esters was developed. To demonstrate utility of the method, a library of 1158 hydantoins designed according to the lead-likeness criteria (MW 200-350, cLogP 1-3) was prepared The success rate of the method was analyzed as a function of physicochem. parameters of the products, and it was found that the method can be considered as a tool for lead-oriented synthesis. A hydantoin-bearing submicromolar primary hit acting as an Aurora kinase A inhibitor was discovered with a combination of rational design, parallel synthesis using the procedures developed, in silico and in vitro screenings. 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. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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

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Co-Monomer Control of Carbon Nitride Semiconductors to Optimize Hydrogen Evolution with Visible Light was written by Zhang, Jinshui;Zhang, Guigang;Chen, Xiufang;Lin, Sen;Moehlmann, Lennart;Dolega, Grzegorz;Lipner, Grzegorz;Antonietti, Markus;Blechert, Siegfried;Wang, Xinchen. And the article was included in Angewandte Chemie, International Edition in 2012.Product Details of 55406-13-8 This article mentions the following:

Herein, we advance a strategy by employing a variety of new monomer building blocks with the desired compositions and electronic structures for chem. incorporation into the conjugated polymeric network of g-C₃N₄. Most precursors of carbon nitride polymers contain cyano groups, amino groups, or both, with the simplest case being cyanamide, which can undergo multiple thermal condensations to form stable aromatic carbon nitrides based on tri-s-triazine subunits. Therefore, we synthesized organic mols. bearing amino and/or cyano functionalities to integrate them directly into the carbon nitride polymers. This design may allow ample choice of organic anchoring groups, being a potentially valuable way to alter the phys. and chem. properties of the resulting heterogeneous organo-catalysts. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Product Details of 55406-13-8).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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. 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.Product Details of 55406-13-8

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Direct one-step conversion of alcohols into nitriles was written by Davis, Roman;Untch, Karl G.. And the article was included in Journal of Organic Chemistry in 1981.Reference of 4435-14-7 This article mentions the following:

Primary, secondary, and tertiary alcs. (10 compounds) are converted into the corresponding nitriles by treatment with two equivalent of NaCN-Me₃SiCl and a catalytic amount of NaI in DMF-CH₃CN. The reactions are complete in 2-8 h. Except for cyclohexanol, the yields range from 75-98%. Evidence is presented which demonstrates that S_N2 and S_N1 processes are obtained and a common bis-silyloxonium intermediate is suggested. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Reference of 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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. 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.Reference of 4435-14-7

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Application of electrogenerated triphenylmethyl anion as a base for alkylation of arylacetic esters and arylacetonitriles and isomerization of allylbenzenes was written by Suzuki, Shohei;Kato, Mitsuko;Nakajima, Shoichi. And the article was included in Canadian Journal of Chemistry in 1994.Application In Synthesis of 2-(4-Methoxyphenyl)-2-methylpropanenitrile This article mentions the following:

Phenylacetic esters and phenylacetonitriles were alkylated with alkyl halides, at the position α to an ester or nitrile, either at room temperature (20°) or at -78°, by making use of electrogenerated triphenylmethyl anion (trityl anion). For example, regioselective alkylation of benzeneacetates gave α-alkylbenzeneacetates I (X = H, MeO; R¹ = alkyl; R² = Me, Et). Double-bond isomerization of allylbenzenes was also effectively accomplished using this electrogenerated base (EGB). In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Application In Synthesis of 2-(4-Methoxyphenyl)-2-methylpropanenitrile).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. 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 In Synthesis of 2-(4-Methoxyphenyl)-2-methylpropanenitrile

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Optical activity in βγ-unsaturated ketones. Part 2. Effect of the magnitude and energy of the electric transition dipole moment in the aromatic groups in 1- and 1,5-substituted 9,10-ethano-9,10-dihydroanthracen-11-one derivatives was written by Hagishita, Sanji;Kuriyama, Kaoru. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1978.COA of Formula: C11H11N This article mentions the following:

Optically active dihydroanthracene derivatives I (e.g., Z = H₂, O; R = CO₂H, R¹ = H; R = R¹ = CONH₂) were prepared from the Diels-Alder adduct of II (R = H, CO₂Me) and CH₂:C(OAc)CN. Alteration of the substituents of I changed the magnitude of the transition dipole moment and the transition energy in the aromatic chromophore, and the optical activity depended on the transition dipole-moment magnitude. In the experiment, the researchers used many compounds, for example, 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0COA of Formula: C11H11N).

5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0) 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. 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: C11H11N

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Antituberculous compounds. XXII. Monoalkylaminobenzothioamides was written by Kakimoto, Shichiro;Tone, Ikuko. And the article was included in Journal of Medicinal Chemistry in 1965.Safety of 4-(Ethylamino)benzonitrile This article mentions the following:

Several monoalkyl, phenyl, and benzyl derivatives of 4-aminobenzothioamide, and their precursor nitriles were prepared to test the hypothesis that the extinction coefficient, Ε_maximum of the C-N stretching vibration in the ir adsorption spectrum of the parent nitrile parallels the inhibitory action against Mycobacterium tuberculosis strain H37Rv in vitro. No conclusions were drawn. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0Safety of 4-(Ethylamino)benzonitrile).

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.Safety of 4-(Ethylamino)benzonitrile

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First Gewald reaction ignited by sodium polysulfide: greener ultrasound-promoted synthesis of substituted 2-aminothiophenes in the absence of catalyst was written by Liang, Chengyuan;Lei, Dong;Wang, Xiuzhen;Zhang, Qingqing;Yao, Qizheng. And the article was included in Journal of Sulfur Chemistry in 2013.Name: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

In this paper, a modified and facile Gewald reaction triggered by sodium polysulfide in the absence of catalytic base was developed. This approach involves a one-pot ultrasound-irritated aqueous reaction between ketones or aldehydes, malononitrile and sodium sulfide [Na₂(S_x)] [sodium polysulfide, sodium sulfide [Na₂(S₄)], sodium sulfide [Na₂(S₆)], sodium sulfide (NaS)]. which are converted into the corresponding 2-aminothiophene derivatives in moderate to high yields. In comparison with conventional methods, the prominent features of this ultrasound-mediated procedure are exptl. simplicity, good functional group tolerance, atom efficiency, and the use of water as a green solvent. The title compounds thus formed included and amine nitrile [2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile] (I) and an analog, 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (II), 2-amino-4-ethyl-3-thiophenecarbonitrile, 2-amino-4-(phenylmethyl)-3-thiophenecarbonitrile. The synthesis of the target compounds was achieved using cyclohexanone, cyclopentanone, butanal, propanal, hexanal, benzeneacetaldehyde, benzenepropanal as starting materials. 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Name: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts