Tag: 200-300

A novel three-component reaction of triphenylphosphine, DMAD, and electron-deficient styrenes: facile synthesis of cyclopentenyl phosphoranes was written by Nair, Vijay;Deepthi, Ani;Beneesh, P. B.;Eringathodi, Suresh. And the article was included in Synthesis in 2006.Quality Control of 2-(Anthracen-9-ylmethylene)malononitrile This article mentions the following:

The zwitterion formed from triphenylphosphine and DMAD (di-Me acetylenedicarboxylate) adds to electron-deficient styrenes to form stable cyclopentenyl phosphoranes in 23% to 80% yield. This is the first example of such a zwitterion in which the phosphine is incorporated into the addition product. A mechanism for the reaction is proposed. The mol. structure of the formed cyclopentenyl phosphorane (I) was determined by x-ray crystallog. This cyclopentenyl phosphorane did not undergo Wittig reaction with 4-nitrobenzaldehyde. The cyclopentenyl phosphoranes thus formed can be oxidized to cyclopentene 1,2-diones. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Quality Control of 2-(Anthracen-9-ylmethylene)malononitrile).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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.Quality Control of 2-(Anthracen-9-ylmethylene)malononitrile

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Synthesis of Carbamoyl Fluorides Using a Difluorophosgene Surrogate Derived from Difluorocarbene and Pyridine N-Oxides was written by Cadwallader, Dusty;Tiburcio, Tristan R.;Cieszynski, George A.;Le, Christine M.. And the article was included in Journal of Organic Chemistry in 2022.Name: 4-(Benzylamino)benzonitrile This article mentions the following:

The authors report a method for the synthesis of carbamoyl fluorides from secondary amines using bench-stable, inexpensive, and readily accessible starting materials that, when combined, yield a surrogate for toxic difluorophosgene (COF₂) gas. In contrast to state-of-the-art methods for the synthesis of carbamoyl fluorides, the current protocol does not require the use of pre-functionalized substrates, the preparation of light-, temperature-, and/or moisture-sensitive chems., nor the application of explosive fluorinating reagents. 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. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Name: 4-(Benzylamino)benzonitrile

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Nitrile – Wikipedia,
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A novel thiocarbamide functionalized graphene oxide supported bimetallic monodisperse Rh-Pt nanoparticles (RhPt/TC@GO NPs) for Knoevenagel condensation of aryl aldehydes together with malononitrile was written by Sen, Betul;Akdere, Esma Hazal;Savk, Aysun;Gultekin, Emine;Parali, Ozge;Goksu, Haydar;Sen, Fatih. And the article was included in Applied Catalysis, B: Environmental in 2018.Reference of 55490-87-4 This article mentions the following:

It is shown in this study that the graphene oxide can be mainly functionalized with a single species of sulfur and can be reduced to form a graphene which is functionalized with monothiol at the same time. By the help of thiocarbamide-functionalized graphene oxide (TC@GO) the monodisperse rhodium/platinum nanoparticles (RhPt/TC@GO NPs) have been synthesized as promising catalysts for the Knoevenagel condensation to benzylidenemalononitrile derivatives of aryl aldehydes. The monodisperse RhPt/TC@GO NPs have been prepared via a facile method. The novel thiocarbamide-functionalized graphene oxide (TC@GO) supported rhodium/platinum nanoparticles (RhPt/TC@GO NPs) are identified by characterization techniques such as the Raman spectroscopy, high resolution transmission electron microscopy (HRTEM), transmission electron microscopy (TEM), X-ray diffraction (XRD) and XPS. The spectroscopic and morphol. studies of the monodisperse RhPt/TNM@GO NPs indicate the highly crystalline form, well dispersity, ultrafine structure and colloidally stable NPs. After fully characterization of prepared nanoparticles, the novel nanocatalysts have been tried for the Knoevenagel condensation to benzylidenemalononitrile derivatives of aryl aldehydes and show excellent catalytic activity and a yield over 99% by the reaction at room temperature within 8-35 min in the presence of malononitrile and derivatives of aldehyde. As a result, the prepared nanocomposites exhibit very good heterogeneous catalyst properties for Knoevenagel condensation reactions. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Reference of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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 55490-87-4

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Nitrile – Wikipedia,
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Amination of benzylic C-H bonds by arylazides catalyzed by Co^II-porphyrin complexes: A synthetic and mechanistic study was written by Ragaini, Fabio;Penoni, Andrea;Gallo, Emma;Tollari, Stefano;Li Gotti, Claudia;Lapadula, Marta;Mangioni, Enrica;Cenini, Sergio. And the article was included in Chemistry – A European Journal in 2003.Computed Properties of C14H12N2 This article mentions the following:

Co^II-porphyrin complexes catalyze the reaction of aromatic azides (ArN₃) with hydrocarbons that contain a benzylic group (ArR¹R²CH) to give the corresponding amines (ArR¹R²C-N-HAr). When at least one of the R substituents is hydrogen, the catalytic reaction proceeds further to give the imine ArRC:NAr in good yields. The reaction mechanism has been investigated. The reaction proceeds through a reversible coordination of the arylazide to the Co^II-porphyrin complex. This unstable adduct can either react with the hydrocarbon in the rate-determining step or decompose by a unimol. mechanism to afford a putative “nitrene” complex, which reacts with more azide, but not with the hydrocarbon, to afford the byproduct diaryldiazene. The kinetics of the catalytic reaction have been investigated for a range of azides and substituted toluenes. Aryl azides with electron-withdrawing substituents react at a faster rate and a good correlation is found between the log(k) and the Taft parameters. On the other hand, an excellent correlation between the logarithm of the rate for substituted toluenes relative to that of toluene and a radical parameter (σ_JJ) alone was found, with no significant contribution by polar parameters. An explanation has been proposed for this anomalous effect and for the very high isotopic effect (k_H/k_D = 14) found. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Computed Properties of C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile carbon shifts are in the range of 115�25 ppm whereas in isonitriles the shifts are around 155�65 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.Computed Properties of C14H12N2

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Nitrile – Wikipedia,
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Design, synthesis and biological evaluation of new series of hexahydroquinoline and fused quinoline derivatives as potent inhibitors of wild-type EGFR and mutant EGFR (L858R and T790M) was written by Shaheen, Mennatallah A.;El-Emam, Ali A.;El-Gohary, Nadia S.. And the article was included in Bioorganic Chemistry in 2020.Product Details of 55490-87-4 This article mentions the following:

New series of hexahydroquinoline and fused quinoline derivatives were designed and synthesized. The thirty seven new compounds were screened for in vitro antitumor activity against HepG2, HCT-116 and MCF-7 cancer cells. Results indicated that certain compounds, including I, have the strongest potency against the three cancer cells, and they were further screened for in vitro cytotoxicity against A431 and H1975 cancer cells, as well as WI38 and WISH normal cells. Results revealed that I potently inhibited the growth of H1975 cells harboring EGFR^T790M mutation (IC₅₀ = 1.32 ± 0.2μM) over A431 cells overexpressing EGFR^WT (IC₅₀ = 4.96 ± 0.3μM). Moreover, the seven compounds displayed low cytotoxicity against the tested normal cells. The seven potent antitumor compounds were examined for their ability to inhibit the activity of EGFR^WT. The attained data manifested that I has remarkable EGFR^WT inhibitory activity (IC₅₀ = 0.083 ± 0.002μM) compared to erlotinib (IC₅₀ = 0.067 ± 0.002μM). Compound I was further studied for its enzymic inhibitory activity against other eight human kinases, and it displayed outstanding inhibitory activity against EGFR^L858R and EGFR^T790M mutants (IC₅₀ = 0.053 ± 0.002, 0.026 ± 0.001μM, resp.), as well as JAK3 (IC₅₀ = 0.069 ± 0.003μM). Anal. of cell cycle evidenced that I induces cell cycle arrest in G2/M and pre-G1 phases in the tested cancer cells. In addition, cancer cell death induced by I was proved to take place via apoptosis supported by elevated Bax/Bcl-2 ratio in the tested cancer cells. Moreover, docking results confirmed the good binding interactions of I with EGFR^WT, EGFR^L858R, EGFR^T790M and JAK3, which came in agreement with the results of in vitro enzyme assay. Further, I is predicted to have good oral absorption, good drug-likeness properties and low toxicity risks in human. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Product Details of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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. 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 55490-87-4

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Nitrile – Wikipedia,
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Palladium-catalyzed amination of aryl bromides using temperature-controlled microwave heating was written by Wan, Yiqian;Alterman, Mathias;Hallberg, Anders. And the article was included in Synthesis in 2002.HPLC of Formula: 10282-32-3 This article mentions the following:

Fast Pd-catalyzed aminations of aryl bromides were conducted in a non-inert reaction medium with temperature-controlled microwave heating. With a reaction time of 4 min at 130° or 180°, both electron-rich and electron-deficient aryl bromides reacted with various amines to provide fair to good yields of the corresponding secondary and tertiary anilines. As an example the amination of 4-bromobenzonitrile with imidazole is presented. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3HPLC of Formula: 10282-32-3).

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. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.HPLC of Formula: 10282-32-3

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Nitrile – Wikipedia,
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A simple route to N-(2-hydroxyarylidene)nitroanilines, versatile synthons for coumarins was written by Czerney, P.;Hartmann, H.. And the article was included in Journal fuer Praktische Chemie (Leipzig) in 1982.Application of 51473-74-6 This article mentions the following:

RCH:NC₆H₄NO₂ (R = 4-amino-2-hydroxyphenyl, 1-hydroxy-2-naphthyl, 2-hydroxy-1-naphthyl) were prepared by treating the phenols with HC(OEt)₃ and H₂NC₆H₄NO₂. RCH:NC₆H₄NO₂ form B complexes and cyclized with R¹CH₂CO₂Et or R¹CH₂CN (R¹ = Ac, cyano, COCH₂CO₂Et, CONH₂, 2-benzimidazolyl, 4-O₂NC₆H₄, 4-phenyl-2-thiazolyl) to give the coumarins I (R² = H, R³ = 7-NMe₂, 7-pyrrolidino, 7-piperidino, 7-NEt₂; R²R³ = 5,6-CH:CHCH:CH, 7,8-CH:CHCH:CH). In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Application of 51473-74-6).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) 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).Application of 51473-74-6

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Characterization of intramolecular charge-transfer transitions: 2,2-dicyanovinylaromatics was written by Aihara, Junichi;Araya, Kotaro;Chiba, Kazuhiko;Matsunaga, Yoshio. And the article was included in Advances in Molecular Relaxation and Interaction Processes in 1980.Related Products of 55490-87-4 This article mentions the following:

The 1st electronic transition energies of 2,2-dicyanovinylaroms. are linearly related to vertical ionization potentials of the parent aromatics As in the case of binary charge-transfer complexes, this relationship gives a definite exptl. support to the charge-transfer character of the electronic transitions concerned. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Related Products of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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. 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.Related Products of 55490-87-4

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp³)-H Borylation of Cyclopropanes was written by Shi, Yongjia;Gao, Qian;Xu, Senmiao. And the article was included in Journal of the American Chemical Society in 2019.COA of Formula: C8H5BrFN This article mentions the following:

The authors herein report an Ir-catalyzed enantioselective C(sp³)-H borylation of cyclopropanecarboxamides using a chiral bidentate boryl ligand for the 1st time. A variety of substrates with α-quaternary C centers could be compatible in this reaction to provide β-borylated products with good to excellent enantioselectivities. Also the borylated products can be used as versatile precursors engaging in stereospecific transformations of C-B bonds, including the synthesis of a bioactive compound Levomilnacipran. In the experiment, the researchers used many compounds, for example, 2-(3-Bromo-4-fluorophenyl)acetonitrile (cas: 501420-63-9COA of Formula: C8H5BrFN).

2-(3-Bromo-4-fluorophenyl)acetonitrile (cas: 501420-63-9) 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. 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: C8H5BrFN

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Nitrile – Wikipedia,
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Ruthenium(II) bis(hydrazone) complexes derived from 1,3,4-oxadiazoles: Synthesis, crystal structure and catalytic application in N-alkylation reactions was written by Prakash, Govindan;Ramachandran, Rangasamy;Nirmala, Muthukumaran;Viswanathamurthi, Periasamy;Sanmartin, Jesus. And the article was included in Inorganica Chimica Acta in 2015.Electric Literature of C14H12N2 This article mentions the following:

1,3,4-Oxadiazoles (A-C) were derived via a series of reactions between isoniazid and salicylaldehydes. While reacting the oxadiazoles with [RuHCl(CO)(PPh₃)₃] in the presence of NaOH, mononuclear ruthenium(II) complexes bearing ‘salen’ type N,N’-bis(salicylidene)hydrazone ligands (1–3) were obtained. The oxadiazoles and ruthenium(II) complexes were characterized by anal. and spectral methods. The single crystal XRD analyses of complexes 1 and 2 suggested an octahedral geometry around ruthenium(II) ions in which the bis(hydrazone) act as mononeg. bidentate ligands. Also the presence of an intramol. hydrogen bonding between the hydroxyl proton and one of the azomethine nitrogens in all the complexes. Further, the complexes were proved as versatile catalysts for the N-alkylation of amines with alcs. under optimized reaction conditions. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Electric Literature of C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Electric Literature of C14H12N2

Referemce:
Nitrile – Wikipedia,
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