Author: Jessica.F

Borrowing Hydrogen Methodology for N-Benzylation using a π-Benzylpalladium System in Water was written by Hikawa, Hidemasa;Koike, Toshitaka;Izumi, Kyoko;Kikkawa, Shoko;Azumaya, Isao. And the article was included in Advanced Synthesis & Catalysis in 2016.Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile This article mentions the following:

The authors demonstrate a borrowing hydrogen methodol. using the unique reactivity of the π-benzylpalladium system in water, which offers an efficient and environmentally friendly N-monobenzylation of electron-deficient anilines or 2-aminopyridine with non-activated benzylic alcs. under neutral conditions. The crossover experiment using benzyl-α,α-d₂ alc. and 3-methylbenzyl alc. afforded H/D scrambling products, suggesting that the borrowing hydrogen pathway occurred in the authors’ catalytic system. The authors’ simple protocol can accomplish a gram scale reaction of 2-aminobenzonitrile (76% isolated yield), and was performed using only 1 mol % Pd(OAc)₂ and 2 mol % TPPMS without other additives in water. 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. 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.Quality Control of 2-Amino-4-(trifluoromethyl)benzonitrile

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Synthesis and antiprotozoal activity of cationic 1,4-diphenyl-1H-1,2,3-triazoles. [Erratum to document cited in CA152:074962] was written by Bakunov, Stanislav A.;Bakunova, Svetlana M.;Wenzler, Tanja;Ghebru, Maedot;Werbovetz, Karl A.;Brun, Reto;Tidwell, Richard R.. And the article was included in Journal of Medicinal Chemistry in 2011.Application In Synthesis of 3-Amino-4-methoxybenzonitrile This article mentions the following:

On page 270, in the left column, the Acknowledgment section was incomplete, and should read: “This work was supported by The Bill and Melinda Gates Foundation and NIH Grant 5U01AI075641.”. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Application In Synthesis of 3-Amino-4-methoxybenzonitrile).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) 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 In Synthesis of 3-Amino-4-methoxybenzonitrile

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Nitrile – Wikipedia,
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Targeting the K_v11.1 (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.HPLC of Formula: 60710-80-7 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-methylbenzonitrile (cas: 60710-80-7HPLC of Formula: 60710-80-7).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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: 60710-80-7

Referemce:
Nitrile – Wikipedia,
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Mononuclear half-sandwich iridium and rhodium complexes through C-H activation: Synthesis, characterization and catalytic activity was written by Yao, Zi-Jian;Li, Kuan;Li, Peng;Deng, Wei. And the article was included in Journal of Organometallic Chemistry in 2017.HPLC of Formula: 10282-32-3 This article mentions the following:

A series of mononuclear half-sandwich cyclometalated group 9 (Ir and Rh) metal complexes were synthesized in good yields through metal-mediated C-H bond activation. These air-stable C, N-chelate mode complexes have similar solid state structures. Both exptl. results and DFT calculations confirmed that no binuclear complexes were generated in this reaction. The iridium complex 3a exhibited good catalytic activity for the reduction of both electron-rich and electron-poor aryl imines with low catalyst loading in the presence of formic acid/triethylamine (F/T) azeotropic mixture All complexes were fully characterized by elemental anal. and IR and NMR spectroscopies. The structures were further confirmed by single-crystal X-ray anal. 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. 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. 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: 10282-32-3

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Nitrile – Wikipedia,
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Selective cyclooxygenase-2 inhibitors: heteroaryl modified 1,2-diarylimidazoles are potent, orally active antiinflammatory agents was written by Khanna, Ish K.;Yu, Yi;Huff, Renee M.;Weier, Richard M.;Xu, Xiangdong;Koszyk, Francis J.;Collins, Paul W.;Cogburn, J. Nita;Isakson, Peter C.;Koboldt, Carol M.;Masferrer, Jaime L.;Perkins, William E.;Seibert, Karen;Veenhuizen, Amy W.;Yuan, Jinhua;Yang, Dai-Chang;Zhang, Yan Y.. And the article was included in Journal of Medicinal Chemistry in 2000.Name: 3-Methylthiophene-2-carbonitrile This article mentions the following:

A series of heteroaryl modified 1,2-diarylimidazoles has been synthesized and found to be potent and highly selective (1000-9000-fold) inhibitors of the human COX-2. 3-Pyridyl-derived COX-2 selective inhibitor I exhibited excellent activity in acute (carrageenan induced paw edema, ED₅₀ = 5.4 mg/kg) and chronic (adjuvant induced arthritis, ED₅₀ = 0.25 mg/kg) models of inflammation. The relatively long half-life of I in rat and dog prompted investigation of the pyridyl and other heteroaromatic systems containing potential metabolic functionalities. A number of substituted pyridyl and thiazole containing compounds. e.g., II, demonstrated excellent oral activity in every efficacy model evaluated. Several orally active diarylimidazoles exhibited desirable pharmacokinetics profiles and showed no GI toxicity in the rat up to 100 mg/kg in both acute and chronic models. The paper describes facile and practical syntheses of the targeted diarylimidazoles. The structure-activity relationships and antiinflammatory properties of a series of diarylimidazoles are discussed. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Name: 3-Methylthiophene-2-carbonitrile).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) 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. 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.Name: 3-Methylthiophene-2-carbonitrile

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Efficient Access to 2,6,8-Trisubstituted 4-Aminoquinazolines through Microwave-Assisted One-Pot Chemoselective Tris-Suzuki-Miyaura or S_NAr/Bis-Suzuki-Miyaura Reactions in Water was written by Kabri, Youssef;Crozet, Maxime D.;Terme, Thierry;Vanelle, Patrice. And the article was included in European Journal of Organic Chemistry in 2015.Application In Synthesis of 2-Amino-3,5-dibromobenzonitrile This article mentions the following:

An efficient, sequential, one-pot strategy for synthesizing polyfunctionalized quinazoline derivatives is presented. After selective amination of 6,8-dibromo-2,4-dichloroquinazoline at the C-4 position, 2,6,8-trisubstituted 4-aminoquinazoline derivatives I (R = 4-MeOC₆H₄, 4-ClC₆H₄, pyridin-3-yl, etc.) were prepared through one-pot chemoselective sequential tris-Suzuki-Miyaura or S_NAr/bis-Suzuki-Miyaura reactions under microwave irradiation in an aqueous medium. This approach, used with a variety of boronic acids, affords polysubstituted quinazoline derivatives in good to excellent yields in only a few steps and in the environmentally benign solvent water. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Application In Synthesis of 2-Amino-3,5-dibromobenzonitrile).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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. 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. Application In Synthesis of 2-Amino-3,5-dibromobenzonitrile

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Cytochrome P450 Catalyzed Oxidative Hydroxylation of Achiral Organic Compounds with Simultaneous Creation of Two Chirality Centers in a Single C-H Activation Step was written by Roiban, Gheorghe-Doru;Agudo, Ruben;Reetz, Manfred T.. And the article was included in Angewandte Chemie, International Edition in 2014.Reference of 24056-34-6 This article mentions the following:

Regio- and stereoselective oxidative hydroxylation of achiral or chiral organic compounds mediated by synthetic reagents, catalysts, or enzymes generally leads to the formation of one new chiral center that appears in the resp. enantiomeric or diastereomeric alcs. By contrast, when subjecting appropriate achiral compounds to this type of C-H activation, the simultaneous creation of two chiral centers with a defined relative and absolute configuration may result, provided that control of the regio-, diastereo-, and enantioselectivity is ensured. The present study demonstrates that such control is possible by using wild-type (wt) or mutant forms of the monooxygenase cytochrome P 450 BM3 as catalysts in the oxidative hydroxylation of methylcyclohexane and seven other monosubstituted cyclohexane derivatives In the experiment, the researchers used many compounds, for example, 4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6Reference of 24056-34-6).

4-Hydroxycyclohexanecarbonitrile (cas: 24056-34-6) 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.Reference of 24056-34-6

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Electrochemical oxidation of acylsilanes and their tosylhydrazones was written by Yoshida, Junichi;Itoh, Masanori;Matsunaga, Shinichiro;Isoe, Sachihiko. And the article was included in Journal of Organic Chemistry in 1992.Recommanded Product: 2-Cyclohexylacetonitrile This article mentions the following:

Oxidation potentials of acylsilanes were much less pos. than those of ketones and aldehydes. The effect of silicon is attributed to the rise of the HOMO level by the interaction between the C-Si σ orbital and the nonbonding p orbital of the carbonyl oxygen which in turn favors the electron transfer. Preparative electrochem. oxidation of acylsilanes proceeded smoothly, giving rise to facile cleavage of the C-Si bond and the introduction of nucleophiles such as alcs., water, and carbamates onto the carbonyl carbon. Electrochem. properties of tosylhydrazones of acylsilanes were also investigated. A decrease in oxidation potential of tosylhydrazones caused by silyl substitution was smaller than that for carbonyl compounds Preparative electrochem. oxidation of tosylhydrazones of acylsilanes gave the corresponding nitriles with consumption of a catalytic amount of electricity. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Recommanded Product: 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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 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.Recommanded Product: 2-Cyclohexylacetonitrile

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Nitrile – Wikipedia,
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Synthesis, photophysical characterization and DFT studies on fluorine-free deep-blue emitting Pt(II) complexes was written by Sanning, Jan;Stegemann, Linda;Nyenhuis, Marvin;Daniliuc, Constantin G.;Doltsinis, Nikos L.;Strassert, Cristian A.. And the article was included in Zeitschrift fuer Naturforschung, B: A Journal of Chemical Sciences in 2016.Synthetic Route of C7H6N2O This article mentions the following:

Herein authors show that cyclometalated, square planar Pt(II) complexes can be tuned to achieve deep-blue phosphorescent emitters. For this purpose, the introduction of an electron-donating moiety on two different bidentate NN and NO fluorine-free luminophores, namely 2-(1H-tetrazol-5-yl)pyridine and picolinic acid, was carried out. The remaining two coordination sites of the Pt(II) metal center were filled by a sterically demanding cyclometallating unit, namely a tertiary phosphite CP ligand. This ancillary ligand avoids aggregation and provides high solubility in organic solvents. Based on this approach, we were able to blue-shift the emission of the complexes down to 411 nm, and to achieve a maximal photoluminescence quantum yield of 56% in the solid state. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Synthetic Route of C7H6N2O).

4-methoxypicolinonitrile (cas: 36057-44-0) 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. 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.Synthetic Route of C7H6N2O

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A facile, choline chloride/urea catalyzed solid phase synthesis of coumarins via Knoevenagel condensation was written by Harishkumar, Hosanagara N.;Mahadevan, Kittappa M.;Kiran Kumar, Hittalumane C.;Satyanarayan, Nayak D.. And the article was included in Organic Communications in 2011.Related Products of 51473-74-6 This article mentions the following:

The influence of choline chloride/urea ionic liquid in solid phase on the Knoevenagel condensation is demonstrated. The active methylene compounds such as meldrum acid, diethylmalonate, Et cyanoacetate, dimethylmalonate, were efficiently condensed with various salicylaldehydes in presence of choline chloride/urea ionic liquid without using any solvents or addnl. catalyst. The reaction is remarkably facile because of the air and water stability of the catalyst, and needs no special precautions. The reactions were completed within 1 h with excellent yields (95%). The products formed were sufficiently pure, and can be easily recovered. The use of ionic liquid choline chloride/urea in solid phase offered several significant advantages such as low cost, greater selectivity and easy isolation of products. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Related Products of 51473-74-6).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts