Month: January 2023

Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C-C, C-N, and C-O bond-forming cross-couplings was written by Kataoka, Noriyasu;Shelby, Quinetta;Stambuli, James P.;Hartwig, John F.. And the article was included in Journal of Organic Chemistry in 2002.Recommanded Product: 10282-32-3 This article mentions the following:

Pentaphenylferrocenyl di-tert-butylphosphine I (R = R¹ = Ph) was prepared; the scope of various cross-coupling processes catalyzed by palladium complexes of I has been investigated. I (R = R¹ = Ph) was prepared by lithiation of ferrocene followed by removal of solvent, addition of a 5:1 pentane:THF mixture, and addition of di(tert-butyl)chlorophosphine to give mono(di-tert-butylphosphino)ferrocene with high chemoselectivity; arylation of the ferrocenylphosphine with chlorobenzene as a solvent in the presence of palladium (II) acetate and sodium tert-butoxide yielded I in 40-65% yield overall. I (R = R¹ = Ph) acts as a highly effective ligand for palladium-catalyzed amination and for Suzuki coupling reactions with aryl- and alkylboronic acids. Unactivated, electron-rich, and electron-poor aryl bromides and chlorides undergo coupling reactions in the presence of palladium complexes of I (R = R¹ = Ph) with high turnover numbers Aryl bromides were coupled to alcs. in the presence of I (R = R¹ = Ph); silanols and electron-rich phenols were coupled to activated aryl halides in the presence of I (R = R¹ = Ph). Intramol. coupling reactions of alcs. and aryl bromides were successful, although substrates with hydrogens α to the alc. oxygen underwent some β-hydride elimination. Acyclic and cyclic primary and secondary alkyl- and arylamines underwent coupling reactions with aryl bromides and chlorides in the presence of I (R = R¹ = Ph). Aryl- and primary alkylboronic acids underwent coupling reactions in the presence of I (R = R¹ = Ph); coupling of alkylboronic acids with aryl halides was successful in the absence of toxic or expensive bases. Other substituted ferrocenylphosphines I (R = R¹ = 4-MeOC₆H₄, 4-F₃CC₆H₄) were prepared but palladium catalysts derived from the ligands showed little difference in catalytic activity when compared to palladium catalysts derived from I (R = R¹ = Ph). Palladium catalysts derived from I (R = R¹ = 3,5-Me₂C₆H₃) were active in coupling reactions with aryl halides and alcs. but not in amination or Suzuki coupling reactions; I (R = Ph; R¹ = H) acted as a catalyst for coupling reactions but gave significantly decreased yields due to decreased steric hindrance of the reaction center in the palladium complexes. I (R = R¹ = Ph) not only generates highly active palladium catalysts, but is also air stable both in solution and in the solid state. Palladium(0) complexes of I (R = R¹ = Ph) are air stable solids and react only slowly with oxygen in solution The crystal structures of I(R = R¹ = Ph; R = Ph, R¹ = H) were determined by x-ray crystallog. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Recommanded Product: 10282-32-3).

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.Recommanded Product: 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Structure-selectivity relationship in the chemoselective hydrogenation of unsaturated nitriles was written by Kukula, Pavel;Koprivova, Klara. And the article was included in Journal of Catalysis in 2005.Safety of 2-Cyclohexylacetonitrile This article mentions the following:

Several unsaturated nitriles of various structures (cinnamonitrile, cyclohex-1-enyl-acetonitrile, acrylonitrile, 3,3-dimethyl-acrylonitrile, geranylnitrile, and 2- and 3-pentenenitrile) with different substituents at the double bond were hydrogenated over Cr-doped Raney cobalt and nickel and over their undoped equivalent The substitution and the position of the double bond relative to the nitrile group are crucial in determining the chemoselectivity for the unsaturated amine. The double bond is not hydrogenated when it is sterically hindered or if it is too far from the nitrile group (cyclohex-1-enyl-acetonitrile, double bond at C-6 in geranylnitrile). In conjugated systems, such as acrylonitrile or 2-pentenylnitrile, the activated double bond is hydrogenated before the nitrile. An addnl. Me substituent at the double bond enhances the selectivity for unsaturated amines and, thus, 3,3-dimethyl-acrylonitrile and geranylnitrile were hydrogenated with selectivity up to 40%. The highest selectivities for unsaturated amines (up to 90%) were reached during the hydrogenation of nonconjugated systems, such as cyclohex-1-enyl-acetonitrile and 3-pentenylnitrile. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Safety of 2-Cyclohexylacetonitrile).

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Porous polymeric ligand promoted copper-catalyzed C-N coupling of (hetero)aryl chlorides under visible-light irradiation was written by Wang, Erfei;Chen, Kaixuan;Chen, Yinan;Zhang, Jiawei;Lin, Xinrong;Chen, Mao. And the article was included in Science China: Chemistry in 2021.Formula: C14H12N2 This article mentions the following:

A porous polymeric ligand (PPL) has been synthesized and complexed with copper to generate a heterogeneous catalyst (Cu@PPL) that has facilitated the efficient C-N coupling with various (hetero)aryl chlorides under mild conditions of visible-light irradiation at 80° (58 examples, up to 99% yields). This method could be applied to both aqueous ammonia and substituted amines, and is compatible to a variety of functional groups and heterocycles, as well as allows tandem C-N couplings with conjunctive dihalides. Furthermore, the heterogeneous characteristic of Cu@PPL has enabled a straightforward catalyst separation in multiple times of recycling with negligible catalytic efficiency loss by simple filtration, affording reaction mixtures containing less than 1 ppm of Cu residue. 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. 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 addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Formula: C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

CuI/Oxalic Diamide Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amines was written by Zhou, Wei;Fan, Mengyang;Yin, Junli;Jiang, Yongwen;Ma, Dawei. And the article was included in Journal of the American Chemical Society in 2015.Quality Control of 4-(Benzylamino)benzonitrile This article mentions the following:

A class of oxalic diamides are found to be effective ligands for promoting CuI-catalyzed aryl amination with less reactive (hetero)aryl chlorides. The reaction proceeds at 120 °C with K₃PO₄ as the base in DMSO to afford a wide range of (hetero)aryl amines in good to excellent yields. The bis(N-aryl) substituted oxalamides are superior ligands to N-aryl-N’-alkyl substituted or bis(N-alkyl) substituted oxalamides. Both the electronic nature and the steric property of the aromatic rings in ligands are important for their efficiency. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Quality Control of 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. 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.Quality Control of 4-(Benzylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Excited State Dipole Moments from an Efficient Analysis of Solvatochromic Stokes Shift Data was written by Mosurkal, Ravi;Samanta, A.;Radhakrishnan, T. P.. And the article was included in Journal of Physical Chemistry in 1994.Synthetic Route of C18H10N2 This article mentions the following:

It is shown that the solvatochromism of Stokes shifts has superior correlation with the solvent polarity function E_T^N, and the theor. basis for this is analyzed. The estimation of reliable excited state dipole moments from this correlation as well as the practical advantage of the method in terms of the possibility of employing mixed solvents is demonstrated. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Synthetic Route of C18H10N2).

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. 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 C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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,
Nitriles – Chemistry LibreTexts

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts