Tag: 100-200

In 2022,Yamada, Shigeyuki; Yoshida, Keigo; Sakurai, Tsuneaki; Hara, Mitsuo; Konno, Tustome published an article in Molecular Systems Design & Engineering. The title of the article was 《Effect of fluorine atoms in flexible chains on the phase transitions and photophysical behavior of D-π-A-type 4-alkoxy-4′-cyanodiphenylacetylene》.Application of 623-00-7 The author mentioned the following in the article:

D-π-A-type 4-alkoxy-4′-cyanodiphenylacetylenes bearing a decyloxy chain show a nematic liquid crystalline (LC) phase, whereas the incorporation of a semifluoroalkyl fragment results in a switch to the smectic A phase. The D-π-A-type π-conjugated mesogen exhibits photoluminescence, not only in solution and in the crystalline phase, but also in the mol. aggregated structure of the LC phase. In the experiment, the researchers used 4-Bromobenzonitrile(cas: 623-00-7Application of 623-00-7)

4-Bromobenzonitrile(cas: 623-00-7) is classified as organic nitriles, which are commonly use solvents and are reacted further for various applications such as manufacture of polymers and intermediates for pharmaceuticals and other organic chemicals,Application of 623-00-7 It can also be used as an aryl halide test compound in developing greener reaction conditions for Suzuki cross-coupling between aryl halides and phenyl boronic acid.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Tauber, Carolin; Wamser, Rebekka; Arkona, Christoph; Tuegend, Marisa; Abdul Aziz, Umer Bin; Pach, Szymon; Schulz, Robert; Jochmans, Dirk; Wolber, Gerhard; Neyts, Johan; Rademann, Joerg published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Chemical Evolution of Antivirals Against Enterovirus D68 through Protein-Templated Knoevenagel Reactions》.Name: 3-Oxo-3-phenylpropanenitrile The article contains the following contents:

The generation of bioactive mols. from inactive precursors is a crucial step in the chem. evolution of life, however, mechanistic insights into this aspect of abiogenesis are scarce. Here, we investigate the protein-catalyzed formation of antivirals by the 3C-protease of enterovirus D68. The enzyme induces aldol condensations yielding inhibitors with antiviral activity in cells. Kinetic and thermodn. analyses reveal that the bioactivity emerges from a dynamic reaction system including inhibitor formation, alkylation of the protein target by the inhibitors, and competitive addition of non-protein nucleophiles to the inhibitors. The most active antivirals are slowly reversible inhibitors with elongated target residence times. The study reveals first examples for the chem. evolution of bio-actives through protein-catalyzed, non-enzymic C-C couplings. The discovered mechanism works under physiol. conditions and might constitute a native process of drug development. In the experiment, the researchers used many compounds, for example, 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Name: 3-Oxo-3-phenylpropanenitrile)

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used to produce 2-benzoyl-3-furan-2-yl-acrylonitrile. It is an active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines.Name: 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Journal of Asian Natural Products Research included an article by Zhang, Juan; Li, Jia-Cheng; Song, Jia-Li; Cheng, Zhi-Qiang; Sun, Ji-Zheng; Jiang, Cheng-Shi. COA of Formula: C8H6BrN. The article was titled 《Synthesis and evaluation of coumarin/1,2,4-oxadiazole hybrids as selective BChE inhibitors with neuroprotective activity》. The information in the text is summarized as follows:

A series of new coumarin/1,2,4-oxadiazole hybrids were synthesized and evaluated for cholinesterase inhibitory and neuroprotective activities. Among them, enantiomers and showed potent hBChE inhibitory activity with IC50 values of 8.17 and 9.56 μM, resp., and also exhibited good selectivity for hBChE over hAChE by 9.49- and 7.58-fold, resp. In addition, both compounds could protect SH-SY5Y cells against Aβ25-35-induced neurotoxicity. The preliminary bioassay results provided a new chemotype for multifunctional anti-Alzheimer′s disease agents and continuing investigation into compounds and is warranted. In the experiment, the researchers used 4-Cyanobenzyl bromide(cas: 17201-43-3COA of Formula: C8H6BrN)

4-Cyanobenzyl bromide(cas: 17201-43-3) is used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile. It is also useful in the preparation of 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile by reaction with 2H-tetrazole in the presence of potassium hydroxide.COA of Formula: C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2008,Norris, Timothy; Leeman, Kyle published 《Development of a New Variant of the Migita Reaction for Carbon-Sulfur Bond Formation Used in the Manufacture of Tetrahydro-4-[3-[4-(2-methyl-1H-imidazol-1-yl)phenyl]thio]phenyl-2H-pyran-4-carboxamide》.Organic Process Research & Development published the findings.HPLC of Formula: 31938-07-5 The information in the text is summarized as follows:

Palladium-catalyzed carbon-sulfur bond formation using modified Migita reaction conditions was explored and applied to the synthesis of a former antiasthma drug candidate, tetrahydro-4-[3-[4-(2-methyl-1H-imidazol-1-yl)phenyl]thio]phenyl-2H-pyran-4-carboxamide (1). The reaction was developed into a general method for thioaryl halide cross-coupling, and a specific example of its use to synthesize a key intermediate, tetrahydro-4-[3-(4-fluorophenyl)thio]phenyl-2H-pyran-4-carboxamide was demonstrated at large scale to provide phase II clin. supplies of 1. Comparison of the multistep phase I process and the two-step phase II process showed an overall yield advantage over the bond-forming steps from common starting material to active pharmaceutical ingredient API 1 of 40%. The ligand effect in the modified Migita reaction is described in detail. The second step of the scale-up process illustrated formation of carbon-nitrogen bonds without use of palladium catalysis, providing a contrast to the first reaction; both reactions were developed into efficient single-vessel direct isolation processes. The experimental process involved the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5HPLC of Formula: 31938-07-5)

2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands or 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione.HPLC of Formula: 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wu, Wenliang; Su, Weiping published their research in Journal of the American Chemical Society on August 10 ,2011. The article was titled 《Mild and Selective Ru-Catalyzed Formylation and Fe-Catalyzed Acylation of Free (N-H) Indoles Using Anilines as the Carbonyl Source》.Electric Literature of C10H6N2O The article contains the following contents:

Indoles undergo regioselective formylation and acylation reactions with N-methylaniline or N-benzylanilines in the presence of either ruthenium(III) or iron(II) chlorides using tert-Bu hydroperoxide as the oxidant to give 3-formyl or 3-benzoylindoles in 34-86% yields. The processes are operationally simple and compatible with a variety of functional groups. Reaction of indole with N-(13C-methyl)aniline yields 3-(13C-formyl)indole in 70% yield, unambiguously establishing that the carbonyl carbon in the formylation products originates from the Me group of N-Me aniline. In the experiment, the researchers used 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Electric Literature of C10H6N2O)

3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Electric Literature of C10H6N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Water elimination rate measurements for tertiary-butanol》 were Heyne, J.; Dooley, S.; Dryer, F.. And the article was published in Chemical and Physical Processes in Combustion in 2011. Product Details of 658-98-0 The author mentioned the following in the article:

Alternatives to petroleum derived transportation fuels, particularly C4 alcs. (butanols), have been investigated increasingly over the last three years. One butanol isomer, teritary-butanol (derived from petroleum), is already used com. as a gasoline octane number enhancer. Studies of tertiary-butanol (t-butanol) combustion suggest that the water elimination channel (C4H9OH = iC4H8 + H2O) can contribute to approx. 75% of t-butanol consumption in flames [1]. A study of this key reaction has recently been performed in the Princeton Variable Pressure Flow Reactor (VPFR) using radical trappers to isolate this path in t-butanol pyrolysis experiments Radical trappers consume radicals produced in the pyrolysis sufficiently fast to preclude significant secondary radical reactions with t-butanol. Numerical experiments were conducted to estimate the appropriate radical trapper (1,3,5-trimethylbenzene) to fuel (t-butanol) molar ratios. The water elimination reaction was then studied in the temperature range of 658-980 K at 6.1 atm. The rate determination of water elimination reaction of t-butanol at each temperature was found by using a global least squares fit considering the species of water and isobutene. The resulting rates are then compared to previous exptl., computational and estimated rate currently in the literature. Anal. suggests that the water elimination reaction is faster than estimated from previous exptl. studies and occurs at a rate in good agreement with some more recent rate estimations [2].3-Chloro-4-fluorophenylacetonitrile(cas: 658-98-0Product Details of 658-98-0) was used in this study.

3-Chloro-4-fluorophenylacetonitrile(cas: 658-98-0) belongs to nitriles. Nitriles are found in many useful compounds. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.Product Details of 658-98-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Luo, Ling; Liu, Dan; Lan, Shichao; Gan, Xiuhai published an article in Frontiers in Chemistry (Lausanne, Switzerland). The title of the article was 《Design, synthesis and biological activity of novel chalcone derivatives containing an 1,2,4-oxadiazole moiety》.Category: nitriles-buliding-blocks The author mentioned the following in the article:

To discover a lead compound for agricultural use, 34 novel chalcone derivatives I [R1 = H, 4-MeO, 2,4-di-Cl, etc; R2 = H, 4-Me, 4-F, 4-Cl] and II [R1 = H, 4-Me, 4-MeO, 2-Cl, 2,4-di-Cl; R2 = H, 4-Me, 4-F, 4-Cl] containing an 1,2,4-oxadiazole moiety were designed and synthesized. Their nematocidal activities against Bursaphelenchus xylophilus, Aphelenchoides besseyi and Ditylenchus dipsaci and their antiviral activities against tobacco mosaic virus (TMV), pepper mild mottle virus (PMMoV) and tomato spotted wilt virus (TSWV) were evaluated. Biol. assay results indicated that compounds I [R1 = 3-MeO, 4-MeO, R2 = H] showed good nematocidal activities against B. xylophilus, A. besseyi and D. dipsaci, with LC50 values of 35.5, 44.7 and 30.2μg/mL and 31.8, 47.4 and 36.5μg/mL, resp., which are better than tioxazafen, fosthiazate and abamectin. Furthermore, compound I [R1 = 2-MeO, R2 = H] demonstrated excellent protective activity against TMV, PMMoV and TSWV, with EC50 values of 210.4, 156.2 and 178.2μg/mL, resp., which are superior to ningnanmycin (242.6, 218.4 and 180.5μg/mL). In the experimental materials used by the author, we found 4-Fluorobenzonitrile(cas: 1194-02-1Category: nitriles-buliding-blocks)

4-Fluorobenzonitrile(cas: 1194-02-1) is used in the synthesis of flurenones, pharmaceutical prerequisites, as well as opiod receptor antagonists.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Lan, Chunling Blue; Auclair, Karine published their research in European Journal of Organic Chemistry in 2021. The article was titled 《Ammonium Chloride-Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation》.Application of 1194-02-1 The article contains the following contents:

Ammonium chloride promoted the reaction between amines and potassium cyanate to generate monosubstituted ureas in water. This method proceeded rapidly under microwave irradiation and tolerates a broad range of functional groups. Unlike previous strategies, it was compatible with other nucleophiles, acid-labile moieties and most of the common protecting groups. The products precipitate out of solution, allowing facile isolation without column chromatog. In addition to this study using 4-Fluorobenzonitrile, there are many other studies that have used 4-Fluorobenzonitrile(cas: 1194-02-1Application of 1194-02-1) was used in this study.

4-Fluorobenzonitrile(cas: 1194-02-1) is used in the synthesis of flurenones, pharmaceutical prerequisites, as well as opiod receptor antagonists.Application of 1194-02-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Organic Process Research & Development included an article by Perkins, Robert J.; Hughes, Alexander J.; Weix, Daniel J.; Hansen, Eric C.. Reference of 4-Bromobenzonitrile. The article was titled 《Metal-Reductant-Free Electrochemical Nickel-Catalyzed Couplings of Aryl and Alkyl Bromides in Acetonitrile》. The information in the text is summarized as follows:

While reductive cross-electrochem. coupling is an attractive approach for the synthesis of complex mols. at both small and large scale, two barriers for large-scale applications have remained: the use of stoichiometric metal reductants and a need for amide solvents. In this communication, new conditions that address these challenges are reported. The nickel-catalyzed reductive cross-coupling of aryl bromides with alkyl bromides can be conducted in a divided electrochem. cell using acetonitrile as the solvent and diisopropylamine as the sacrificial reductant to afford coupling products in synthetically useful yields (22-80%). Addnl., the use of a combination of the ligands 4,4′,4”-tri-tert-butyl-2,2′:6′,2′-terpyridine and 4,4′-di-tert-butyl-2,2′-bipyridine is essential to achieve high yields. In the experiment, the researchers used many compounds, for example, 4-Bromobenzonitrile(cas: 623-00-7Reference of 4-Bromobenzonitrile)

4-Bromobenzonitrile(cas: 623-00-7) is classified as organic nitriles, which are commonly use solvents and are reacted further for various applications such as manufacture of polymers and intermediates for pharmaceuticals and other organic chemicals,Reference of 4-Bromobenzonitrile It can also be used as an aryl halide test compound in developing greener reaction conditions for Suzuki cross-coupling between aryl halides and phenyl boronic acid.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2013,Vogt, Matthias; Nerush, Alexander; Iron, Mark A.; Leitus, Gregory; Diskin-Posner, Yael; Shimon, Linda J. W.; Ben-David, Yehoshoa; Milstein, David published 《Activation of Nitriles by Metal Ligand Cooperation. Reversible Formation of Ketimido- and Enamido-Rhenium PNP Pincer Complexes and Relevance to Catalytic Design》.Journal of the American Chemical Society published the findings.Reference of 2-(3-Bromophenyl)acetonitrile The information in the text is summarized as follows:

The dearomatized complex cis-[Re-(PNPtBu*)-(CO)2] (4) undergoes cooperative activation of CN triple bonds of nitriles via [1,3]-addition Reversible C-C and Re-N bond formation in 4 was investigated in a combined exptl. and computational study. The reversible formation of the ketimido complexes (5-7) was observed When nitriles bearing an alpha methylene group are used, reversible formation of the enamido complexes (8 and 9) takes place. The reversibility of the activation of the nitriles in the resulting ketimido compounds was demonstrated by the displacement of p-CF3-benzonitrile from cis-[Re-(PNPtBu-N=CPhpCF3)-(CO)2] (6) upon addition of an excess of benzonitrile and by the temperature-dependent [1,3]-addition of pivalonitrile to complex 4. The reversible binding of the nitrile in the enamido compound cis-[Re-(PNPtBu-HNC=CHPh)-(CO)2] (9) was demonstrated via the displacement of benzyl cyanide from 9 by CO. Computational studies suggest a stepwise activation of the nitriles by 4, with remarkably low activation barriers, involving precoordination of the nitrile group to the Re-(I) center. The enamido complex 9 reacts via β-carbon methylation to give the primary imino complex cis-[Re-(PNPtBu-HN=CC-(Me)-Ph)-(CO)2]-OTf 11. Upon deprotonation of 11 and subsequent addition of benzyl cyanide, complex 9 is regenerated and the monomethylation product 2-phenylpropanenitrile is released. Complexes 4 and 9 were found to catalyze the Michael addition of benzyl cyanide derivatives to α,β-unsaturated esters and carbonyls. In addition to this study using 2-(3-Bromophenyl)acetonitrile, there are many other studies that have used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Reference of 2-(3-Bromophenyl)acetonitrile) was used in this study.

According to other reports, 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) is used in the preparation of diarylpyrimidines (DAPYs) as HIV-1 non-nucleoside reverse transcriptase inhibitors.Reference of 2-(3-Bromophenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts