Tag: 100-200

《Three-Component Olefin Dicarbofunctionalization Enabled by Nickel/Photoredox Dual Catalysis》 was written by Campbell, Mark W.; Compton, Jordan S.; Kelly, Christopher B.; Molander, Gary A.. Quality Control of 4-BromobenzonitrileThis research focused onvinylboronate preparation three component dicarbofunctionalization aryl bromide alkyltrifluoroborate; bisborylated verbenone derivative preparation crystal structure; mol structure bisborylated verbenone derivative; nickel catalyzed three component dicarbofunctionalization aryl bromide alkyltrifluoroborate vinylboronate; photoredox dual catalyst nickel three component dicarbofunctionalization vinylboronate. The article conveys some information:

An intermol., photocatalytic dicarbofunctionalization (DCF) of olefins enabled by the merger of Giese-type addition with Ni/photoredox dual catalysis was realized. Capitalizing on the rapid addition of 3° radicals to alkenes and their reluctance toward single electron metalation to Ni complexes, regioselective alkylation and arylation of olefins is possible. This dual catalytic method not only permits elaborate species to be assembled from commodity materials, but also allows quaternary and tertiary centers to be installed in a singular, chemoselective olefin difunctionalization. This multicomponent process occurs under exceptionally mild conditions, compatible with a diverse range of functional groups and synthetic handles such as pinacolboronate esters. This technol. was directly applied to the synthesis of an intermediate to a preclin. candidate (TK-666) and its derivatives In the part of experimental materials, we found many familiar compounds, such as 4-Bromobenzonitrile(cas: 623-00-7Quality Control of 4-Bromobenzonitrile)

4-Bromobenzonitrile(cas: 623-00-7) has been used in the synthesis of 4-iodobenzonitrile via photo-induced aromatic Finkelstein iodination reaction.Quality Control 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

《The Dual Role of Benzophenone in Visible-Light/Nickel Photoredox-Catalyzed C-H Arylations: Hydrogen-Atom Transfer and Energy Transfer》 was written by Dewanji, Abhishek; Krach, Patricia E.; Rueping, Magnus. Application of 623-00-7This research focused ontoluene halobenzene nickel photoredox catalysis arylation; diphenylmethane preparation; C−H functionalization; atom transfer; benzophenone; energy transfer; metallaphotoredox. The article conveys some information:

A dual catalytic protocol for the direct arylation of non-activated C(sp3)-H bonds was developed. Upon photochem. excitation, the excited triplet state of a diaryl ketone photosensitizer abstracts a hydrogen atom from an aliphatic C-H bond. This inherent reactivity was exploited for the generation of benzylic radicals which subsequently enter a nickel catalytic cycle, accomplishing the benzylic arylation.4-Bromobenzonitrile(cas: 623-00-7Application of 623-00-7) was used in this study.

4-Bromobenzonitrile(cas: 623-00-7) has been used in the synthesis of 4-iodobenzonitrile via photo-induced aromatic Finkelstein iodination reaction.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

《Exploration of highly efficient blue-violet light conversion agents for an agricultural film based on structure optimization of triphenylacrylonitrile》 was written by Wang, Yongtao; Yu, Yongjiang; Liu, Wenjing; Ren, Litong; Ge, Guixian. Category: nitriles-buliding-blocksThis research focused ontriarylacrylonitrile agricultural doping film light conversion; acrylonitrile derivatives; fluorescence; light conversion agents; light conversion film; photosynthesis. The article conveys some information:

To obtain highly efficient blue-violet light conversion agents used for an agricultural film, six triarylacrylonitrile derivatives and their doping films were prepared Further, the luminogens have the ability to convert UV light into blue-violet light and exhibit aggregation-dependent fluorescence emission and high-contrast fluorescence quantum yields from 0.004 to 0.833. On the basis of X-ray single-crystal diffraction anal. and aggregation-induced emission activity tests, the variant fluorescence quantum yields are attributed to intermol. π-π stacking and phase transition between the crystalline state and amorphous state. In a simulated greenhouse environment, the luminogens exhibit excellent photostability. However, their fluorescence intensity drops to 17-40% of the prime intensity after outdoor radiation for 1 mo as a result of the ring-closing oxidation reaction (in the summer). By comprehensively considering the above photophys. properties and mech. properties of the doping film, 2-([1,1′-biphenyl]-4-yl)-3,3-diphenylacrylonitrile is a potential light conversion agent for an agricultural film in the winter. More importantly, the results indicate that the properties of the light conversion films are expected to be further improved by mol. design, inhibiting the ring-closing oxidation reaction and dispersion of crystalline nanoparticles in the doping film. In the experimental materials used by the author, we found 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Category: nitriles-buliding-blocks)

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.Category: nitriles-buliding-blocks

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Nitrile – Wikipedia,
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SDS of cas: 614-16-4In 2021 ,《Mechanistic selectivity investigation and 2D-QSAR study of some new antiproliferative pyrazoles and pyrazolopyridines as potential CDK2 inhibitors》 appeared in European Journal of Medicinal Chemistry. The author of the article were Hassan, Ghaneya S.; Georgey, Hanan H.; Mohammed, Esraa Z.; George, Riham F.; Mahmoud, Walaa R.; Omar, Farghaly A.. The article conveys some information:

Novel series of diphenyl-1H-pyrazoles (Z/E)I (Ar = C6H5, 4-BrC6H4, 2-thienyl, etc.) and pyrazolo[3,4-b]pyridines II and III (R = H, OMe, Cl; X = CH2, O, NCH3) were synthesized and evaluated for their antiproliferative activity against breast cancer cell line (MCF7) and Hepatocellular carcinoma cell line (HepG2). The highest MCF7 growth inhibition activity was attained via compounds (Z/E)I (Ar = 4-CH3OC6H4) and III (R = OMe; X = O) (IC50 = 1.29 and 0.93μM, resp.), while compounds II (4-FC6H4) and III (R = OMe; X = NMe) were the most active ones against HepG2 (IC50 = 1.57 and 1.33μM, resp.) compared to doxorubicin (IC50 = 1.88 and 7.30μM, resp.). Cell cycle anal. showed arrest at S and G2-M phases in MCF7 cells treated with (Z/E)I (Ar = 4-CH3OC6H4) and III (R = OMe; X = O), and at G2-M and G1/S phases in HepG2 cells treated with II (4-FC6H4) and III (R = OMe; X = NMe), resp. Apoptotic effect of compounds (Z/E)I (Ar = 4-CH3OC6H4), II (4-FC6H4), III (R = OMe; X = O, NMe) was indicated via their pre-G1 early and late apoptotic effects and augmented levels of caspase-9/MCF7 and caspase-3/HepG2. A worthy safety profile was assessed for compounds (Z/E)I (Ar = 4-CH3OC6H4) and III (R = OMe; X = O) on MCF10A and compounds II (4-FC6H4) and III (R = OMe; X = NMe) on THLE2 treated normal cells. Furthermore, compounds (Z/E)I (Ar = 4-CH3OC6H4), II (4-FC6H4) and III (R = OMe; X = NMe) displayed a promising selective profile for CDK2 inhibition vs. CDK1, CDK4, and CDK7 isoforms are proved from their selectivity index. Docking in CDK2 ATP binding site, co-crystallized with R-Roscovitine, demonstrated analogous interactions and comparable binding energy with the native ligand. 2D QSAR sighted the possible structural features governing the CDK2 inhibition activity elicited by the studied pyrazolo[3,4-b]pyridines II and III. These findings present compounds (Z/E)I (Ar = 4-CH3OC6H4), II (4-FC6H4) and III (R = OMe; X = NMe) as selective CDK2 inhibitors with promising antiproliferative activity against MCF7 and HepG2 cancer cells.3-Oxo-3-phenylpropanenitrile(cas: 614-16-4SDS of cas: 614-16-4) was used in this study.

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used in the synthesis of substituted naphtho[1,8-bc]pyrans. It was also used as building block in the preparation of 4H-pyrans, 2-pyridones, furans and carbocyclics.SDS of cas: 614-16-4

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Traxler, Michael; Gisbertz, Sebastian; Pachfule, Pradip; Schmidt, Johannes; Roeser, Jerome; Reischauer, Susanne; Rabeah, Jabor; Pieber, Bartholomaus; Thomas, Arne published an article in 2022. The article was titled 《Acridine-Functionalized Covalent Organic Frameworks (COFs) as Photocatalysts for Metallaphotocatalytic C-N Cross-Coupling》, and you may find the article in Angewandte Chemie, International Edition.Formula: C7H4BrN The information in the text is summarized as follows:

Covalent organic frameworks (COFs) are structurally tuneable, porous and crystalline polymers constructed through the covalent attachment of small organic building blocks as elementary units. Using the myriad of such building blocks, a broad spectrum of functionalities has been applied for COF syntheses for broad applications, including heterogeneous catalysis. Herein, we report the synthesis of a new family of porous and crystalline COFs using a novel acridine linker and benzene-1,3,5-tricarbaldehyde derivatives bearing a variable number of hydroxy groups. With the broad absorption in the visible light region, the COFs were applied as photocatalysts in metallaphotocatalytic C-N cross-coupling. The fully β-ketoenamine linked COF showed the highest activity, due to the increased charge separation upon irradiation The COF showed good to excellent yields for several aryl bromides, good recyclability and even catalyzed the organic transformation in presence of green light as energy source. The results came from multiple reactions, including the reaction of 2-Bromobenzonitrile(cas: 2042-37-7Formula: C7H4BrN)

2-Bromobenzonitrile(cas: 2042-37-7) is a precursor to the quinazolinones, a class of drugs used to treat autoimmune diseases and coronary heart disease. In addition, 2-bromobenzonitrile can be used for the Suzuki coupling reaction.Formula: C7H4BrN

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ghadermazi, Mohammad; Molaei, Somayeh; Ghadermazi, Nahid published an article in 2021. The article was titled 《Introduction of Fe into mesoporous MCM-41 for the synthesis of 5-substituted 1H-Tetrazoles from aryl nitriles in water》, and you may find the article in Microporous and Mesoporous Materials.Safety of 2-Bromobenzonitrile The information in the text is summarized as follows:

In this exploration, new recyclable mesoporous-supported iron particles with the ligand and without ligand (MCM-41@ 3,4,5-tri hydroxyphenyl acetic acid @Fe and MCM-41@Fe) have been developed through post-functionalization modification of silica MCM-41. These catalysts were demonstrated to be novel, effective, and green for the synthesis of 5-substituted 1H-tetrazoles from aryl nitriles in water. In these systems, 5-substituted 1H-tetrazoles are produced as the only product. Fe3+ species were identified as active sites. The ordered mesoporous iron-silica catalyst with the ligand displayed better catalytic activity compared to iron-silica catalyst without the ligand, which was ascribed to the improvement of the inter-action of iron with the support. The catalysts can be easily separated using simple recovery and reused several times with consistent activity. After reading the article, we found that the author used 2-Bromobenzonitrile(cas: 2042-37-7Safety of 2-Bromobenzonitrile)

2-Bromobenzonitrile(cas: 2042-37-7) is used as a starting material to synthesize novel benzothiophene derivatives that were found to exhibit antibacterial and antifungal activity. It is commonly employed in reactions that require an electron-rich species to carry out nucleophilic substitution (or addition) reactions.Safety of 2-Bromobenzonitrile

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Dreas, Agnieszka; Kucwaj-Brysz, Katarzyna; Pyziak, Karolina; Kulesza, Urszula; Wincza, Ewelina; Fabritius, Charles-Henry; Michalik, Kinga; Gabor-Worwa, Ewelina; Golas, Aniela; Milik, Mariusz; Masiejczyk, Magdalena; Majewska, Eliza; Pysniak, Kazimiera; Wojcik-Trechcinska, Urszula; Sandowska-Markiewicz, Zuzanna; Brzozka, Krzysztof; Ostrowski, Jerzy; Rzymski, Tomasz; Mikula, Michal published an article in 2021. The article was titled 《Discovery of indazole-pyridinone derivatives as a novel class of potent and selective MNK1/2 kinase inhibitors that protecting against endotoxin-induced septic shock》, and you may find the article in European Journal of Medicinal Chemistry.Formula: C8H6BrN The information in the text is summarized as follows:

The mitogen-activated protein kinase (MAPK)-interacting kinases 1 and 2 (MNKs 1/2) and their downstream target eIF4E, play a role in oncogenic transformation, progression and metastasis. These results provided rationale for development of first MNKs inhibitors, currently in clin. trials for cancer treatment. Inhibitors of the MNKs/eIF4E pathway are also proposed as treatment strategy for inflammatory conditions. Here we present results of optimization of indazole-pyridinone derived MNK1/2 inhibitors among which compounds I and II, selective and metabolically stable derivatives Both compounds decreased levels of eIF4E Ser206 phosphorylation (pSer209-eIF4E) in MOLM16 cell line. When administered in mice compounds I and II significantly improved survival rates of animals in the endotoxin LD challenge model, with concomitant reduction of proinflammatory cytokine levels – TNFα and IL-6 in serum. Identified MNK1/2 inhibitors represent a novel class of immunomodulatory compounds with a potential for the treatment of inflammatory diseases including sepsis. The results came from multiple reactions, including the reaction of 4-Cyanobenzyl bromide(cas: 17201-43-3Formula: C8H6BrN)

4-Cyanobenzyl bromide(cas: 17201-43-3) is an important intermediate for pharmaceutical production. It can be used for the synthesis of a series of piperidine-linked aromatic diimidazolines, which have been synthesized as conformationally restricted congeners of the anti-Pneumocystis carinii (PCP) drug, Pentamidine.Formula: C8H6BrN

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Sathiyan, Govindasamy; Mathivanan, Dhamodiran; Bhuvaneshwari, Balasubramaniam; Garg, Ashish; Gupta, Raju Kumar; Singh, Anand published an article in 2021. The article was titled 《Olefin-linked conjugated fluorescent oligomer: Design, synthesis, photophysical studies and detection of nitroaromatic compounds (NACs) in aqueous media》, and you may find the article in Sensors and Actuators, A: Physical.Safety of 4-Cyanobenzyl bromide The information in the text is summarized as follows:

The development of novel fluorescent polymers has attracted significant attention owing to their potential applications in energy and environmental sciences. This study reports novel oligomer (TRZBT) synthesis via Wittig-Horner reaction using bithiophene aldehyde and triazine tri-Et phosphite. The resulting oligomer possesses large porous morphol., which was confirmed using SEM anal. Further, the chem. structure of TRZBT was confirmed by FT-IR, NMR, and GPC studies. The triazine acceptor (A) unit linked with bithiophene donor (D) unit through olefin π-conjugation resulted in a Donor-π-Acceptor (D-π-A) type oligomer. Detailed studies of the solvent-dependent photophys. properties of TRZBT were performed. Due to the alternate D-A structure of oligomer, enhanced intramol. charge transfer (ICT) properties between D and A moiety was observed Further, TRZBT in THF and THF: H2O (10:90) system effectively detected nitro-explosives in aqueous media, which exhibited high sensitivity, selectivity, and quick response via fluorescence quenching. TRZBT showed a higher quenching constant (Ksv) value of 4.91 x 105 M-1 towards picric acid as compared with other nitroaroms. Significantly, the detection limit of 1.58 nM in a 100% aqueous medium confirms that the synthesized material can detect even trace levels of the analyte. The experimental part of the paper was very detailed, including the reaction process of 4-Cyanobenzyl bromide(cas: 17201-43-3Safety of 4-Cyanobenzyl bromide)

4-Cyanobenzyl bromide(cas: 17201-43-3) is a white solid. Its melting point is 113-117°C, and flash point is 125.1°C. It is insoluble in water at 20°C. It is stable under normal temperatures and pressures. It should be stored at 0-5°C.Safety of 4-Cyanobenzyl bromide

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Nitrile – Wikipedia,
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El-serwy, Walaa s.; El-serwy, Weam s.; Mohamed, Neama a.; Kassem, Emad m. m.; Mostafa, Rasha e.; Mohamed, Hanaa s. published their research in Russian Journal of Bioorganic Chemistry in 2021. The article was titled 《Synthesis, Biological Evaluation, Molecular Docking, ADME Predictions and QSAR Studies of Novel 1,2-Diazet and Pyrrole Derivatives as Anti-Inflammatory Agents》.Category: nitriles-buliding-blocks The article contains the following contents:

Here we synthesized novel 1, 2-diazet and pyrrole derivatives and screened for their anti-inflammatory activity. In vivo anti-inflammatory evaluation results revealed that compounds (XVI), (XIV) and (XI) exhibited the highest anti-inflammatory potencies all over the 4 h, while compounds (VII), (V) and (XV) exhibited the lowest potencies when compared to indomethacin group. Mol. docking study was used to predict the binding mode towards c-Jun N-Terminal Kinase. In addition, ADME (absorption, distribution, metabolism, and excretion) prediction and QSAR (quant. structure-activity relationship) study of compounds was carried out resp. The experimental process involved the reaction of 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Category: nitriles-buliding-blocks)

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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Mechanistic Analysis of Metallaphotoredox C-N Coupling: Photocatalysis Initiates and Perpetuates Ni(I)/Ni(III) Coupling Activity》 was written by Till, Nicholas A.; Tian, Lei; Dong, Zhe; Scholes, Gregory D.; MacMillan, David W. C.. Electric Literature of C7H4BrN And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

The combined use of reaction kinetic anal., ultrafast spectroscopy, and stoichiometric organometallic studies has enabled the elucidation of the mechanistic underpinnings to a photocatalytic C-N cross-coupling reaction. Steady-state and ultrafast spectroscopic techniques were used to track the excited-state evolution of the employed iridium photocatalyst, determine the resting states of both iridium and nickel catalysts, and uncover the photochem. mechanism for reductive activation of the nickel cocatalyst. Stoichiometric organometallic studies along with a comprehensive kinetic study of the reaction, including rate-driving force anal., unveiled the crucial role of photocatalysis in both initiating and sustaining a Ni(I)/Ni(III) cross-coupling mechanism. The insights gleaned from this study further enabled the discovery of a new photocatalyst providing a >30-fold rate increase. The results came from multiple reactions, including the reaction of 4-Bromobenzonitrile(cas: 623-00-7Electric Literature of C7H4BrN)

4-Bromobenzonitrile(cas: 623-00-7) has been used in the synthesis of 4-iodobenzonitrile via photo-induced aromatic Finkelstein iodination reaction.Electric Literature of C7H4BrN 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