Month: October 2022

《Biaryl Cross-Coupling Enabled by Photo-Induced Electron Transfer》 was published in Advanced Synthesis & Catalysis in 2020. These research results belong to Hayashi, Hirohito; Wang, Bin; Wu, Xiangyang; Teo, Shi Jie; Kaga, Atsushi; Watanabe, Kohei; Takita, Ryo; Yeow, Edwin K. L.; Chiba, Shunsuke. Product Details of 105942-08-3 The article mentions the following:

A protocol for aryl cross-coupling of electron-deficient aryl halides ArX (Ar = 3-formylphenyl, 4-formylfuran-2-yl, 2-(methoxycarbonyl)pyrimidin-5-yl, etc.; X = Br, Cl) with electron-rich (hetero)arenes Ar1H (Ar1 = Ph, 1-methyl-1H-pyrrol-2-yl, pyrazin-2-yl, etc.) that is driven solely by violet light was reported. This process takes advantage of formation of photo-excited state of electron-deficient aryl halides, that are reduced by electron-rich (hetero)arenes to form a pair of aryl anion and cation radicals. The resulting aryl anion radicals of aryl halides undergo mesolysis of the carbon-halogen bond to generate aryl radicals, that are coupled most likely with aryl cation radicals to afford functionalized biaryls ArAr1. In addition to this study using 4-Bromo-2-fluorobenzonitrile, there are many other studies that have used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Product Details of 105942-08-3) was used in this study.

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a reagent in the synthesis of picolinamide derivatives as a novel class of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors.Product Details of 105942-08-3 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
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Li, Gang; Yang, Liu; Liu, Jian-Jun; Zhang, Wei; Cao, Rui; Wang, Chao; Zhang, Zunting; Xiao, Jianliang; Xue, Dong published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Light-Promoted C-N Coupling of Aryl Halides with Nitroarenes》.Safety of 2-(3-Bromophenyl)acetonitrile The article contains the following contents:

A photochem. C-N coupling of aryl halides with nitroarenes is demonstrated for the first time. Catalyzed by a NiII complex in the absence of any external photosensitizer, readily available nitroarenes undergo coupling with a variety of aryl halides, providing a step-economic extension to the widely used Buchwald-Hartwig C-N coupling reaction. The method tolerates coupling partners with steric-congestion and functional groups sensitive to bases and nucleophiles. Mechanistic studies suggest that the reaction proceeds via the addition of an aryl radical, generated from a NiI/NiIII cycle, to a nitrosoarene intermediate. In the experimental materials used by the author, we found 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Safety of 2-(3-Bromophenyl)acetonitrile)

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.Safety of 2-(3-Bromophenyl)acetonitrile

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Tang, Shi; Xu, Zhen-Hua; Liu, Ting; Wang, Shuo-Wen; Yu, Jian; Liu, Jian; Hong, Yu; Chen, Shi-Lu; He, Jin; Li, Jin-Heng published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Radical 1,4-Aryl Migration Enabled Remote Cross-Electrophile Coupling of α-Amino-β-Bromo Acid Esters with Aryl Bromides》.Recommanded Product: 2-Bromobenzonitrile The article contains the following contents:

Here an unprecedented, efficient nickel-catalyzed radical relay was reported for the remote cross-electrophile coupling of β-bromo-α-benzylamino acid esters with aryl bromides via 1,4-aryl migration/arylation cascades. β-Bromo-α-benzylamino acid esters were considered as unique mol. scaffolds allowing for aryl migration reactions, which were conceptually novel variants for the radical Truce-Smiles rearrangement. This reaction enabled the formation of two new C(sp3)-C(sp2) bonds using a bench-stable Ni/bipyridine/Zn system featuring a broad substrate scope and excellent diastereoselectivity, which provided an effective platform for the remote aryl group migration and arylation of amino acid esters via redox-neutral C(sp3)-C(sp2) bond cleavage. Mechanistically, this cascade reaction was accomplished by combining two powerful catalytic cycles consisting of a cross-electrophile coupling and radical 1,4-aryl migration through the generation of C(sp3)-centered radical intermediates from the homolysis of C(sp3)-Br bonds and the switching of the transient alkyl radical into a robust α-aminoalkyl radical. The experimental process involved the reaction of 2-Bromobenzonitrile(cas: 2042-37-7Recommanded Product: 2-Bromobenzonitrile)

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. This substrate molecule undergoes a palladium-catalyzed coupling reaction to form an aromatic ring. The light emission from this reaction can be seen in the reaction solution.Recommanded Product: 2-Bromobenzonitrile

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Hu, Rong; Tao, Yigao; Zhang, Xiaofeng; Su, Weiping published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《1,2-Aryl Migration Induced by Amide C-N Bond-Formation: Reaction of Alkyl Aryl Ketones with Primary Amines Towards α,α-Diaryl β,γ-Unsaturated γ-Lactams》.COA of Formula: C8H6BrN The article contains the following contents:

Rearrangement reactions incorporated into cascade reactions play an important role in rapidly increasing mol. complexity from readily available starting materials. Reported here is a Cu-catalyzed cascade reaction of α-(hetero)aryl-substituted alkyl (hetero)aryl ketones with primary amines that incorporates an unusual 1,2-aryl migration induced by amide C-N bond formation to produce a class of structurally novel α,α-diaryl β,γ-unsaturated γ-lactams in generally good-to-excellent yields. This cascade reaction has a broad substrate scope with respect to primary amines, allows a wide spectrum of (hetero)aryl groups to smoothly undergo 1,2-migration, and tolerates electronically diverse α-substituents on the (hetero)aryl ring of the ketones. Mechanistically, this 1,2-aryl migration may stem from the intramol. amide C-N bond formation which induces nucleophilic migration of the aryl group from the acyl carbon center to the electrophilic carbon center that is conjugated with the resulting iminium moiety. After reading the article, we found that the author used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5COA of Formula: C8H6BrN)

2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione or a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands.COA of Formula: C8H6BrN

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Nitrile – Wikipedia,
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Niknam, Esmaeil; Panahi, Farhad; Khalafi-Nezhad, Ali published an article in 2021. The article was titled 《Immobilized Pd on a NHC-functionalized metal-organic framework MIL-101(Cr): an efficient heterogeneous catalyst in the Heck and copper-free Sonogashira coupling reactions》, and you may find the article in Journal of Organometallic Chemistry.Safety of 4-Bromobenzonitrile The information in the text is summarized as follows:

A heterogeneous palladium catalyst system based on immobilization of palladium moieties on a N-heterocyclic carbene (NHC) modified metal organic framework (MOF) was developed for the Heck and copper-free Sonogashira coupling reactions. In order to prepare this catalyst system, first, MIL-101(Cr) was functionalized with NHC moieties through a post-synthetic modification (PSM) approach, and then Pd metal was stabilized on the prepared MIL-101(Cr)-NHC substrate. This material was characterized using various microscopic and spectroscopic techniques and then was used as an efficient heterogeneous Pd catalyst system in the Heck and copper-free Sonogashira reactions. Results of the heterogeneity tests showed that the Pd-NHC-MIL-101(Cr) catalyst can efficiently catalyzed these coupling reactions heterogeneously and no remarkable changes observed in the morphol. and structure of MIL-101(Cr) template during the reaction progress. Also, existence of palladium nanoparticles immobilized on the MOF structure affirmed by the TEM and XPS anal. confirmed the oxidation state of Pd. A variety of alkene and alkyne derivatives were synthesized in good to excellent yields using this heterogeneous Pd catalyst system under normal conditions. More importantly Pd-NHC-MIL-101(Cr) catalyst was simply recovered from the reaction medium without remarkable decreasing in its catalytic activities after five times of reusability. The ICP anal. showed the very low Pd and Cr metals leaching, representing high stability and applicability of this catalyst in Pd coupling reactions. The experimental part of the paper was very detailed, including the reaction process of 4-Bromobenzonitrile(cas: 623-00-7Safety 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.Safety 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,
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Kaloglu, Murat; Slimani, Ichraf; Ozdemir, Namik; Gurbuz, Nevin; Hamdi, Naceur; Ozdemir, Ismail published an article in 2021. The article was titled 《The direct C(sp2)-H functionalization and coupling of aromatic N-heterocycles with (hetero)aryl bromides by [PdX2(imidazolidin-2-ylidene)(Py)] catalysts》, and you may find the article in Journal of Organometallic Chemistry.Category: nitriles-buliding-blocks The information in the text is summarized as follows:

A series of air- and moisture-stable imidazolidin-2-ylidene-based new palladium complexes with the general formula [PdX2(NHC)(Py)] were synthesized (NHC = N-heterocyclic carbene, Py = pyridine, X = Cl or I). The structures of the palladium complexes were characterized by different techniques such as 1H NMR, 13C NMR, FT-IR spectroscopy and elemental anal. The more detailed structural characterization of one of the palladium complex was determined by single-crystal X-ray diffraction study. The catalytic activities of all palladium complexes were tested in the direct arylation of five-membered aromatic N-heterocycles such as 3,5-dimethylisoxazole and 1-methyl-1H-pyrrole-2-carboxaldehyde with (hetero)aryl bromides in presence of 1 mol% catalyst loading at 120°C. Desired products were obtained in moderate to good yields. In addition to this study using 2-Bromobenzonitrile, there are many other studies that have used 2-Bromobenzonitrile(cas: 2042-37-7Category: nitriles-buliding-blocks) was used in this study.

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.Category: nitriles-buliding-blocks

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Nitrile – Wikipedia,
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Zhu, Ruiheng; Reddy, Ramesh; Ding, Man; Xu, Ming; Deng, Chaoyi; Tadayon, Sam; Li, Hui; Depew, Kristopher; Lane, Benjamin published an article in 2021. The article was titled 《Development and Scale-Up of a Continuous Manufacturing Process for a Hydrazine Condensation Reaction》, and you may find the article in Organic Process Research & Development.COA of Formula: C9H7NO The information in the text is summarized as follows:

The development of a continuous manufacturing process for a hydrazine condensation reaction at high temperature was reported. This continuous process represented a safer approach to manufacture 3-phenyl-1H-pyrazol-5-amine at scale and exhibited better impurity control compared to a traditional batch process. A controlled crystallization allowed consistently low levels of residual hydrazine (<20 ppm) in isolated solids for further processing to final drug substance. The scalability and robustness of the continuous process was demonstrated at 3 kg scale with a throughput of 0.5 kg/h.3-Oxo-3-phenylpropanenitrile(cas: 614-16-4COA of Formula: C9H7NO) 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.COA of Formula: C9H7NO

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In 2022,Wang, Hui; Han, Wangyujing; Noble, Adam; Aggarwal, Varinder K. published an article in Angewandte Chemie, International Edition. The title of the article was 《Dual Nickel/Photoredox-Catalyzed Site-Selective Cross-Coupling of 1,2-Bis-Boronic Esters Enabled by 1,2-Boron Shifts》.Name: 2-Bromobenzonitrile The author mentioned the following in the article:

Site-selective transition-metal-catalyzed mono-deboronative cross-couplings of 1,2-bis-boronic esters are valuable methods for the synthesis of functionalized organoboron compounds However, such cross-couplings are limited to reaction of the sterically less hindered primary boronic ester. Herein, we report a nickel/photoredox-catalyzed mono-deboronative arylation of 1,2-bis-boronic esters that is selective for coupling of the more sterically hindered secondary/tertiary position. This is achieved by taking advantage of a 1,2-boron shift of primary β-boryl radicals to the thermodynamically favored secondary/tertiary radicals, which are subsequently intercepted by the nickel catalyst to enable arylation. The mild conditions are amenable to a broad range of aryl halides to give β-aryl boronic ester products in good yields and with high regioselectivity. This method also allows stereodivergent coupling of cyclic cis-1,2-bis-boronic esters to give trans-substituted products. The results came from multiple reactions, including the reaction of 2-Bromobenzonitrile(cas: 2042-37-7Name: 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.Name: 2-Bromobenzonitrile

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Nitrile – Wikipedia,
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HPLC of Formula: 31938-07-5In 2017 ,《Structural optimization elaborates novel potent Akt inhibitors with promising anticancer activity》 appeared in European Journal of Medicinal Chemistry. The author of the article were Liu, Yang; Yin, Yanzhen; Zhang, Zhen; Li, Carrie J.; Zhang, Hui; Zhang, Daoguang; Jiang, Changying; Nomie, Krystle; Zhang, Liang; Wang, Michael L.; Zhao, Guisen. The article conveys some information:

Targeting of Akt has been validated as a well rationalized approach to cancer treatment, and represents a promising therapeutic strategy for aggressive hematol. malignancies. We describe herein an exploration of novel Akt inhibitors for cancer therapy through structural optimization of previously described 4-(piperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine derivatives Our studies yielded a novel series of pyrrolopyrimidine based phenylpiperidine carboxamides capable of potent inhibition of Akt1. Notably, I exhibited robust antiproliferative effects in both mantle cell lymphoma cell lines and primary patient tumor cells. Low micromolar doses of 10h induced cell apoptosis and cell cycle arrest in G2/M phase, and significantly downregulated the phosphorylation of Akt downstream effectors GSK3β and S6 in Jeko-1 cells.2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5HPLC of Formula: 31938-07-5) was used in this study.

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

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Application In Synthesis of 4-Cyanobenzyl bromideIn 2020 ,《6-Nitro-1-benzylquinolones exhibiting specific antitubercular activity》 was published in Chemical Biology & Drug Design. The article was written by Beteck, Richard M.; Jordaan, Audrey; Swart, Tarryn; Van Der Kooy, Frank; Warner, Digby F.; Hoppe, Heinrich C.; Legoabe, Lesetja J.. The article contains the following contents:

In this study, we synthesized novel nitro quinolone-based compounds and tested them in vitro against a panel of Gram-pos. and Gram-neg. pathogens including Mycobacterium tuberculosis (MTB), Pseudomonas aeruginosa, Acinetobacter baumannii, Klebsiella pneumonia, Staphylococcus aureus, and Escherichia coli for antibacterial activities and also against HeLa cells for overt cytotoxicity. Compound I was identified as a non-toxic, potent hit with selective activity (MIC90 < 0.24μM) against MTB. I, however, showed no activity against DprE1 mutant, suggesting DprE1 as the likely target for this compound class. In the experiment, the researchers used 4-Cyanobenzyl bromide(cas: 17201-43-3Application In Synthesis of 4-Cyanobenzyl bromide)

4-Cyanobenzyl bromide(cas: 17201-43-3) can reacts with 2H-tetrazole in the presence of KOH to yield 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile. And it may be used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile.Application In Synthesis of 4-Cyanobenzyl bromide

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Nitrile – Wikipedia,
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