Month: October 2022

In 2017,Schischko, Alexandra; Ren, Hongjun; Kaplaneris, Nikolaos; Ackermann, Lutz published 《Bioorthogonal Diversification of Peptides through Selective Ruthenium(II)-Catalyzed C-H Activation》.Angewandte Chemie, International Edition published the findings.Synthetic Route of C8H6BrN The information in the text is summarized as follows:

Methods for the chemoselective modification of amino acids and peptides are powerful techniques in biomol. chem. Among other applications, they enable the total synthesis of artificial peptides. In recent years, significant momentum has been gained by exploiting palladium-catalyzed cross-coupling for peptide modification. Despite major advances, the prefunctionalization elements on the coupling partners translate into undesired byproduct formation and lengthy synthetic operations. In sharp contrast, we herein illustrate the unprecedented use of versatile ruthenium(II)carboxylate catalysis for the step-economical late-stage diversification of α- and β-amino acids, as well as peptides, through chemo-selective C-H arylation under racemization-free reaction conditions. The ligand-accelerated C-H activation strategy proved water-tolerant and set the stage for direct fluorescence labeling as well as various modes of peptide ligation with excellent levels of positional selectivity in a bioorthogonal fashion. The synthetic utility of our approach is further demonstrated by twofold C-H arylations for the complexity-increasing assembly of artificial peptides within a multicatalytic C-H activation manifold. The experimental process involved the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Synthetic Route of C8H6BrN)

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.Synthetic Route of C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Molecular hybridization approach for phenothiazine incorporated 1,2,3-triazole hybrids as promising antimicrobial agents: Design, synthesis, molecular docking and in silico ADME studies》 were Reddyrajula, Rajkumar; Dalimba, Udayakumar; Madan Kumar, S.. And the article was published in European Journal of Medicinal Chemistry in 2019. Reference of 4-Cyanobenzyl bromide The author mentioned the following in the article:

The synthesis a library consisting of four sets of phenothiazine incorporated 1,2,3-triazole compounds using mol. hybridization approach. The new hybrid mols. were synthesized and screened for in-vitro growth inhibition activity against Mycobacterium tuberculosis H37Rv strain (ATCC-27294). Among the tested compounds, nineteen compounds exhibited significant activity with MIC value 1.6 μg/mL, which was two fold higher than the MIC value of standard first-line TB drug Pyrazinamide. In addition, all these compounds were proved to be non-toxic (with selective index > 40) against VERO cell lines. However, these compounds did not inhibit significantly the growth of Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa strains: the activity profile was similar to that observed for standard anti-TB drugs (isoniazid and pyrazinamide), indicating the specificity of these compounds towards the Mycobacterium tuberculosis strain. The mol. docking studies against two target enzymes (Inh A and CYP121) to further validate the antitubercular potency of these mols. was reported. Furthermore, prediction of in silico-ADME and pharmacokinetic parameters indicated that these compounds were good oral bioavailability. The results suggested that these phenothiazine incorporated 1,2,3-triazole compounds were a promising class of mol. entities for the development of new antitubercular leads.4-Cyanobenzyl bromide(cas: 17201-43-3Reference of 4-Cyanobenzyl bromide) was used in this study.

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.Reference of 4-Cyanobenzyl bromide

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Protective effects of piper betel phenol, hydroxychavicol and its derivatives against rotenone induced neurotoxicity: synthesis, in vitro and in vivo efficacy studies》 were Ghanta, Venkata Rao; Pasula, Aparna; Pindiprolu, Sai Kiran S. S.; Krishnamurthy, Praveen T.; Ravi, Chandran J. K.; Raman, Balamurali. And the article was published in World Journal of Pharmaceutical Research in 2019. Quality Control of 4-Bromo-2-fluorobenzonitrile The author mentioned the following in the article:

Hydroxychavicol or 4-Allylpyrocatechol (4-APC) is a Piper betel phenol, reported to modulate vital pathways involved in inflammation and oxidative stress. However, the potential neuro protective benefits of 4APC against neurodegeneration, where similar pathways are involved was not reported and hence 4APC and its derivatives (3a – 3j) were evaluated for their possible neuroprotective activity against rotenone induced neurotoxicity. In the present study 4-allyl pyrocatechol (APC) and its derivatives (3a – 3j) were synthesized via heck coupling with aryl bromides and evaluated for their possible in vitro and in vivo neuroprotective activity against rotenone induced neurotoxicity in SH-SY5Y cell lines and in Swiss albino mice, resp. In the in vitro studies, among the tested compounds, the 4APC and its derivative, 3c, have shown significant protection against rotenone induced cytotoxicity. In mice, these 2 mols. significantly prevent the rotenone (3 mg/kg, s.c.) induced changes in grip strength, locomotor activity and oxidative & inflammatory stress markers at a tested oral dose of 20/mg/kg. The results came from multiple reactions, including the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Quality Control of 4-Bromo-2-fluorobenzonitrile)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.Quality Control of 4-Bromo-2-fluorobenzonitrile It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Green synthesis of a palladium nanocatalyst anchored on magnetic lignin-chitosan beads for synthesis of biaryls and aryl halide cyanation》 was published in International Journal of Biological Macromolecules in 2020. These research results belong to Baran, Talat; Sargin, Idris. COA of Formula: C7H4BrN The article mentions the following:

Aryl nitriles, Ar-C=N, and biaryls are important precursors of many compounds commonly used in the industry. Production of aryl nitriles and biaryls through a facile method is therefore of significance. In the study the synthesis of aryl nitriles and biaryls with various substituted groups was successfully achieved using a simple but efficient palladium nanocatalyst system. The nano-catalyst system, (Pd NPs@Fe3O4/lignin/chitosan), was easily prepared by decorating palladium nanoparticles on the magnetic lignin/chitosan microbeads without using any toxic reducing agents. Characterization of the catalyst revealed that the size of palladium nanoparticles was lower than 20 nm and the palladium nanoparticles were homogeneously dispersed on the catalyst support; Fe3O4/lignin/chitosan. The catalytic activity of Pd NPs@Fe3O4/lignin/chitosan was tested in the synthesis of a number of various aryl nitriles and biaryls. Pd NPs@Fe3O4/lignin/chitosan catalyzed the conversion of different aryl halides into aryl nitriles in the presence of K4[Fe(CN)6] by producing conversion yields as high as 97%. The system also exhibited good reactions yields up to 98% for synthesis of biaryls. More importantly, due to its magnetic nature, the used catalyst was easily recovered from the reaction media with a magnet, and regenerated and reused for seven runs. The experimental process involved the reaction of 4-Bromobenzonitrile(cas: 623-00-7COA of Formula: C7H4BrN)

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,COA of Formula: 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

《Cyanation of aryl halides and Suzuki-Miyaura coupling reaction using palladium nanoparticles anchored on developed biodegradable microbeads》 was written by Baran, Talat; Nasrollahzadeh, Mahmoud. SDS of cas: 623-00-7 And the article was included in International Journal of Biological Macromolecules in 2020. The article conveys some information:

This work reported, green synthesis of palladium nanoparticles (Pd NPs) on the developed biodegradable microbeads as stabilizers, featuring chitosan, agarose and beta-cyclodextrin, investigation of the catalytic role of the Pd NPs prepared in the Suzuki-Miyaura and cyanation reactions. Pd NPs@microcapsules (CAP) converted a series of aryl halides to biphenyl compounds with yields ranging from 79 to 98%. Pd NPs@CAP was highly active in the cyanation of different aryl bromides and iodides using K4[Fe(CN)6] and was used to prepare benzonitriles with a yield of up to 97%. More importantly, Pd NPs@CAP was easily recovered from the reaction mixture and successfully reused seven consecutive times in the Suzuki-Miyaura and cyanation reactions. This significant features of Pd NPs@CAP were ease of purification of desired biaryls and benzonitriles and production of no byproducts in both catalytic reactions. In the experimental materials used by the author, we found 4-Bromobenzonitrile(cas: 623-00-7SDS of cas: 623-00-7)

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

Recommanded Product: 2-BromobenzonitrileIn 2022 ,《Scalable, Chemoselective Nickel Electrocatalytic Sulfinylation of Aryl Halides with SO2》 was published in Angewandte Chemie, International Edition. The article was written by Lou, Terry Shing-Bong; Kawamata, Yu; Ewing, Tamara; Correa-Otero, Guillermo A.; Collins, Michael R.; Baran, Phil S.. The article contains the following contents:

The sulfonyl fluorides ArSO2F [Ar = 2-MeOC6H4, 4-FC6H4, 3,5-di-MeC6H3, etc.] were synthesized via electrochem. sulfinylation and fluorination of aryl iodides and bromides through aryl sulfinate intermediate using an inexpensive Ni-electrocatalytic protocol. The reaction exhibited a broad scope, used stock solution of simple SO2 as sulfur source, and could be scaled up in batch and recycle flow settings. The limitations of this reaction were clearly shown and put into context by benchmarking with state-of-the-art Pd-based methods. The experimental process involved the reaction of 2-Bromobenzonitrile(cas: 2042-37-7Recommanded Product: 2-Bromobenzonitrile)

2-Bromobenzonitrile(cas: 2042-37-7) belongs to a group of ortho-substituted bromobenzenes that have varying hepatotoxicity effects in the presence of rat liver microsomes in vitro. 2-Bromobenzonitrile is also used as a starting material to synthesize novel benzothiophene derivatives that were found to exhibit antibacterial and antifungal activity.Recommanded Product: 2-Bromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2017,Hendrick, Charles E.; Bitting, Katie J.; Cho, Seoyoung; Wang, Qiu published 《Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation》.Journal of the American Chemical Society published the findings.Product Details of 105942-08-3 The information in the text is summarized as follows:

Arene amination is achieved by site-selective C-H zincation followed by copper-catalyzed coupling with O-benzoylhydroxylamines under mild conditions. Key to this success is ortho-zincation mediated by lithium amidodiethylzincate base that is effective for a wide range of arenes, including nonactivated arenes bearing simple functionalities such as fluoride, chloride, ester, amide, ether, nitrile, and trifluoromethyl groups as well as heteroarenes including indole, thiophene, pyridine, and isoquinoline. An analogous C-H azidation is also accomplished using azidoiodinane for direct introduction of a useful azide group onto a broad scope of arenes and heteroarenes. These new transformations offer rapid access to valuable and diverse chem. space of aminoarenes. Their broad applications in organic synthesis and drug discovery are demonstrated in the synthesis of novel analogs of natural product (-)-nicotine and antidepressant sertraline by late-stage amination and azidation reactions. After reading the article, we found that the author used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Product Details of 105942-08-3)

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,
Nitriles – Chemistry LibreTexts

《Cobalt-Catalyzed Cross-Coupling of Functionalized Alkylzinc Reagents with (Hetero)Aryl Halides》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Lutter, Ferdinand H.; Grokenberger, Lucie; Spiess, Philipp; Hammann, Jeffrey M.; Karaghiosoff, Konstantin; Knochel, Paul. HPLC of Formula: 105942-08-3 The article mentions the following:

A combination of 10% CoCl2 and 20% 2,2′-bipyridine ligands enables cross-coupling of functionalized primary and secondary alkylzinc reagents RZnY (R = 3-phenylpropyl, 3-(2,5-dimethyl-1H-pyrrol-1-yl)propyl, cyclopropyl, etc.; Y = Cl, Br) with various (hetero)aryl halides R1X (R1 = 5-cyanopyridin-2-yl, quinolin-2-yl, pyrimidin-2-yl, etc.; X = Cl, Br). Couplings with 1,3- and 1,4-substituted cycloalkylzinc reagents R2ZnI (R2 = 3-methylcyclohexyl, 4-(1H-pyrrol-1-yl)cyclohexyl, (4R,4aS,6R,8aR)-4,4a-dimethyl-6-(propan-2-yl)-decahydronaphthalen-2-yl, etc.) proceeded diastereoselectively leading to functionalized heterocycles R1R2 with high diastereoselectivities of up to 98:2. Furthermore, alkynyl bromides R3CCBr (R3 = Ph, tris(propan-2-yl)silyl) react with primary and secondary alkylzinc reagents RZnY (R = 2-(1,3-dioxan-2-yl)ethyl, 4-phenylcyclohexyl; Y = Cl, I) providing the alkylated alkynes RCCR3. In addition to this study using 4-Bromo-2-fluorobenzonitrile, there are many other studies that have used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3HPLC of Formula: 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.HPLC of Formula: 105942-08-3 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Li, Haoyu; Liu, Yuliang; Chiba, Shunsuke published their research in Chemical Communications (Cambridge, United Kingdom) in 2021. The article was titled 《Anti-Markovnikov hydroarylation of alkenes via polysulfide anion photocatalysis》.Formula: C7H3BrFN The article contains the following contents:

A protocol for anti-Markovnikov hydroarylation of alkenes, e.g., 2,3-dihydrofuran with aryl halides ArX (Ar = (4-CO2CH3)C6H4, 2-naphthyl, 5-cyanothiophen-2-yl, etc.; X = Br, Cl) has been developed using polysulfide anions as photocatalysts in the presence of the Hantzsch ester and water under irradiation with visible light. The results came from multiple reactions, including the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Formula: C7H3BrFN)

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.Formula: C7H3BrFN 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2017,Mi, Rui-Jie; Sun, Jing; Kuhn, Fritz E.; Zhou, Ming-Dong; Xu, Zhaoqing published 《A meta-selective-C-H alkenylation of phenol-derivatives employing a traceless organosilicon template》.Chemical Communications (Cambridge, United Kingdom) published the findings.Electric Literature of C8H6BrN The information in the text is summarized as follows:

A traceless O-benzeneacetonitrile silyl template-directed meta-selective-C-H Heck alkenylation of phenols was realized with good yields and high selectivities. Etherification of phenol with 3-cyanomethylphenylsilyl substituents gives the directing template, 3-R2C(CN)C6H4SiiPr2OC6H4R1 (R1 = Me, MeO, halo, CF3, MeO2C), which undergoes meta-regioselective palladium-catalyzed Heck alkenylation with Et acrylate, giving cinnamates 3-R2C(CN)C6H4SiiPr2OC6H3R1-3-CH:CHCO2Et; the latter can be easily deprotected, leaving hydroxycinnamates 3-HOC6H3R1CH:CHCO2Et. The template was readily removable through F–promoted O-Si cleavage under extremely mild conditions or recyclable through a p-TSA catalyzed process. The product was successfully applied in the preparation of a series of meta-alkenylated aromatic compounds In the experiment, the researchers used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Electric Literature of C8H6BrN)

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.Electric Literature of C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts