Tag: 100-200

The author of 《Supported organometallic palladium catalyst into mesoporous channels of magnetic MCM-41 nanoparticles for phosphine-free C-C coupling reactions》 were Ghorbani-Choghamarani, Arash; Tahmasbi, Bahman; Hudson, Robert H. E.; Heidari, Ali. And the article was published in Microporous and Mesoporous Materials in 2019. Formula: C7H4BrN The author mentioned the following in the article:

Magnetic MCM-41 nanoparticles were synthesized via Fe3O4-doped into mesoporous channels of MCM-41 nanoparticles and further, a new organometallic complex of palladium was supported on its inner surface (Pd-imi@MCM-41/Fe3O4). This immobilized catalyst was applied as highly efficient, heterogeneous and magnetically recoverable nanocatalyst in the various C-C coupling reactions such as Suzuki-Miyaura and Mizoroki-Heck reactions under phosphine-free conditions at atm. pressure. This catalyst has advantages of both magnetic nanoparticles and mesoporous materials. The structure of prepared nanomaterial has been characterized by various techniques such as N2 adsorption-desorption isotherms, TEM, SEM, EDS, WDX, FT-IR, XRD, TGA, ICP, AAS, and VSM. SEM images of this catalyst demonstrate that the particles size are less than 100 nm in diameter VSM curve of the catalyst shows that this catalyst can be recovered using an external magnet; therefore, this catalyst can be reused for several times without significant loss of its catalytic efficiency or palladium leaching. Also, all products were obtained in high TON and TOF numbers, which reveals this catalyst has high activity and selectivity in described coupling reactions. Heterogeneity and stability of this nanocatalyst were confirmed by hot filtration test and AAS technique.4-Bromobenzonitrile(cas: 623-00-7Formula: C7H4BrN) 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.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

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

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

《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

《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

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

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

In 2014,Mahtab, Reena; Srivastava, Ashish; Gupta, Nishi; Kushwaha, Sandeep Kumar; Tripathi, Aradhna published 《Synthesis of novel 2-benzylbenzo[d] thiazole-6-sulfonamide derivatives as potential anti inflammatory agent》.Journal of Chemical and Pharmaceutical Sciences published the findings.Formula: C8H6BrN The information in the text is summarized as follows:

The benzothiazole derivatives such as substituted 2-benzylbenzo[d]thiazole-6-sulfonamides I [R = H, 2-HO, 2-MeO, 3-Br] were synthesized by using sulfa drugs from substituted benzyl bromides. All the newly synthesized benzothiazole derivatives showed considerable anti-inflammatory activity. The chem. structures of the synthesized compounds were confirmed by means of IR, 1H-NMR, mass spectral and elemental anal. These compounds were screened for anti-inflammatory activity by carrageenan induced paw edema method in rats at a dose of 100 mg/kg body weight Among the tested compounds of benzothiazole derivatives, compounds I [R = 2-OH, 2-OMe, 2,5-(F)2, 4-Br] exhibited some anti-inflammatory activity but compounds I [R = H, 2-F, 4-F, 4-Cl, 3-Br] were more potent when compared to standard drug celecoxib. The experimental part of the paper was very detailed, including the reaction process of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Formula: 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.Formula: C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Marcin, Lawrence R.; Higgins, Mendi A.; Zusi, F. Christopher; Zhang, Yunhui; Dee, Michael F.; Parker, Michael F.; Muckelbauer, Jodi K.; Camac, Daniel M.; Morin, Paul E.; Ramamurthy, Vidhyashankar; Tebben, Andrew J.; Lentz, Kimberley A.; Grace, James E.; Marcinkeviciene, Jovita A.; Kopcho, Lisa M.; Burton, Catherine R.; Barten, Donna M.; Toyn, Jeremy H.; Meredith, Jere E.; Albright, Charles F.; Bronson, Joanne J.; Macor, John E.; Thompson, Lorin A. published an article in Bioorganic & Medicinal Chemistry Letters. The title of the article was 《Synthesis and SAR of indole- and 7-azaindole-1,3-dicarboxamide hydroxyethylamine inhibitors of BACE-1》.Recommanded Product: 3-Formyl-1H-indole-6-carbonitrile The author mentioned the following in the article:

Heterocyclic replacement of the isophthalamide Ph ring in hydroxyethylamine (HEA) BACE-1 inhibitors was explored. A variety of indole-1,3-dicarboxamide HEAs I (X = CH; R1 = R2 = Et, n-Pr, n-Bu; R1 = n-Bu, R2 = H, Me; R3 = H, F, CN; R4 = H, F, Cl, CF3, CO2H, etc.; R5 = 3-MeOC6H4CH2; R6 = H, F) exhibited potent BACE-1 enzyme inhibition, but displayed poor cellular activity. Improvements in cellular activity and aspartic protease selectivity were observed for 7-azaindole-1,3-dicarboxamide HEAs I (X = N; R1 = Bu, n-pentyl, isopentyl, MeOCH2CH2, R2 = Me; R1 = cyclopropylmethyl, R2 = n-Pr; R1R2N = 2-ethoxymethyl-1-piperidinyl, etc.; R3 = R4 = H; R5 = 3-MeOC6H4CH2, 3-MeOC6H4CO, cyclopropyl, etc.; R6 = H, F). A methylprolinol-bearing azaindole I [X = N; R1R2N = (R)-2-methoxymethyl-1-pyrrolidinyl; R3 = R4 = H; R5 = 3-MeOC6H4CH2; R6 = F] demonstrated robust reductions in rat plasma Aβ levels, but did not lower rat brain Aβ due to poor central exposure. The same compound exhibited a high efflux ratio in a bidirectional Caco-2 assay and was likely a substrate of the efflux transporter P-glycoprotein. X-ray crystal structures are reported for two indole HEAs in complex with BACE-1. In the experiment, the researchers used many compounds, for example, 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Recommanded Product: 3-Formyl-1H-indole-6-carbonitrile)

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.Recommanded Product: 3-Formyl-1H-indole-6-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Murugesan, Kathiravan; Donabauer, Karsten; Koenig, Burkhard published an article in 2021. The article was titled 《Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(sp3)-H Bonds》, and you may find the article in Angewandte Chemie, International Edition.Quality Control of 4-Bromobenzonitrile The information in the text is summarized as follows:

The metal-free activation of C(sp3)-H bonds to value-added products is of paramount importance in organic synthesis. We report the use of the com. available organic dye 2,4,6-triphenylpyrylium tetrafluoroborate (TPP) for the conversion of methylarenes to the corresponding aryl nitriles via a photocatalytic process. Applying this methodol., a variety of cyanobenzenes have been synthesized in good to excellent yield under metal- and cyanide-free conditions. We demonstrate the scope of the method with over 50 examples including late-stage functionalization of drug mols. (celecoxib) and complex structures such as L-menthol, amino acids, and cholesterol derivatives Furthermore, the presented synthetic protocol is applicable for gram-scale reactions. In addition to methylarenes, selected examples for the cyanation of aldehydes, alcs. and oximes are demonstrated as well. Detailed mechanistic investigations have been carried out using time-resolved luminescence quenching studies, control experiments, and NMR spectroscopy as well as kinetic studies, all supporting the proposed catalytic cycle.4-Bromobenzonitrile(cas: 623-00-7Quality Control of 4-Bromobenzonitrile) 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.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