Month: October 2022

Kim, Young Ha; Lee, Hyuk; Kim, Yeong Joon; Kim, Bum Tae; Heo, Jung-Nyoung published an article on January 18 ,2008. The article was titled 《Direct One-Pot Synthesis of Phenanthrenes via Suzuki-Miyaura Coupling/Aldol Condensation Cascade Reaction》, and you may find the article in Journal of Organic Chemistry.Related Products of 325141-71-7 The information in the text is summarized as follows:

An efficient cascade reaction was developed where a Suzuki-Miyaura coupling is followed by an aldol condensation, for the construction of phenanthrene derivatives using microwave irradiation For example, the reaction of Me 2-bromophenylacetamide with 2-formylphenylboronic acid in the presence of a palladium catalyst and a base provided a biaryl intermediate, which underwent in situ cyclization to afford the corresponding phenanthrene I in high yield. This methodol. was used to synthesis a fluorescent phenanthrene excimer by bromination of 10-methylphenanthrene Et ester, a product from the previous cascade reaction, followed by lactamization with methylamine. The results came from multiple reactions, including the reaction of 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile(cas: 325141-71-7Related Products of 325141-71-7)

2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile(cas: 325141-71-7) 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.Related Products of 325141-71-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2003,Langer, Peter; Anders, Joachim T.; Weisz, Klaus; Jaehnchen, Judith published 《Efficient synthesis of 2-alkylidene-3-iminoindoles, indolo[1,2-b]isoquinolin-5-ones, δ-carbolines, and indirubines by domino and sequential reactions of functionalized nitriles》.Chemistry – A European Journal published the findings.Application of 31938-07-5 The information in the text is summarized as follows:

The sodium hydride mediated cyclization of arylacetonitriles with oxalic acid bis(imidoyl) dichlorides, aza-analogs of oxalyl chloride, afforded functionalized 2-alkylidene-3-iminoindoles with very good regio- and E/Z selectivity. Excellent chemoselectivities were observed for functionalized substrates. Based on these results a domino “”cyclization-lactamization”” reaction of bis(imidoyl) chlorides with Me 2-(cyanomethyl)benzoate was developed. This process allowed a convenient one-pot synthesis of indolo[1,2-b]isoquinolin-5-ones related to tryptanthrin. A new and convenient synthesis of δ-carbolines by intramol. electrocyclization-elimination reactions of 2-alkylidene-3-iminoindoles was developed. It was shown that δ-carbolines selectively bind to triplex or duplex DNA (intercalation). Indirubine analogs were prepared by deprotection and lactonization of functionalized 2-alkylidene-3-iminoindoles. In the experiment, the researchers used many compounds, for example, 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Application of 31938-07-5)

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.Application of 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2013,Wu, Hai-Qiu; Yan, Zi-Hong; Chen, Wen-Xue; He, Qiu-Qin; Chen, Fen-Er; De Clercq, Erik; Balzarini, Jan; Daelemans, Dirk; Pannecouque, Christophe published 《Towards new C6-rigid S-DABO HIV-1 reverse transcriptase inhibitors: Synthesis, biological investigation and molecular modeling studies》.Bioorganic & Medicinal Chemistry published the findings.SDS of cas: 31938-07-5 The information in the text is summarized as follows:

A series of C6-rigid S-DABO analogs characterized by a substituted benzoyl group at C6 position of the pyrimidine ring has been synthesized and biol. evaluation as NNRTIs against wild-type HIV-1 strain IIIB, double RT mutant (K103N + Y181C) strain RES056 as well as HIV-2 strain ROD in MT-4 cell cultures. Most of the compounds exhibited moderate antiviral activities. Among them, compound 7q displayed the highest anti-HIV-1 activity with an EC50 value of 0.26 μM and a selectivity index (SI) of 541. The preliminary structure-activity relationship (SAR) of these new S-DABOs was investigated, the target RT was confirmed and docking study was performed. After reading the article, we found that the author used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5SDS of cas: 31938-07-5)

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.SDS of cas: 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Cellulose (Dordrecht, Netherlands) included an article by Dong, Yahao; Bi, Jiajun; Zhu, Dajian; Meng, Di; Ming, Shujun; Guo, Wen; Chen, Zhen; Liu, Qian; Guo, Lei; Li, Tao. Recommanded Product: 623-00-7. The article was titled 《Functionalized cellulose with multiple binding sites for a palladium complex catalyst: synthesis and catalyst evaluation in Suzuki-Miyaura reactions》. The information in the text is summarized as follows:

Due to their eco-friendly nature, polysaccharides are desirable supporting materials in organic transformations. Nevertheless, as is the case for other supports, polysaccharides have to face the issue of seeking more binding sites via multifunctional structures to capture metal species in the catalyst, which enhance stability and promote catalytic performance in aforementioned process. In this paper, an environmentally-friendly and multifunctional cellulose supported Pd(II)-Schiff base complex is fabricated and applied in the formation of different biaryls under mild ambient conditions. The results of thermal anal. reveal that the composite has high thermal stability. The as-prepared catalyst demonstrates to be a robust and efficient catalyst with more than 90% yields in H2O: EtOH (1:1) at 70° by using 0.30 mol% of catalyst under air towards the coupling of various substituted aryl halides and phenylboronic acids. Moreover, identified by ICP-OES anal., the green Pd(II) catalyst displays higher metal content (1.93%) in comparison with the direct deposition of Pd particles on cellulose (0.93%), and prevents the metal leaching (< 1%) via the coordination interaction of multiple capturing sites (-OH, Schiff base and pyridyl moieties) with palladium. The resultant catalyst is characterized by FT-IR, TGA, XRD, SEM, TEM, XPS, CP/MAS 13C-NMR, and ICP-OES examination Also, this green catalyst is able to be retrieved in five cycles with simple centrifugation. Notably, the authors propose a plausible multifunctional catalyst complex. The present study offers a novel and effective supported catalyst, which broadens the contributions of polysaccharides in green catalysis. The experimental process involved the reaction of 4-Bromobenzonitrile(cas: 623-00-7Recommanded Product: 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,Recommanded Product: 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

The author of 《Pyrrolopyrimidine vs. Imidazole-Phenyl-Thiazole Scaffolds in Nonpeptidic Dimerization Inhibitors of Leishmania infantum Trypanothione Reductase》 were Revuelto, Alejandro; Ruiz-Santaquiteria, Marta; de Lucio, Hector; Gamo, Ana; Carriles, Alejandra A.; Gutierrez, Kilian Jesus; Sanchez-Murcia, Pedro A.; Hermoso, Juan A.; Gago, Federico; Camarasa, Maria-Jose; Jimenez-Ruiz, Antonio; Velazquez, Sonsoles. And the article was published in ACS Infectious Diseases in 2019. Application In Synthesis of 4-Bromo-2-fluorobenzonitrile The author mentioned the following in the article:

Disruption of protein-protein interactions of essential oligomeric enzymes by small mols. represents a significant challenge. We recently reported some linear and cyclic peptides derived from an α-helical region present in the homodimeric interface of Leishmania infantum trypanothione reductase (Li-TryR) that showed potent effects on both dimerization and redox activity of this essential enzyme. Here, we describe our first steps toward the design of nonpeptidic small-mol. Li-TryR dimerization disruptors using a proteomimetic approach. The pyrrolopyrimidine and the 5-6-5 imidazole-phenyl-thiazole α-helix-mimetic scaffolds were suitably decorated with substituents that could mimic three key residues (K, Q, and I) of the linear peptide prototype (PKIIQSVGIS-Nle-K-Nle). Extensive optimization of previously described synthetic methodologies was required. A library of 15 compounds bearing different hydrophobic alkyl and aromatic substituents was synthesized. The imidazole-phenyl-thiazole-based analogs outperformed the pyrrolopyrimidine-based derivatives in both inhibiting the enzyme and killing extracellular and intracellular parasites in cell culture. The most active imidazole-phenyl-thiazole compounds 3e and 3f inhibit Li-TryR and prevent growth of the parasites at low micromolar concentrations similar to those required by the peptide prototype. The intrinsic fluorescence of these compounds inside the parasites visually demonstrates their good permeability in comparison with previous peptide-based Li-TryR dimerization disruptors. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Application In Synthesis of 4-Bromo-2-fluorobenzonitrile)

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Nickel-Catalyzed Tandem Reaction of Functionalized Arylacetonitriles with Arylboronic Acids in 2-MeTHF: Eco-Friendly Synthesis of Aminoisoquinolines and Isoquinolones》 was published in Chemistry – An Asian Journal in 2020. These research results belong to Zhen, Qianqian; Chen, Lepeng; Qi, Linjun; Hu, Kun; Shao, Yinlin; Li, Renhao; Chen, Jiuxi. Reference of 4-Bromo-2-fluorobenzonitrile The article mentions the following:

The first example of the nickel-catalyzed tandem addition/cyclization of 2-(cyanomethyl)benzonitriles R1-2-(NCCH(R2))C6H3CN (R1 = H, 4-Me, 6-Ph, 5-Br, etc.; R2 = H, Ph, thiophen-3-yl, i-Pr, etc.) with arylboronic acids ArB(OH)2 (Ar = Ph, thiophen-3-yl, benzo[d][1,3]dioxol-5-yl, etc.) in 2-MeTHF has been developed, which provides the facile synthesis of aminoisoquinolines I (R1 = H, 6-Me, 8-Ph, 7-Br, etc.) with good functional group tolerance under mild conditions. This chem. has also been successfully applied to the synthesis of isoquinolones II by the tandem reaction of Me 2-(cyanomethyl)benzoates with arylboronic acids. The use of the bio-based and green solvent 2-MeTHF as the reaction medium makes the synthesis process environmentally benign. The synthetic utility of this chem. is also indicated by the synthesis of biol. active mols. The experimental process involved the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Reference of 4-Bromo-2-fluorobenzonitrile)

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Synthesis and Characterization of Ultrapure HKUST-1 MOFs as Reusable Heterogeneous Catalysts for the Green Synthesis of Tetrazole Derivatives》 was published in ChemistrySelect in 2020. These research results belong to Kal-Koshvandi, Afsaneh Taheri; Maleki, Ali; Tarlani, Aliakbar; Soroush, Maral Rahim. Recommanded Product: 4-Fluorobenzonitrile The article mentions the following:

An ultrapure HKUST-1 MOFs synthesized through a precised methodol. as a heterogeneous catalyst for a green approach to the synthesis of tetrazole derivatives via two-, three-, and four-component reactions in milder reaction conditions was presented. Various preparation methods to produce HKUST-1 such as microwave irradiation, reflux, hydrothermal technique, and ultrasonication was precisely compared and it was proved that the best result was obtained during the hydrothermal technique. This was the first design, preparation, characterization and application in the present of HKUST-1 MOFs to the synthesis of the biol. and pharmaceutically important tetrazole compounds in green conditions. Moreover, plausible mechanisms of reactions was suggested for the catalytic activity of the presented catalyst. The catalyst was characterized by various techniques such as FT-IR, SEM, EDX, and XRD. Addnl., HKUST-1 was recoverable as well as reusable without any significant loss of its activity, which strongly supports the heterogeneous nature of the catalyyst. This novel catalysis protocol offered several advantages such as eco-friendly conditions, lower reaction time, milder reaction conditions, excellent catalytic activity and an easy separation of the catalyst make it a good heterogeneous system. The experimental process involved the reaction of 4-Fluorobenzonitrile(cas: 1194-02-1Recommanded Product: 4-Fluorobenzonitrile)

4-Fluorobenzonitrile(cas: 1194-02-1) is used as chemical intermediate, solvent for perfumes and pharmaceuticals, stabilizer for chlorinated solvents, HPLC analysis, catalyst and component of transition-metal complex catalysts.Recommanded Product: 4-Fluorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Photoactive Metal-Organic Framework for the Reduction of Aryl Halides by the Synergistic Effect of Consecutive Photoinduced Electron-Transfer and Hydrogen-Atom-Transfer Processes》 was written by He, Jiachen; Li, Jie; Han, Qiuxia; Si, Chen; Niu, Guiqin; Li, Mingxue; Wang, Jingping; Niu, Jingyang. Application of 623-00-7 And the article was included in ACS Applied Materials & Interfaces in 2020. The article conveys some information:

Consecutive photoinduced electron transfer (ConPET) has advantages on overcoming the current energetic limitation of visible-light photoredox catalysis for utilizing the energies of two photons in one catalytic cycle. A heterogeneous approach for radical chain reduction of various aryl bromides and chlorides without adding any cocatalyst is introduced by incorporating polyoxometalates (POMs) and amine catalysts into a naphthalenediimide (NDI)-based polymer. CoW-DPNDI-PYI exhibits high activity in the photocatalytic reduction of aryl halides by the synergistic effects of ConPET and hydrogen-atom transfer (HAT) processes and an enzyme-mimicking CO2 cycloaddition reaction. The ConPET process with N,N′-bis(4-pyridylmethyl)naphthalenediimide (DPNDI) facilitates effective solar energy conversion. POMs and amine catalysts, as efficient HAT catalysts and electron donors, improve the generation of ConPET process. The success of this work demonstrates the great application of the synergistic effects of ConPET and HAT processes in heterogeneous photocatalysis C-H arylation. In the experiment, the researchers used many compounds, for example, 4-Bromobenzonitrile(cas: 623-00-7Application of 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.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

De Jesus Silva, Jordan; Bartalucci, Niccolo; Jelier, Benson; Grosslight, Samantha; Gensch, Tobias; Schuenemann, Claas; Mueller, Bernd; Kamer, Paul C. J.; Coperet, Christophe; Sigman, Matthew S.; Togni, Antonio published their research in Helvetica Chimica Acta in 2021. The article was titled 《Development and Molecular Understanding of a Pd-Catalyzed Cyanation of Aryl Boronic Acids Enabled by High-Throughput Experimentation and Data Analysis》.SDS of cas: 1194-02-1 The article contains the following contents:

A synthetic method for the palladium-catalyzed cyanation of aryl boronic acids RB(OH)2 (R = 4-fluorophenyl, naphthalen-2-yl, thiophen-3-yl, etc.) using bench stable and non-toxic N-cyanosuccinimide has been developed. High-throughput experimentation facilitated the screen of 90 different ligands and the resultant statistical data anal. identified that ligand σ-donation, π-acidity and sterics are key drivers that govern yield. Categorization into three ligand groups – monophosphines, bisphosphines and miscellaneous – was performed before the anal. For the monophosphines, the yield of the reaction increases for strong σ-donating, weak π-accepting ligands, with flexible pendant substituents. For the bisphosphines, the yield predominantly correlates with ligand lability. The applicability of the designed reaction to a wider substrate scope was investigated, showing good functional group tolerance in particular with boronic acids bearing electron-withdrawing substituents. This work outlines the development of a novel reaction, coupled with a fast and efficient workflow to gain understanding of the optimal ligand properties for the design of improved palladium cross-coupling catalysts. The experimental process involved the reaction of 4-Fluorobenzonitrile(cas: 1194-02-1SDS of cas: 1194-02-1)

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Rzhevskiy, Sergey A.; Topchiy, Maxim A.; Bogachev, Vasilii N.; Minaeva, Lidiya I.; Cherkashchenko, Ilia R.; Lavrov, Konstantin V.; Sterligov, Grigorii K.; Nechaev, Mikhail S.; Asachenko, Andrey F. published their research in Mendeleev Communications in 2021. The article was titled 《Solvent-free palladium-catalyzed C-O cross-coupling of aryl bromides with phenols》.Product Details of 2042-37-7 The article contains the following contents:

A new solvent-free procedure for C-O cross-coupling between phenols ArOH (Ar = Ph, 4-chlorophenyl, 2-isopropylphenyl, etc.) and aryl bromides Ar1Br (Ar1 = 4-methylphenyl, 2-cyanophenyl, 3,5-bis(trifluoromethyl)phenyl, etc.) comprising of Pd2(dba)3/ButBrettPhos catalytic system is efficient for substrates bearing donor or acceptor, as well as bulky substituents.2-Bromobenzonitrile(cas: 2042-37-7Product Details of 2042-37-7) was used in this study.

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.Product Details of 2042-37-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts