Tag: 100-200

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

《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

《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

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

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 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 1954,Journal of the Chemical Society included an article by Gray, G. W.; Jones, Brynmor. Safety of 5-Amino-1-naphthonitrile. The article was titled 《The preparation of 4- and 5-n-alkoxy-1-naphthoic and 6-and 7-n-alkoxy-2-naphthoic acids》. The information in the text is summarized as follows:

1-Naphthol was alkylated with NaOEt and the n-alkyl bromide or iodide by boiling 8 h. in EtOH. Distillation under reduced pressure gives the following ethers in 65-70% yield (b. p./mm. given): Me 134°/13, Et 152°/17 (m. 5°), Pr 143°/3, Bu 160°/4 (m. 19.5°), pentyl 173°/6 (m. 29.5°), hexyl 166°/4 (m. -3°), heptyl 171°/5, octyl 189°/5, nonyl 185°/4, decyl 212°/4, dodecyl 227°/3, hexadecyl 258°/1 (m. 31°), octadecyl 236°/10-2 (m. 50.5°). The 1-n-alkoxynaphthalenes were brominated with IBr in CHCl3 at 10-20°. The CHCl3 is removed and the 4-Br ethers are distilled under reduced pressure, being obtained in 65-75% yields (b. p./mm. given): Me 159°/4, Et 158°/3 (m. 48.5°), Pr 188°/8 (m. 31°), Bu 199°/5 (m. 25°), pentyl 181°/3 (m. 47.5°), hexyl 206°/5 (m. 45°). 1-n-Alkoxynaphthalenes in CS2 containing AlCl3 are treated with BrCN to form 4-n-alkoxy-1-naphthonitriles (I) in 80% yield (m. p. given): Et 88°, pentyl 60°, hexyl 62°, heptyl 54°, octyl 61°, nonyl 53°, decyl 64°, dodecyl 67°, hexadecyl 69°, octadecyl 71°. 4-n-Alkoxy-1-naphthoic acids are made from 1 g.-atom Mg turnings and 2 g. of the 1-bromonaphthalene in 25 mL. ether by refluxing 5 min. A total of 0.1 mol of the 1-bromonaphthalene in 75 mL. ether is added dropwise in 30 min. and reflux is continued 10 h. The mixture is added to ether saturated with Dry Ice. The excess CO2 is evaporated and the solution stirred with 50 mL. 17% HCl. The ether is removed and the acid washed free of MgCl2. The acids are recrystallized from glacial HOAc in 80-5% yield. Another method of forming the acids is to reflux 0.1 mol of the nitrile with 250 mL. of a solution of MeOH saturated with KOH for 15-25 h. The diluted mixture is acidified, redissolved in NaOH, and reacidified to give the following 1-carboxy analogs of I in 95-7% yields (m. p. given): Me 248°, Et 220°, Pr 203°, Bu 213.5°, pentyl 207°, hexyl 212°, heptyl 189°, octyl 183.5°, nonyl 161°, decyl 174.5°, dodecyl 147.5°, hexadecyl 136°, octadecyl 137.5°. Na 5-aminonaphthalene-1-sulfonate (70 g.) and 14 g. KCN are ground together and dry-distilled in an all-glass retort at 500-600°, the distillate is dissolved in 1.3 l. boiling 0.3N HCl, the solution is cooled and filtered, and the filtrate is neutralized with concentrated NH3 to give 22-6% 5-amino-1-naphthonitrile (II), m. 140°, b2-3 187-93°. II (0.03 mol) is dissolved in 60 mL. glacial HOAc at 80°, 60 mL. 40% H2SO4 is added with stirring, the solution is cooled to 0°, 0.06 mol NaNO2 in 30 mL. H2O is added, the solution is stirred at 0-5° until it clears, urea is used to destroy the excess NO2-, the solution is immediately added dropwise with stirring to a boiling solution of 180 mL. 40% H2SO4 in 30 min. refluxing is continued 1 h., the mixture is cooled, 300 mL. H2O is added, the solution is extracted with ether, the ether is extracted with N NaOH, and the basic extract is acidified to give 67% 5-hydroxy-1-naphthonitrile (III), m. 204-6°. After 8.4 g. III is refluxed with 50 g. KOH in 100 mL. H2O for 4-5 h., acidification gives 90% 5-hydroxy-1-naphthoic acid (IV), m. 238°; acetyl derivative, m. 204-5°. IV is methylated with Me sulfate at 40-50° in basic solution (the ester, which is a byproduct, is removed by refluxing with MeOH-KOH). The product is 5-methoxy-1-naphthoic acid (V), m. 232.5°. The following homologs of V are similarly prepared (alkyl and m. p. given): Et 201°, Pr 189°, Bu 172°, pentyl 143°, hexyl 154°, heptyl 135.5°, octyl 142.5°, nonyl 143°, decyl 137°, dodecyl 125°, hexadecyl 117.5°, octadecyl 122°. 2-Naphthol (1 mol) in 400 mL. glacial HOAc is brominated at room temperature and the resulting 1,6-dibromo-2-naphthol is reduced with mossy Sn at reflux to give 90-100% 6-bromo-2-naphthol (VI), m. 123-7°. The VI is treated with Me sulfate in alkali to give 60-70% 2-bromo-6-methoxynaphthalene (VII), m. 106-7°, b. 189-99°/20 mm. 6-Methoxy-2-naphthoic acid is formed from VII by the method of Fries and Schimmelschmidt (C.A. 20, 1616), m. 206° in 50-5% yield. AcCl treated with VII in the presence of AlCl3 in PhNO2 and distillation gives 5% 2-acetyl-6-methoxynaphthalene (VIII), m. 104-5°, b. 165-70°/3-4 mm. VIII (50 g.) in 350 mL. dioxane, is treated with NaOBr (from 140 g. NaOH, 600 mL. H2O, and 50 mL. Br) dropwise for 30 min. at 35-40° (reaching 50-5° at the end), excess Br is destroyed, 2 l. H2O is added, dioxane and CHBr3 are removed by steam distillation, and the solution is filtered and acidified with concentrated HCl to give 70-5% 6-methoxy-2-naphthoic acid (IX), m. 205-6°. IX (8 g.) is heated 2.5 h. with 35 mL. AcOH, 35 mL. 48% HBr, and 20 mL. glacial HOAc to give 6-hydroxy-2-naphthoic acid (X), m. 250° (Bz derivative, m. 257°; Ac derivative, m. 228°; phenylsulfonyl derivative, m. 228.5°). X was alkylated in 85-90% yield. The following 6-alkoxy analog of X were prepared (alkyl and m. p. given): Me 206°, Et 213°, Pr 208°, Bu 198°, pentyl 179.5°, hexyl 147°, heptyl 163°, octyl 161.5°, nonyl 147.5°, decyl 139°, dodecyl 119°, hexadecyl 107°, octadecyl 114.6°, isopentylnaphthoic acid 194.6°, 3,5,5-trimethylhexyl 170°. 7-Amino-2-naphthonitrile m. 197°. 7-Hydroxy-2-naphthonitrile, m. 186.5°. 7-Hydroxy-2-naphthoicacid m. 269-70°. 7-n-Octyloxy-2-naphthoic acid m. 142.5°, sublimes 170°/2-3 mm. 7-n-Hexadecyloxy-2-naphthoic acid m. 138°. The results came from multiple reactions, including the reaction of 5-Amino-1-naphthonitrile(cas: 72016-73-0Safety of 5-Amino-1-naphthonitrile)

5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime. Primary amines having a tertiary alkyl group (R3CNH2) are difficult to prepare with most methods but are made industrially by the Ritter reaction. In this method a tertiary alcohol reacts with hydrogen cyanide (HCN) in the presence of a concentrated strong acid; a formamide, RNH―CHO, is formed first, which then undergoes hydrolysis.Safety of 5-Amino-1-naphthonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Nguyen, Thuy; Gamage, Thomas F.; Finlay, David B.; Decker, Ann M.; Langston, Tiffany L.; Barrus, Daniel; Glass, Michelle; Li, Jun-Xu; Kenakin, Terry P.; Zhang, Yanan published an article in Journal of Medicinal Chemistry. The title of the article was 《Development of 3-(4-Chlorophenyl)-1-(phenethyl)urea Analogues as Allosteric Modulators of the Cannabinoid Type-1 Receptor: RTICBM-189 is Brain Penetrant and Attenuates Reinstatement of Cocaine-Seeking Behavior》.Formula: C8H6BrN The author mentioned the following in the article:

We have shown that CB1 receptor neg. allosteric modulators (NAMs) attenuated the reinstatement of cocaine-seeking behaviors in rats. In an effort to further define the structure-activity relationships and assess the druglike properties of the 3-(4-chlorophenyl)-1-(phenethyl)urea-based CB1 NAMs that we recently reported, we introduced substituents of different electronic properties and sizes to the phenethyl group and evaluated their potency in CB1 calcium mobilization, cAMP, and GTPγS assays. We found that 3-position substitutions such as Cl, F, and Me afforded enhanced CB1 potency, whereas 4-position analogs were generally less potent. The 3-chloro analog (31, RTICBM-189)(I) showed no activity at >50 protein targets and excellent brain permeation but relatively low metabolic stability in rat liver microsomes. Pharmacokinetic studies in rats confirmed the excellent brain exposure of 31 with a brain/plasma ratio Kp of 2.0. Importantly, i.p. administration of 31 significantly and selectively attenuated the reinstatement of the cocaine-seeking behavior in rats without affecting locomotion. In addition to this study using 2-(3-Bromophenyl)acetonitrile, there are many other studies that have used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Formula: C8H6BrN) was used in this study.

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.Formula: C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Joy, F.; Peter, F.; Gokul, P. C.; Nizam, A.; Chinnam, S. published an article in 2022. The article was titled 《UV-Promoted Metal- and Photocatalyst-Free Direct Conversion of Aromatic Aldehydes to Nitriles》, and you may find the article in Russian Journal of Organic Chemistry.Quality Control of 4-Fluorobenzonitrile The information in the text is summarized as follows:

An efficient, simple and catalyst-free UV-induced functional group transformation of aromatic aldehydes to nitriles was reported. The developed strategy delivered various functionalized aromatic nitriles with high yields and purity. The UV irradiation activated the carbonyl group of aldehydes and lead to the formation of aldoxime intermediate, further resulting in the generation of nitriles. The striking highlights of the reported methodol. were simple reaction conditions, good yields, UV-promoted transformation and catalyst-free synthesis. Due to the above-mentioned advantages, the methodol. provided a hand towards environmentally friendly chem. synthesis. In the experiment, the researchers used many compounds, for example, 4-Fluorobenzonitrile(cas: 1194-02-1Quality Control of 4-Fluorobenzonitrile)

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Lu, Wen-Xiu; Xing, Jian; Sun, Yijia; Huang, Qinge; Deng, Zhenwei; Mao, Jian-Gang published their research in Organic & Biomolecular Chemistry in 2021. The article was titled 《Palladium-catalyzed and alcohol-enabled transformation to synthesize benzocyclic ketones》.Formula: C7H4BrN The article contains the following contents:

A highly effective palladium-catalyzed and alc.-promoted transformation of nitriles to synthesize benzocyclic ketones was described. It provided a straightforward access to potentially valuable indanone compounds in high yields in the presence of alc. It avoided the usage of carbon monoxide or an addnl. hydrolysis procedure. In the part of experimental materials, we found many familiar compounds, such as 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. 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.Formula: C7H4BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts