Month: October 2022

In 2018,Angewandte Chemie, International Edition included an article by Xue, Fei; Hayashi, Tamio. Name: 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile. The article was titled 《Asymmetric Synthesis of Axially Chiral 2-Aminobiaryls by Rhodium-Catalyzed Benzannulation of 1-Arylalkynes with 2-(Cyanomethyl)phenylboronates》. The information in the text is summarized as follows:

In the presence of [RhCl(coe)]2 and nonracemic bicyclooctadienecarboxamide I, internal aryl alkynes such as 1-(1-propynyl)naphthalene with ortho-substituted aryl moieties underwent regioselective and enantioselective cyclization reactions with o-(pinacolboronato)phenylacetonitriles mediated by K3PO4 in aqueous 1,4-dioxane to yield nonracemic biarylamines such as binaphthylamine II with stereogenic axes in 72-97% ee (all but one compound formed in >90% ee). In the experiment, the researchers used many compounds, for example, 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile(cas: 325141-71-7Name: 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile)

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. Name: 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Signatures of glass transition in partially ordered phases》 were Jasiurkowska-Delaporte, Malgorzata; Juszynska, Ewa; Kolek, Lukasz; Krawczyk, Jan; Massalska-Arodz, Maria; Osiecka, Natalia; Rozwadowski, Tomasz. And the article was published in Liquid Crystals in 2013. Category: nitriles-buliding-blocks The author mentioned the following in the article:

Features of glass transition in liquid crystalline nematic and smectic E, B and IA phases of selected materials observed by means of the polarising microscopy and Fourier transform IR spectroscopy (FTIR) are reported. Evolution of cracking in the glass and a coincidence of its disappearance temperature with the glass transition temperature (Tg) on heating is shown and discussed in the context of processes that occur in the glass. The shape of temperature dependencies of absorption bands is shown as the signature of the glass transition. In the part of experimental materials, we found many familiar compounds, such as 4-Cyano-3-fluorophenyl 4-butylbenzoate(cas: 86776-52-5Category: nitriles-buliding-blocks)

4-Cyano-3-fluorophenyl 4-butylbenzoate(cas: 86776-52-5) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2014,Mentese, E.; Yilmaz, F.; Karaali, N.; Ulker, S.; Kahveci, B. published 《Rapid synthesis and lipase inhibition activity of some new benzimidazole and perimidine derivatives》.Russian Journal of Bioorganic Chemistry published the findings.Product Details of 31938-07-5 The information in the text is summarized as follows:

Synthesis of new series of some benzimidazoles I (R = 3,4-Cl2C6H3CH2, 2,4-Cl2C6H3CH2, 2,6-Cl2C6H3CH2, etc.), bisbenzimidazoles II and perimidine derivatives III via microwave technique, which, leads to the good product yields and short reaction times is presented. These compounds were screened for their lipase inhibition activity. All compounds were evaluated with regard to pancreatic lipase activity, and some of the 2-substituted perimidines, bisperimidine and bisbenzimidazole derivatives showed lipase inhibition at various concentrations In the experimental materials used by the author, we found 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Product Details 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.Product Details of 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2017,Cui, Jing; Peng, Xia; Gao, Dingding; Dai, Yang; Ai, Jing; Li, Yingxia published 《Optimization of 1H-indazol-3-amine derivatives as potent fibroblast growth factor receptor inhibitors》.Bioorganic & Medicinal Chemistry Letters published the findings.HPLC of Formula: 105942-08-3 The information in the text is summarized as follows:

Fibroblast growth factor receptor (FGFR) is a potential target for cancer therapy because of its critical role in promoting cancer formation and progression. In a continuing effort to improve the cellular activity of hit compound 4-(4-ethylpiperazin-1-yl)-N-[6-(2-fluoro-3-methoxyphenyl)-1H-indazol-3-yl]benzamide bearing an indazole scaffold, which was previously discovered, several compounds harnessing fluorine substituents I [R1 = H, F; R2 = H, F; R3 = H, F; R4 = H, F; R5 = H, F; R6 = H, F; X = [2-(dimethylamino)ethyl](methyl)aminyl, (3R,5S)-3,5-dimethylpiperazin-1-yl, 4-methyl-1,4-diazepan-1-yl, etc.] were designed, synthesized and biol. evaluated. Besides, the region extended out to the ATP binding pocket toward solvent was also explored. Among them, compound I [R1 = R2 = R3 = R4 = R5 = H; R6 = F; X = 4-ethylpiperazin-1-yl] containing 2,6-difluoro-3-methoxyphenyl residue exhibited the most potent activities (FGFR1: less than 4.1 nM, FGFR2: 2.0 ± 0.8 nM). More importantly, compound I [R1 = R2 = R3 = R4 = R5 = H; R6 = F; X = 4-ethylpiperazin-1-yl] showed an improved antiproliferative effect against KG1 cell lines and SNU16 cell lines with IC50 values of 25.3 ± 4.6 nM and 77.4 ± 6.2 nM resp. In the part of experimental materials, we found many familiar compounds, such as 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3HPLC of Formula: 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.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

The author of 《Triphenylbismuth Dichloride-Mediated Conversion of Thioamides to Nitriles》 were Gopi, Elumalai; Gravel, Edmond; Doris, Eric. And the article was published in European Journal of Organic Chemistry in 2019. Related Products of 1194-02-1 The author mentioned the following in the article:

Thioamides RC(S)NH2 (R = 4-BrC6H4, Ph, 1-naphthyl, pyridin-4-yl, etc.) were efficiently converted to nitriles RCN using the pentavalent triphenylbismuth dichloride in combination with triethylamine. The reaction involved the dehydrosulfurization of primary thioamides to afford substituted aromatic or aliphatic nitriles in good to excellent yields. The process was also successfully extended to the synthesis of cyanamides R1XCN (R1 = Ph, 2-methoxyphenyl; X = NH, NMe) starting from the corresponding thioureas R1XC(S)NH2 and of thiocyanates R1XCN (R1 = 3-methoxyphenyl; X = S) from dithiocarbamates R1XC(S)NH2. In addition to this study using 4-Fluorobenzonitrile, there are many other studies that have used 4-Fluorobenzonitrile(cas: 1194-02-1Related Products of 1194-02-1) was used in this study.

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.Related Products of 1194-02-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Dual Catalytic Strategy for Forging sp2-sp3 and sp3-sp3 Architectures via β-Scission of Aliphatic Alcohol Derivatives》 was published in Journal of the American Chemical Society in 2020. These research results belong to Cong, Fei; Lv, Xin-Yang; Day, Craig S.; Martin, Ruben. Product Details of 105942-08-3 The article mentions the following:

A dual platform for forging sp2-sp3 and sp3-sp3 carbon bonds via catalytic β-scission of aliphatic alc. derivatives with both aryl and alkyl halides is disclosed [e.g., I + p-(F3C)C6H4Br → II (84%, 77% isolated) in presence of photocatalyst, Hantzsch ester under blue LED irradiation with Ni/(4,4′-di-tert-butyl-2,2′-bipyridyl)]. This protocol is distinguished by its wide substrate scope and broad applicability, even in the context of late-stage functionalization. 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,
Nitriles – Chemistry LibreTexts

《Microfluidic electrochemistry for single-electron transfer redox-neutral reactions》 was written by Mo, Yiming; Lu, Zhaohong; Rughoobur, Girish; Patil, Prashant; Gershenfeld, Neil; Akinwande, Akintunde I.; Buchwald, Stephen L.; Jensen, Klavs F.. Category: nitriles-buliding-blocks And the article was included in Science (Washington, DC, United States) in 2020. The article conveys some information:

Electrochem. offers opportunities to promote single-electron transfer (SET) redox-neutral chemistries similar to those recently discovered using visible-light photocatalysis but without the use of an expensive photocatalyst. Herein, the authors introduce a microfluidic redox-neutral electrochem. (μRN-eChem) platform that has broad applicability to SET chem., including radical-radical cross-coupling, Minisci-type reactions, and Ni-catalyzed C(sp2)-O cross-coupling. The cathode and anode simultaneously generate the corresponding reactive intermediates, and selective transformation is facilitated by the rapid mol. diffusion across a microfluidic channel that outpaces the decomposition of the intermediates. μRN-eChem was shown to enable a two-step gram-scale electrosynthesis of a nematic liquid crystal compound, demonstrating its practicality.4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Category: nitriles-buliding-blocks) was used in this study.

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Enantioselective Three-Component Fluoroalkylarylation of Unactivated Olefins through Nickel-Catalyzed Cross-Electrophile Coupling》 was written by Tu, Hai-Yong; Wang, Fang; Huo, Liping; Li, Yuanbo; Zhu, Shengqing; Zhao, Xian; Li, Huan; Qing, Feng-Ling; Chu, Lingling. Category: nitriles-buliding-blocks And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

A nickel-catalyzed, enantioselective, three-component fluoroalkylarylation of unactivated alkenes with aryl halides and perfluoroalkyl iodides has been described. This cross-electrophile coupling protocol utilizes a chiral nickel/BiOx system as well as a pendant chelating group to facilitate the challenging three-component, asym. difunctionalization of unactivated alkenes, providing direct access to valuable chiral β-fluoroalkyl arylalkanes with high efficiency and excellent enantioselectivity. The mild conditions allow for a broad substrate scope as well as good functional group toleration. Thus, e.g., allylic ester I + 5-bromo-2-(trifluoromethyl)pyrimidine + IC4F9 → II (87%, 94:6 er). In the experiment, the researchers used 4-Bromobenzonitrile(cas: 623-00-7Category: nitriles-buliding-blocks)

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

Ibis, Kubra; Nalbat, Esra; Caliskan, Burcu; Kahraman, Deniz Cansen; Cetin-Atalay, Rengul; Banoglu, Erden published an article in 2021. The article was titled 《Synthesis and biological evaluation of novel isoxazole-piperazine hybrids as potential anti-cancer agents with inhibitory effect on liver cancer stem cells》, and you may find the article in European Journal of Medicinal Chemistry.Product Details of 17201-43-3 The information in the text is summarized as follows:

A series of isoxazole-piperazine analogs I (R = 2-Me, 4-Cl, 3-CN, etc.) and II (R1 = 2-Me, 3-Me, 2-F, 3-F; R2 = ((4-(4-(trifluoromethyl)benzyl)piperazin-1-yl), (4-(furan-2-carbonyl)piperazin-1-yl), (1-benzylpiperidin-4-yl)amino), etc.) were prepared, screened for their antiproliferative potential against hepatocellular carcinoma (HCC; Huh7/Mahlavu) and breast (MCF-7) cancer cells and demonstrated potent to moderate cytotoxicity with IC50 values in the range of 0.09-11.7μM. Further biol. studies with I (R1 = H) and II (R = 3-F; X = (4-(4-(trifluoromethyl)benzyl)piperazin-1-yl)) in HCC cells have shown that both compounds induced G1 or G2/M arrests resulting in apoptotic cell death. Subsequent anal. of proteins involved in cell cycle progression as well as proliferation of HCC cells revealed that these 2 compounds may affect cellular survival pathways differently depending on the mutation profiles of cells (p53 and PTEN) and epidermal/mesenchymal characteristics. Lastly, authors have demonstrated the potential anti-stemness properties of these compounds was demonstrated in which the proportion of liver CSCs in Huh7 cells (CD133+/EpCAM+) were significantly reduced by I (R1 = H) and II (R = 3-F; X = (4-(4-(trifluoromethyl)benzyl)piperazin-1-yl)). Furthermore, both compounds caused a significant reduction in expression of stemness markers, NANOG or OCT4 proteins, in Mahlavu and Huh7 cells, as well as resulted in a decreased sphere formation capacity in Huh7 cells.4-Cyanobenzyl bromide(cas: 17201-43-3Product Details of 17201-43-3) 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.Product Details of 17201-43-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 4-Cyanobenzyl bromideIn 2019 ,《A Facile Synthesis of Substituted 2-(5-(Benzylthio)-1,3,4-oxadiazol-2-yl)pyrazine Using Microwave Irradiation and Conventional Method with Antioxidant and Anticancer Activities》 appeared in Journal of Heterocyclic Chemistry. The author of the article were Patil, Sanjeev R.; Sarkate, Aniket P.; Karnik, Kshipra S.; Arsondkar, Ashish; Patil, Vrushali; Sangshetti, Jaiprakash N.; Bobade, Anil S.; Shinde, Devanand B.. The article conveys some information:

A series of novel substituted 2-(5-(benzylthio)-1,3,4-oxadiazol-2-yl)pyrazine derivatives I (X = 2,4-Cl2, 3-MeO, 4-NO2, etc.) was synthesized under microwave irradiation and conventional conditions with less reaction time with good to excellent yields. All the synthesized compounds I were screened for antioxidant and anticancer activities. Out of the 14 prepared derivatives, compounds I (X = H, 3-F) were most potent and active with antioxidant and anticancer activities, resp. Also, the developed technique was simple, easy, and less time consuming. The experimental part of the paper was very detailed, including the reaction process of 4-Cyanobenzyl bromide(cas: 17201-43-3Reference 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.Reference of 4-Cyanobenzyl bromide

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts