Tag: 100-200

In 2022,Yang, Yongliang; Luo, Na; Lin, Shiyun; Yao, Huan; Cai, Yaqi published an article in ACS Catalysis. The title of the article was 《Cyano Substituent on the Olefin Linkage: Promoting Rather than Inhibiting the Performance of Covalent Organic Frameworks》.Recommanded Product: 17201-43-3 The author mentioned the following in the article:

It is generally believed that the electron-withdrawing cyano group in the olefin linkage would inhibit the stability and π-conjugation of covalent organic frameworks (COFs), which raises concerns about their optoelectronic properties. However, the structure-activity relationship between the structure of olefin linkages and properties of COFs is still inconclusive. In this work, imine-, vinylene-, and acrylonitrile-linked COFs with identical triphenyltriazine building blocks were designed and synthesized. Our work demonstrated that construction of acrylonitrile linkages not only enhanced the chem. stability and photostability but also led to remarkable optoelectronic properties with a record fluorescence quantum yield of 35.37% in the solid state. Further, the acrylonitrile linkage endows TTAN-COF/Pt NPs with superior and durable photocatalytic activity in both the hydrogen evolution reaction (11.94 mmol g-1 h-1; BET surface area, 739.28 m2 g-1) and aerobic oxidation reaction. This work demonstrates that the acrylonitrile linkage can significantly enhance the optoelectronic properties and photocatalytic activities of COFs compared with the highly π-conjugated vinylene linkage, providing a valuable reference for the design of optoelectronic functional materials. In the experiment, the researchers used 4-Cyanobenzyl bromide(cas: 17201-43-3Recommanded Product: 17201-43-3)

4-Cyanobenzyl bromide(cas: 17201-43-3) is used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile. It is also useful in the preparation of 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile by reaction with 2H-tetrazole in the presence of potassium hydroxide.Recommanded Product: 17201-43-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Wang, Qiao-Lin; Sun, Zhaozhao; Huang, Huawen; Mao, Guojiang; Deng, Guo-Jun published an article in Green Chemistry. The title of the article was 《Stoichiometric couplings of methylarenes through visible-light-induced bromo radical formation from aryl halides》.Application In Synthesis of 2-Bromobenzonitrile The author mentioned the following in the article:

A visible-light/nickel dual catalyzed stoichiometric coupling of methylarenes via bromine radical-enhanced HAT was developed. Aryl bromides serve as both cross-coupling partners and bromine radical precursors. Mechanistic studies revealed that the bromine radical acts as a highly efficient HAT reagent to abstract the benzylic C(sp3)-H bond to deliver a benzylic radical and subsequently engages in Ni-catalyzed arylation couplings. The synthetic utility of this approach was further proved by its application in the late-stage arylation or benzylation of several drug-like and complex mols. in a stoichiometric manner. In the experiment, the researchers used 2-Bromobenzonitrile(cas: 2042-37-7Application In Synthesis of 2-Bromobenzonitrile)

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.Application In Synthesis of 2-Bromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhang, Jun-Qi; Liu, Jiayue; Hu, Dandan; Song, Jinyu; Zhu, Guorong; Ren, Hongjun published an article in 2022. The article was titled 《Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes》, and you may find the article in Organic Letters.Category: nitriles-buliding-blocks The information in the text is summarized as follows:

A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitriles derivatives RCH(R1)CN [R = Ph, 4-ClC6H4, 4-NO2C6H4, etc.; R1 = H, Me, 2-ClC6H4, etc.] was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope and broad functional group tolerance. Significantly, in this reaction, aqueous ammonia offers “”N”” source for the “”CN”” reagent and entirely avoided the use of toxic cyanating regents or metal catalysis. Hence, provided a green and alternative method for the synthesis of arylacetonitriles. The results came from multiple reactions, including the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Category: nitriles-buliding-blocks)

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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhou, Quan-Quan; Zou, You-Quan; Kar, Sayan; Diskin-Posner, Yael; Ben-David, Yehoshoa; Milstein, David published an article in 2021. The article was titled 《Manganese-Pincer-Catalyzed Nitrile Hydration, α-Deuteration and α-Deuterated Amide Formation via Metal Ligand Cooperation》, and you may find the article in ACS Catalysis.Related Products of 31938-07-5 The information in the text is summarized as follows:

A simple and efficient system for the hydration and α-deuteration of nitriles to form amides RC(O)NH2 [R = Me, Bn, 4-FC6H4, etc.] and α-deuterated nitriles R1CD2CN [R1 = PhCH2CH2, 3-MeC6H4, 3-pyridyl, etc.] catalyzed by a single pincer complex of the earth-abundant manganese capable of metal-ligand cooperation is reported. The deuteration reaction is selective and tolerates a wide range of functional groups, giving the corresponding amides in moderate to good yields. Changing the solvent from tert-butanol to toluene and using D2O results in formation of α-deuterated nitriles in high selectivity. Moreover, α-deuterated amides can be obtained in one step directly from nitriles and D2O in THF. Preliminary mechanistic studies suggest the transformations contributing toward activation of the nitriles via a metal-ligand cooperative pathway, generating the manganese ketimido and enamido pincer complexes as the key intermediates for further transformations. The results came from multiple reactions, including the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Related Products of 31938-07-5)

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.Related Products of 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Photo-Ni-Dual-Catalytic C(sp2)-C(sp3) Cross-Coupling Reactions with Mesoporous Graphitic Carbon Nitride as a Heterogeneous Organic Semiconductor Photocatalyst》 was published in ACS Catalysis in 2020. These research results belong to Khamrai, Jagadish; Ghosh, Indrajit; Savateev, Aleksandr; Antonietti, Markus; Koenig, Burkhard. Application In Synthesis of 4-Bromobenzonitrile The article mentions the following:

The synergistic combination of a heterogeneous organic semiconductor mesoporous graphitic carbon nitride (mpg-CN) and a homogeneous nickel catalyst with visible-light irradiation at room temperature affords the C(sp2)-C(sp3) cross-coupling of aryl halides and potassium alkyl trifluoroborates by single electron transmetallation. Like the homogeneously catalyzed protocol, the reaction is compatible with a variety of functional groups including electron-donating and electron-withdrawing aryl and heteroaryl moieties. Moreover, this protocol allows the installation of allyl groups onto (hetero)arenes, enlarging the scope of the method. The heterogeneous mpg-CN photocatalyst is easily recovered from the reaction mixture and reused several times, paving the way for larger-scale industrial applications of this type of photocatalytic bond-forming reactions. In the part of experimental materials, we found many familiar compounds, such as 4-Bromobenzonitrile(cas: 623-00-7Application In Synthesis of 4-Bromobenzonitrile)

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,Application In Synthesis 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

In 2019,ChemCatChem included an article by Ichitsuka, Tomohiro; Suzuki, Naoto; Sairenji, Masaki; Koumura, Nagatoshi; Onozawa, Shun-ya; Sato, Kazuhiko; Kobayashi, Shu. Recommanded Product: 4-Bromobenzonitrile. The article was titled 《Readily Available Immobilized Pd Catalysts for Suzuki-Miyaura Coupling under Continuous-flow Conditions》. The information in the text is summarized as follows:

A consistent method was developed for evaluating the catalytic performance of com. available immobilized Pd-catalysts under continuous-flow conditions for the preparation of biaryls via Suzuki-Miyaura coupling of aryl bromides with arylboronic acids. Monitoring of the change in turnover frequency over time under excess substrate loading conditions revealed the limitation of these catalysts. In addition to this study using 4-Bromobenzonitrile, there are many other studies that have used 4-Bromobenzonitrile(cas: 623-00-7Recommanded Product: 4-Bromobenzonitrile) was used in this study.

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: 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

In 2014,Al Otaibi, Ahmed; Gordon, Christopher P.; Gilbert, Jayne; Sakoff, Jennette A.; McCluskey, Adam published 《The influence of ionic liquids on the Knoevenagel condensation of 1H-pyrrole-2-carbaldehyde with phenyl acetonitriles – cytotoxic 3-substituted-(1H-pyrrol-2-yl)acrylonitriles》.RSC Advances published the findings.Name: 2-(3-Bromophenyl)acetonitrile The information in the text is summarized as follows:

The Knoevenagel condensation of a series of substituted Ph acetonitriles with 1H-pyrrole-2-carbaldehyde was examined in seven 1-butyl-3-methylimidazolium based ionic liquids and three protic ionic liquids Of these [BMIM][Br] and [BMIM][OH], with catalytic piperidine, proved most efficient affording 3-substituted-(1H-pyrrol-2-yl)acrylonitriles 3-17 in good to excellent yields (98%) while utilization of the protic ionic liquid Pr ammonium nitrate resulted in reduced yields (0-66%). Screening of the 3-substituted-(1H-pyrrol-2-yl)acrylonitriles analogs 3-17 against a panel of 11 cancer cell lines and one normal cell line allowed the identification of a series of compounds with broad spectrum cytotoxicity, but more interestingly a significant degree of MCF-7 breast cancer cell line specificity was evident with 6 (7 to >25 fold) and 13 (5.7 to >80 fold). Other analogs show high level of efficacy against specific cell lines with 10 showing excellent activity against MCF-7 (GI50 = 1.7 μM) and A431 (GI50 = 2.8 μM) cell lines. The most promising of the compounds identified herein were the 4-CF3 substituted 10 and the 3,4-dichloro substituted 13 with excellent activities against MCF-7 and A431 cell lines. The 3,4-dichloro-13 was a 0.56 μM potent inhibitor of MCF-7 cell growth. The results came from multiple reactions, including the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Name: 2-(3-Bromophenyl)acetonitrile)

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.Name: 2-(3-Bromophenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2012,Huang, Liping; Liu, Yang; Xie, Fuchun; Hu, Youhong published 《An Organic Molecule Modulated Chemoselective Cyclization of Alkynyl Nitriles Tethered to 2-Alkyl Substituted Chromones with Multireactive Sites》.Organic Letters published the findings.Synthetic Route of C8H6BrN The information in the text is summarized as follows:

A small organic mol. phenylacetonitrile promoted chemoselective cyclization of (chromen-3-yl)alkynylnitriles to generate a novel tetracyclic or tricyclic chromone scaffold has been discovered. Importantly, the phenylacetonitrile serves as an anion transfer reagent changing the normal reaction of the substrate. In the experiment, the researchers used 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 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione or a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands.Synthetic Route of C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wang, Qile; Zheng, Nan published their research in Organic Letters on December 20 ,2019. The article was titled 《Difunctionalization of Cyclopropyl Amines with N-Iodosuccinimide (NIS) or in Situ Formed Cyanogen Iodide (ICN)》.Application of 1019607-55-6 The article contains the following contents:

Herein, a 1,3-difunctionalization of cyclopropylamines that serve as a π nucleophile in a two-electron (2e) SN2-like ring opening pathway is described. N-Iodosuccinimide (NIS) or in situ generated cyanogen iodide (ICN) is employed as electrophilic iodinating reagents in conjunction with TMSCN or succinimide to furnish multiple pairs of functional groups disposed in a 1,3-manner. This 2e ring opening manifold overcomes the constraint of previously reported 1e protocol as demonstrated by successful activation of monocyclic tertiary cyclopropylamines. In the experiment, the researchers used many compounds, for example, 4-(Cyclopropylamino)benzonitrile(cas: 1019607-55-6Application of 1019607-55-6)

4-(Cyclopropylamino)benzonitrile(cas: 1019607-55-6) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Application of 1019607-55-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kenari, Marziyeh E.; Putman, Joshua I.; Singh, Ravi P.; Fulton, Brandon B.; Phan, Huy; Haimour, Reem K.; Tse, Key; Berthod, Alain; Lovely, Carl J.; Armstrong, Daniel W. published their research in Molecules in 2021. The article was titled 《Enantiomeric separation of new chiral azole compounds》.HPLC of Formula: 1194-02-1 The article contains the following contents:

Twelve new azole compounds (rec/R/S)-I (Ar = Ph, Bn, Bz, allyl, 3,5-bis(trifluoromethyl)phenyl; R = 2,5-dioxo-1-phenylpyrrolidin-3-yl, 2-ethoxy-1-hydroxy-2-oxoethyl), (rec/R/S)-II (R1 = Ph, 4-chlorophenyl, 4-fluorophenyl, 4-methoxyphenyl) and (rec/R/S)-III were synthesized through an ene reaction involving methylidene heterocycles IV and V and N-phenylmaleimide, producing four oxazoles II (R = 2,5-dioxo-1-phenylpyrrolidin-3-yl), five thiazoles I (R = 2,5-dioxo-1-phenylpyrrolidin-3-yl), and one pyridine derivative, III and Et glyoxylate for an oxazole II (R = 2-ethoxy-1-hydroxy-2-oxoethyl) and a thiazole compd I (R = 2-ethoxy-1-hydroxy-2-oxoethyl). The twelve azoles I, II and III have a stereogenic center in their structure. Hence, a method to sep. the enantiomeric pairs, must be provided if any further study of chem. and pharmacol. importance of these compounds is to be accomplished. Six chiral stationary phases were assayed: four were based on macrocyclic glycopeptide selectors and two on linear carbohydrates, i.e., derivatized maltodextrin and amylose. The enantiomers of the entire set of new chiral azole compounds I, II and III were separated using three different mobile phase elution modes: normal phase, polar organic, and reversed phase. The most effective chiral stationary phase was the MaltoShell column, which was able to sep. ten of the twelve compounds I, II and III in one elution mode or another. Structural similarities in the newly synthesized oxazoles II provided some insights into possible chiral recognition mechanisms. The results came from multiple reactions, including the reaction of 4-Fluorobenzonitrile(cas: 1194-02-1HPLC of Formula: 1194-02-1)

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.HPLC of Formula: 1194-02-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts