Month: October 2022

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

The author of 《Electrochemical Reductive Smiles Rearrangement for C-N Bond Formation》 were Chang, Xihao; Zhang, Qinglin; Guo, Chang. And the article was published in Organic Letters in 2019. Safety of 4-Bromo-2-fluorobenzonitrile The author mentioned the following in the article:

A conceptually new and synthetically valuable radical Smiles rearrangement reaction is reported under undivided electrolytic conditions. This protocol employs an entirely new strategy for the electrochem. radical Smiles rearrangement. Remarkably, an amidyl radical generated from the cleavage of the N-O bond under reductive electrolytic conditions plays a crucial role in this transformation. Various hydroxylamine derivatives bearing different substituents are suitable in this electrochem. transformation, furnishing the corresponding amides in up to 86% yield. In the part of experimental materials, we found many familiar compounds, such as 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Safety 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.Safety 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

《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

《Discovery and characterization of a novel perylenephotoreductant for the activation of aryl halides》 was written by Li, Min; Li, Jia; Guo, Baodang; Liu, Xuanzhong; Yuan, Zhenbo; Wu, Yawen; Yin, Huimin; Huang, Shuping; Zhang, Yan; Rao, Yijian. Related Products of 105942-08-3 And the article was included in Journal of Catalysis in 2021. The article conveys some information:

To develop a photocatalyst with catalytical activity for substrates with low reactivities is always highly desired. Herein, based on the principle of structure-property relationships, we rationally designed the natural product cercosporin, the naturally occurring perylenequinonoid pigment, to develop a novel organic perylenephotoreductant, hexacetyl reduced cercosporin (HARCP), through structural manipulation. Compared with cercosporin, HARCP shows prominent electrochem. and photophys. characteristics with greatly improved photoreductive activity, fluorescence lifetime and fluorescence quantum yield. These properties allowed HARCP as a powerful photoreductant to efficiently realize a series of benchmark reactions, including photoreduction, alkoxylation and hydroxylation to construct C-H and C-O bonds using aryl halides as substrates under mild conditions, all of which have never been achieved by the same photocatalyst. Thus, this study well supports the notion that the principle between structural manipulation and photocatalytic activity is of great significance to design customized photocatalysts for photoredox chem. The results came from multiple reactions, including the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Related Products of 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.Related Products 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

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

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

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

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,Akkoc, Mitat; Bugday, Nesrin; Altin, Serdar; Ozdemir, Ismail; Yasar, Sedat published an article in Catalysis Letters. The title of the article was 《Highly Active Fe3O4@SBA-15@NHC-Pd Catalyst for Suzuki-Miyaura Cross-Coupling Reaction》.Computed Properties of C7H4BrN The author mentioned the following in the article:

A novel Pd-NHC functionalized magnetic Fe3O4@SBA-15@NHC-Pd catalyst was synthesized and used as an efficient heterogeneous catalyst in the Suzuki-Miyaura C-C bond formation reactions. The Fe3O4@SBA-15@NHC-Pd characterized by X-Ray Diffraction (XRD), XPS, Fourier Transform IR (FTIR) spectroscopy, SEM (SEM), Transmission Electron Microscopy (TEM), Energy Dispersive X-ray anal. (EDX), Thermogravimetric Anal. (TGA), DTA (DTA). The Inductively Coupled Plasma-Optical emission spectroscopy (ICP-OES) anal. was used to determine the exact amount of Pd (0.33 wt%) in Fe3O4@SBA-15@NHC-Pd. The TEM images of the catalyst showed the existence of palladium nanoparticles immobilized in the catalyst’s structure, while no reducing agent was used. The NHC moieties in the catalyst structure could be stabilize Pd(0) nanoparticles prevents agglomeration. The magnetic catalyst was effectively used in the Suzuki-Miyaura cross-coupling reaction of substituted phenylboronic acid derivatives with (hetero)aryl bromides in the presence of a potassium carbonate at room temperature in aqueous media and magnetic catalyst could be simply extracted from the reaction mixture by an external magnet. Different aryl bromides were converted to coupled-products Ar1Ar2 [Ar1 = Ph, 4-MeC6H4, 4-MeOC6H4, etc.; Ar2 = Ph, 2-MeC6H4, 1-naphthyl, etc.] in excellent yields with spectacular TOFs values (up to 1,960,339 h-1); in the presence of 1 mg of Fe3O4@SBA-15@NHC-Pd catalyst (contains 3.1 x 10-6 mol% Pd) at room temperature in aqueous media. After reusability experiments, it was found that this catalyst was effectively used up to ten times in the reaction with almost consistent catalytic efficiency. A decrease in the activity of the 10th reused catalyst was found as 9%. The results came from multiple reactions, including the reaction of 2-Bromobenzonitrile(cas: 2042-37-7Computed Properties of C7H4BrN)

2-Bromobenzonitrile(cas: 2042-37-7) is used as a starting material to synthesize novel benzothiophene derivatives that were found to exhibit antibacterial and antifungal activity. It is commonly employed in reactions that require an electron-rich species to carry out nucleophilic substitution (or addition) reactions.Computed Properties of C7H4BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Recommanded Product: 31938-07-5In 2013 ,《Synthesis of the Natural Product Building Block 5-(3-Bromophenyl)-4-hydroxy-5-methylhexan-2-one and its Chiral Characterization by Using Chiroptical Spectroscopy》 appeared in ChemPhysChem. The author of the article were De Gussem, Ewoud; Cornelus, Jelle; Pieters, Sam; Van den Bossche, Dries; Van der Eycken, Johan; Herrebout, Wouter; Bultinck, Patrick. The article conveys some information:

The absolute configuration of 5-(3-bromophenyl)-4-hydroxy-5-methylhexan-2-one, an intermediate in the synthesis of various natural products, is assigned by using vibrational CD (VCD), electronic CD (ECD), and ORD. Exptl. spectra were compared to d. functional theory (DFT) calculations of the mol. with known configuration. These three techniques independently confirm that the absolute configuration is (S)-5-(3-bromophenyl)-4-hydroxy-5-methylhexan-2-one, thus enabling us to assign the absolute configuration with high reliability. The reliability of the VCD anal. was assessed quant. by using the CompareVOA program. In cases in which the agreement between theory and experiment was very good, a value of 10 cm-1 for the triangular weighting function gave a more-realistic discriminative power between enantiomers than the default value of 20 cm-1. The results came from multiple reactions, including the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Recommanded Product: 31938-07-5)

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.Recommanded Product: 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts