Month: October 2022

Talukder, Poulami; Chen, Shengxi; Roy, Basab; Yakovchuk, Petro; Spiering, Michelle M.; Alam, Mohammad P.; Madathil, Manikandadas M.; Bhattacharya, Chandrabali; Benkovic, Stephen J.; Hecht, Sidney M. published their research in Biochemistry on December 29 ,2015. The article was titled 《Cyanotryptophans as Novel Fluorescent Probes for Studying Protein Conformational Changes and DNA-Protein Interaction》.Application of 83783-33-9 The article contains the following contents:

Described herein are the syntheses and photophys. characterization of three novel cyanotryptophans, and their efficient incorporation into proteins as fluorescent probes. Photophys. characteristics indicated that each was significantly brighter and red-shifted in fluorescence emission relative to tryptophan. Each analog was used to activate a suppressor tRNA transcript and was incorporated with good efficiency into two different positions (Trp22 and Trp74) of Escherichia coli dihydrofolate reductase (ecDHFR). The Trp analogs could be monitored selectively in the presence of multiple native Trp residues in DHFR. 6-CNTrp (A) formed an efficient Förster resonance energy transfer (FRET) pair with L-(7-hydroxycoumarin-4-yl)ethylglycine (HCO, D) at position 17. Further, 6-CNTrp (A) was incorporated into two DNA binding proteins, including the Klenow fragment of DNA polymerase I and an RNA recognition motif (RRM2) of heterogeneous nuclear ribonucleoprotein L-like (hnRNP LL). Using these proteins, we demonstrated the use of FRET involving A as a fluorescence donor and benzo[g]quinazoline-2,4-(1H,3H)-dione 2′-deoxyriboside (Tf) or 4-aminobenzo[g]quinazoline-2-one 2′-deoxyriboside (Cf) as fluorescent acceptors to study the binding interaction of the Klenow fragment with duplex DNA oligomers (labeled with Tf), or the domain-specific association between hnRNP LL and the BCL2 i-motif DNA (labeled with Cf). Thus, the non-natural amino acid could be used as a FRET partner for studying protein-nucleic acid interactions. Together, these findings demonstrate the potential utility of 6-CNTrp (A) as a fluorescence donor for the study of protein conformational events. In the experimental materials used by the author, we found 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Application of 83783-33-9)

3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Application of 83783-33-9

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Photoredox catalyzed dealkylative aromatic halogen substitution with tertiary amines》 were Lipilin, Dmitry L.; Frumkin, Alexander E.; Tyurin, Alexey Y.; Levin, Vitalij V.; Dilman, Alexander D.. And the article was published in Molecules in 2021. Safety of 2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile The author mentioned the following in the article:

A reaction of aromatic halides bearing electron-withdrawing groups with tertiary amines in the presence of an iridium catalyst under blue light irradiation is described. Products of the aromatic substitution of the halide by the dialkylamino fragment are obtained. The interaction of aryl radicals with tertiary amines to generate zwitterionic radical species is believed to be the key factor responsible for the reaction efficiency. In the experiment, the researchers used many compounds, for example, 2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile(cas: 1403850-00-9Safety of 2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile)

2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile(cas: 1403850-00-9) is cyanoarene-based donor-acceptor photocatalyst developed by the Zeitler group. While this catalyst has a balanced redox profile, allowing for its use in a variety of transformations, it stands out as the most reducing catalyst of the family.Safety of 2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zheng, Shuyan; Yu, Chunhui; Shen, Zhengwu published an article in Organic Letters. The title of the article was 《Ethyl Cyanoacetate: A New Cyanating Agent for the Palladium-Catalyzed Cyanation of Aryl Halides》.Product Details of 890092-52-1 The author mentioned the following in the article:

A new Pd-catalyzed cyanation reaction has been discovered using Et cyanoacetate as the cyanating reagent. A variety of electron-rich and electron-deficient aryl halides were efficiently converted into their corresponding nitriles in good to excellent yields. In the part of experimental materials, we found many familiar compounds, such as 5-Bromo-4-methylnicotinonitrile(cas: 890092-52-1Product Details of 890092-52-1)

5-Bromo-4-methylnicotinonitrile(cas: 890092-52-1) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Product Details of 890092-52-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2015,Krishna, Patoju M.; Ramachary, Dhevalapally B.; Peesapati, Sruthi published 《Azide-acetonitrile “”click”” reaction triggered by Cs2CO3: the atom-economic, high-yielding synthesis of 5-amino-1,2,3-triazoles》.RSC Advances published the findings.Reference of 2-(3-Bromophenyl)acetonitrile The information in the text is summarized as follows:

Medicinally important 5-amino-1,2,3-triazoles e.g., I, were synthesized via Cs2CO3-catalyzed azide-acetonitrile [3 + 2]-cycloaddn reactions. Aryl azides and arylacetonitriles were employed in this transformation resulting in excellent yields with high regioselectivity. After reading the article, we found that the author used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Reference of 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.Reference of 2-(3-Bromophenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2017,Dziaduszek, J.; Dabrowski, R.; Urban, S.; Garbat, K.; Glushchenko, A.; Czuprynski, K. published 《Selected fluorosubstituted phenyltolanes with a terminal group: NCS, CN, F, OCF3 and their mesogenic and dielectric properties and use for the formulation of high birefringence nematic mixtures to GHz and THz applications》.Liquid Crystals published the findings.Computed Properties of C7H3BrFN The information in the text is summarized as follows:

Thirty laterally fluorosubstituted new 4-isothiocyanato-, 4-cyano-, 4-fluoro- and 4-(1,1,1-trifluorometoxy)-4′-(4-alkylphenyl)tolanes have been synthesized and their phase transition temperatures and enthalpies and elec. permittivity have been measured. These data have been analyzed together with data for earlier prepared similar compounds and with recently prepared analogously substituted 4″”-alkyl-terphenyls. It was shown that some di-, tri- and tetra-fluorosubstituted 4-isothiocyanato- and 4-cyano-4′-(4-alkylphenyltolanes) are very useful components for the formulation of high birefringence (Δn up to 0.5 measured at 589 nm) and large temperature range nematic mixtures for photonic applications, especially in the infra-red, GHz and THz range of electromagnetic radiation. Three ways of formulation of high birefringence mixtures were proposed. In addition to this study using 4-Bromo-2-fluorobenzonitrile, there are many other studies that have used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Computed Properties of C7H3BrFN) 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.Computed Properties of C7H3BrFN 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Organic Letters included an article by Wimmer, Alexander; Koenig, Burkhard. Name: 4-Bromobenzonitrile. The article was titled 《N-Arylation of NH-Sulfoximines via Dual Nickel Photocatalysis》. The information in the text is summarized as follows:

The pharmaceutically underexplored sulfoximine moiety has emerged as a potentially active pharmaceutical ingredient. We developed a scalable synthetic route to N-arylated sulfoximines from the resp. “”free”” NH-sulfoximines and bromoarenes. Our strategy is based on a dual nickel photocatalytic approach, is applicable for a broad scope of substrates, and exhibits a highly functional group tolerance. In addition, we could demonstrate that other sulfoximidoyl derivatives like sulfonimidamides and sulfinamides proceed smoothly under the developed reaction conditions. In the experiment, the researchers used 4-Bromobenzonitrile(cas: 623-00-7Name: 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,Name: 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,Organic Letters included an article by Nagaraju, Sakkani; Liu, Shuhua; Liu, Jinggong; Yang, Shuang; Liu, Rui; Chen, Zhizhou; Paplal, Banoth; Fang, Xinqiang. Related Products of 614-16-4. The article was titled 《Regioselectivity-Switchable Catalytic Annulations of Alkynyl α-Diketones and α-Cyanoketones》. The information in the text is summarized as follows:

Regioselectivity-switchable reactions hold irreplaceable importance in the construction of diversified architectures. In this work, Bronsted base-catalyzed regioselectivity-switchable annulations between alkynyl α-diketones and α-cyanoketones have been achieved for the first time, delivering a series of skeletally thoroughly different dihydrofurofuran and furan derivatives A range of novel transformations of the products can be realized. The work also demonstrates the unique features of alkynyl α-diketone chem., which are in sharp contrast to the current understanding of ynone-related chem. In the experimental materials used by the author, we found 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Related Products of 614-16-4)

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used to produce 2-benzoyl-3-furan-2-yl-acrylonitrile. It is an active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines.Related Products of 614-16-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Desaintjean, Alexandre; Danton, Fanny; Knochel, Paul published their research in Synthesis in 2021. The article was titled 《Preparation of Functionalized Diorganomagnesium Reagents in Toluene via Bromine or Iodine/Magnesium-Exchange Reactions》.Quality Control of 2-Bromobenzonitrile The article contains the following contents:

A wide range of polyfunctionalized di(hetero)aryl- and dialkenyl-magnesium reagents were prepared in toluene within 10 to 120 min between -78°C and 25°C via an I/Mg- or Br/Mg-exchange reaction using reagents of the general formula R2Mg (R = sBu, Mes). Highly sensitive functional groups, such as triazene or nitro, were tolerated in these exchange reactions, enabling the synthesis of various functionalized (hetero)arene and alkene derivatives after quenching with several electrophiles including allyl bromides, acyl chlorides, aldehydes, ketones and aryl iodides. In the experimental materials used by the author, we found 2-Bromobenzonitrile(cas: 2042-37-7Quality Control 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.Quality Control of 2-Bromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Xiao, Wenling; Guan, Xinqiao; Huang, Bingcheng; Ye, Qiuhao; Zhang, Tiantian; Chen, Kuizhi; Peng, Yiru; Fu, Fangmeng published an article in 2021. The article was titled 《Fluorinated dendritic silicon (IV) phthalocyanines nanoparticles: Synthesis, photoinduced intramolecular energy transfer and DNA interaction》, and you may find the article in Dyes and Pigments.Category: nitriles-buliding-blocks The information in the text is summarized as follows:

Two series of fluorinated and non-fluorinated dendritic silicon (IV) phthalocyanines with cyano/nitro/ester terminal functionalities have been synthesized. Their structures were characterized by elemental anal., FT-IR, 1H NMR and ESI-MS. The effects of fluorinated groups and terminal functionalities properties on the photophys. properties, photoinduced intermol. electron transfer and intramol. energy transfer of silicon phthalocyanines were compared. In order to endow water soluble and biocompatibility to these silicon phthalocyanines, an amphiphilic diblock copolymer polyethylene glycol monomethyl ether-polycaprolactone was used to encapsulate these silicon phthalocyanines to form fluorinated and non-fluorinated dendritic silicon phthalocyanines nanoparticles. The binding model between the fluorinated dendritic silicon phthalocyanines nanoparticles and calf thymus DNA was studied by UV-Vis and fluorescence spectroscopic method. The photocleavage DNA activities of three fluorinated dendritic silicon phthalocyanines nanoparticles were compared and the possible cleavage mechanism was proposed. In addition to this study using 4-Cyanobenzyl bromide, there are many other studies that have used 4-Cyanobenzyl bromide(cas: 17201-43-3Category: nitriles-buliding-blocks) was used in this study.

4-Cyanobenzyl bromide(cas: 17201-43-3) is a white solid. Its melting point is 113-117°C, and flash point is 125.1°C. It is insoluble in water at 20°C. It is stable under normal temperatures and pressures. It should be stored at 0-5°C.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kaloglu, Murat; Kaloglu, Nazan; Ozdemir, Ismail published an article in 2021. The article was titled 《Palladium-PEPPSI-NHC Complexes Bearing Imidazolidin-2-Ylidene Ligand: Efficient Precatalysts for the Direct C5-Arylation of N-Methylpyrrole-2-Carboxaldehyde》, and you may find the article in Catalysis Letters.Reference of 2-Bromobenzonitrile The information in the text is summarized as follows:

The Pd-catalyzed direct arylation of pyrroles is an important research field for organic synthesis and catalysis chem. However, imidazolidin-2-ylidene based Pd-NHC complexes (NHC=N-heterocyclic carbene) have not yet been employed as catalysts for the direct C5 mono-arylation of C2-substituted N-methylpyrrole derivatives with aryl halides. Therefore, a report on the synthesis and characterization of new 1,3-bis(substituted benzyl) imidazolinium salts as carbene precursors, and their corresponding Pd-PEPPSI-NHC type complexes (PEPPSI=Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation) has been described. The catalytic properties of these complexes have been evaluated in the direct C5 mono-arylation of N-methylpyrrole-2-carboxaldehyde with a wide variety of (hetero)aryl halides. This environmentally attractive procedure has also been found to be tolerant to a wide variety of functional groups on the aryl halides such as formyl, acetyl, nitrile, fluoro or trifluoromethyl, and good yields have been obtained in presence of 1 mol% catalyst loading at 120°. The results came from multiple reactions, including the reaction of 2-Bromobenzonitrile(cas: 2042-37-7Reference of 2-Bromobenzonitrile)

2-Bromobenzonitrile(cas: 2042-37-7) belongs to a group of ortho-substituted bromobenzenes that have varying hepatotoxicity effects in the presence of rat liver microsomes in vitro. 2-Bromobenzonitrile is also used as a starting material to synthesize novel benzothiophene derivatives that were found to exhibit antibacterial and antifungal activity.Reference of 2-Bromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts