Tag: 100-200

《On the Nature of C(sp3)-C(sp2) Bond Formation in Nickel-Catalyzed Tertiary Radical Cross-Couplings: A Case Study of Ni/Photoredox Catalytic Cross-Coupling of Alkyl Radicals and Aryl Halides》 was written by Yuan, Mingbin; Song, Zhihui; Badir, Shorouk O.; Molander, Gary A.; Gutierrez, Osvaldo. Safety of 4-Bromobenzonitrile And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

The merger of photoredox and nickel catalysis has enabled the construction of quaternary centers. However, the mechanism, role of the ligand, and effect of the spin state for this transformation and related Ni-catalyzed cross-couplings involving tertiary alkyl radicals in combination with bipyridine and diketonate ligands remain unknown. Several mechanisms have been proposed, all invoking a key Ni(III) species prior to undergoing irreversible inner-sphere reductive elimination. In this work, we have used open-shell dispersion-corrected DFT calculations, quasi-classical dynamics calculations, and experiments to study in detail the mechanism of carbon-carbon bond formation in Ni bipyridine- and diketonate-based catalytic systems. These calculations revealed that access to high spin states (e.g., triplet spin state tetrahedral Ni(II) species) is critical for effective radical cross-coupling of tertiary alkyl radicals. Further, these calculations revealed a disparate mechanism for the C-C bond formation. Specifically, contrary to the neutral Ni-bipyridyl system, diketonate ligands lead directly to the corresponding tertiary radical cross-coupling products via an outer-sphere reductive elimination step via triplet spin state from the Ni(III) intermediates. Implications to related Ni-catalyzed radical cross-couplings and the design of new transformations are discussed. After reading the article, we found that the author used 4-Bromobenzonitrile(cas: 623-00-7Safety of 4-Bromobenzonitrile)

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

《Enhancement of Lipid Productivity of Chlorella sp. Using Light-Converting Red Fluorescent Films Based on Aggregation-Induced Emission》 was published in ACS Sustainable Chemistry & Engineering in 2020. These research results belong to Hwang, Tae Gyu; Kim, Ga-Yeong; Han, Jong-In; Kim, Suhyeon; Kim, Jae Pil. Recommanded Product: 623-00-7 The article mentions the following:

The conversion of light wavelength from green (500-600 nm) to red (600-700 nm) in the solar spectrum can significantly enhance the biodiesel productivity of microalgae because microalgal photosynthetic pigments utilize the red light more efficiently. Herein, we applied light-converting fluorescent films to enhance the biomass and lipid productivity of oleaginous Chlorella sp. Although the fluorescent dyes have been reported to exhibit excellent fluorescence quantum yields in the solution state, the solid film state is more preferred to overcome limitations such as low stability and potential leakage issues. However, conventional fluorescent dyes exhibit poor emission in the solid film state due to aggregation-caused quenching (ACQ). Therefore, this study utilized aggregation-induced emission (AIE)-type diketopyrrolopyrrole (DPP) fluorescent dyes to overcome the ACQ problems and to fabricate highly efficient light-converting red fluorescent films. The fabricated light-converting film showed excellent photosynthetic photon flux d. increase in the red wavelength range by AIE. A maximum total fatty acid Me ester increase of Chlorella sp. was 28.8% using a light-converting film containing a deep-red (650-700 nm) emitting dye M2. In conclusion, we confirmed that the use of solar energy with light-converting films could boost microalgal productivity efficiently, even without using light-emitting diodes that require electricity. This study suggests a simple and efficient method of using solar energy with light-converting films for boosting microalgal productivity.4-Bromobenzonitrile(cas: 623-00-7Recommanded Product: 623-00-7) 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: 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

《Fluorination of arylboronic esters enabled by bismuth redox catalysis》 was published in Science (Washington, DC, United States) in 2020. These research results belong to Planas, Oriol; Wang, Feng; Leutzsch, Markus; Cornella, Josep. Synthetic Route of C7H4FN The article mentions the following:

Triarylbismuth complexes undergo oxidative addition to yield difluorobismuth(V) derivatives, which, upon the reductive elimination provide a valuable route for catalytic fluorination of organoboron compounds Bismuth catalysis has traditionally relied on the Lewis acidic properties of the element in a fixed oxidation state. In this paper, we report a series of bismuth complexes that can undergo oxidative addition, reductive elimination, and transmetalation in a manner akin to transition metals. Rational ligand optimization featuring a sulfoximine moiety produced an active catalyst for the fluorination of aryl boronic esters through a bismuth (III)/bismuth (V) redox cycle. Crystallog. characterization of the different bismuth species involved, together with a mechanistic investigation of the carbon-fluorine bond-forming event, identified the crucial features that were combined to implement the full catalytic cycle. In addition to this study using 4-Fluorobenzonitrile, there are many other studies that have used 4-Fluorobenzonitrile(cas: 1194-02-1Synthetic Route of C7H4FN) was used in this study.

4-Fluorobenzonitrile(cas: 1194-02-1) is used in the synthesis of flurenones, pharmaceutical prerequisites, as well as opiod receptor antagonists.Synthetic Route of C7H4FN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Diversity oriented multi-component reaction (DOS-MCR) approach to access natural product analogues: regio- and chemo-selective synthesis of polyheterocyclic scaffolds via one-pot cascade reactions》 was published in Organic & Biomolecular Chemistry in 2020. These research results belong to Palanivel, Lakshmanan; Gnanasambandam, Vasuki. Quality Control of 3-Oxo-3-phenylpropanenitrile The article mentions the following:

Skeletally diverse and complex aza-cyclopenta(cd)diindenes, pyrrolo(3,4-d)pyridine-13-carboxamides, furo-pyrrolo(1,2-a)imidazole-4-carboxamidesand furo(2,3-b)furans were accessed via one-pot three-component cascade Knoevenagel condensation/Michael addition/Paal-Knorr cyclization of glyoxals and various nitriles. This protocol was metal free, had a good substrate scope and afforded products with good to excellent yields and regio- and chemo-selectivity. The heterocyclic skeletons obtained in this study mimicked natural products such as eupolauramine, gracilamine and presilphiperfolanol. In addition to this study using 3-Oxo-3-phenylpropanenitrile, there are many other studies that have used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Quality Control of 3-Oxo-3-phenylpropanenitrile) was used in this study.

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.Quality Control of 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Discovery of 1,2,4-oxadiazole-Containing hydroxamic acid derivatives as histone deacetylase inhibitors potential application in cancer therapy》 were Yang, Zhuang; Shen, Mingsheng; Tang, Minghai; Zhang, Wanhua; Cui, Xue; Zhang, Zihao; Pei, Heying; Li, Yong; Hu, Mengshi; Bai, Peng; Chen, Lijuan. And the article was published in European Journal of Medicinal Chemistry in 2019. Category: nitriles-buliding-blocks The author mentioned the following in the article:

In this study, a series of novel HDAC inhibitors containing 1,2,4-oxadiazole as the cap group, were synthesized and evaluated in vitro. Compound I, displayed the most potent histone deacetylase (HDAC) inhibition, especially against HDAC1, 2, and 3 with IC50 values of 1.8, 3.6 and 3.0 nM, resp. In vitro antiproliferative studies confirmed that I was more potent than SAHA, with IC50 values against 12 types of cancer cell lines ranging from 9.8 to 44.9 nM. The results of Western blot assays showed that compound I can significantly up-regulate the acetylation of the biomarker his-H3 and mol. docking analyses revealed the mode of action of compound I against HDAC1. The results of flow-cytometry anal. suggested that the above compound induces cell cycle arrest at the G1 phase and has apoptotic effects and further investigation of the activity on the primary cells of three patients, showed IC50 values of 21.3, 61.1, and 77.4 nM. More importantly, an oral bioavailability of up to 53.52% was observed for compound I. An in vivo pharmacodynamic evaluation demonstrated that compound I can significantly inhibit tumor growth in a Daudi Burkitt’s lymphoma xenograft model, with tumor inhibition rates of 53.8 and 46.1% observed at 20 and 10 mg/kg when administered p.o. and i.v., resp. These results indicate that compound I may be a suitable lead for further evaluation and development as an HDAC inhibitors and potent anticancer agents. The experimental process involved the reaction of 4-Cyanobenzyl bromide(cas: 17201-43-3Category: nitriles-buliding-blocks)

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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《An Eco-friendly Synthesis and Biological Screening of Fused Heterocyclic Compounds Containing a Thiophene Moiety via Gewald Reaction》 were El-Borai, Mohamed A.; Rizk, Hala F.; Ibrahim, Seham A.; Fares, Amira K.. And the article was published in Journal of Heterocyclic Chemistry in 2019. Recommanded Product: 3-Oxo-3-phenylpropanenitrile The author mentioned the following in the article:

5-Amino-3-phenyl-1-(2,4,6-trichlorophenyl)-1H-thieno[3,2-c]pyrazole-6-carbonitrile was designed and synthesized by one-pot multicomponent reaction. Compound 5-amino-3-phenyl-1-(2,4,6-trichlorophenyl)-1H-thieno[3,2-c]pyrazole-6-carbonitrile was reacted with different reagents to obtain new condensed moieties with our thienopyrazole skeleton. The compounds e.g., I were prepared by using environmentally benign techniques as microwave irradiation, ultrasonic irradiation and ball-milling. The new compounds e.g., I were evaluated for their in vitro antibacterial and antifungal potentialities. In the experiment, the researchers used many compounds, for example, 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Recommanded Product: 3-Oxo-3-phenylpropanenitrile)

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.Recommanded Product: 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Synthesis of Indoles through Domino Reactions of 2-Fluorotoluenes and Nitriles》 were Mao, Jianyou; Wang, Zhiting; Xu, Xinyu; Liu, Guoqing; Jiang, Runsheng; Guan, Haixing; Zheng, Zhipeng; Walsh, Patrick J.. And the article was published in Angewandte Chemie, International Edition in 2019. HPLC of Formula: 1194-02-1 The author mentioned the following in the article:

A straightforward, practical, and transition-metal-free assembly of 2-aryl indoles was reported. Simply combining readily available 2-fluorotoluenes, nitriles, LiN(SiMe3)2, and CsF enabled the generation of a diverse array of indoles (38 examples, 48-92 % yield). A range of substituents can be introduced into each position of the indole backbone (C4 to C7, and aryl groups at C2), providing handles for further elaboration.4-Fluorobenzonitrile(cas: 1194-02-1HPLC of Formula: 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.HPLC of Formula: 1194-02-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Convenient method for the preparation of hydroxynaphthoic acids》 were Cason, James. And the article was published in Journal of the American Chemical Society in 1941. Recommanded Product: 72016-73-0 The author mentioned the following in the article:

The procedure of Butler and Royle (C. A. 17, 3182) for the synthesis of 4,2-C10H6(CO2H)OH gave very poor yields; various modifications produced the acid in satisfactory yields by way of the same intermediates. 4,2,5-C10H5(NH2)(CO2H)2(345 g.), 390 g. NaOH, 135 g. Zn and 900 cc. H2O, refluxed for 22 h., give 81-7% of 4,2-C10H6(NH2)SO3Na; distillation with KCN at about 500° gives 10-13% of 4,2-C10H6(NH2)CN, m. 125.5-6° (all m. ps. corrected); K4Fe(CN)6 (used by B. and R.) gives only 1-4%; CuCN could not be used because of foaming; a mixture of KCN with NaCN or K4Fe(CN)6 did not give better yields; hydrolysis with a mixture of 10 cc. AcOH and 2.5 cc. 70% H2SO4 gives 86% of 4,2-C10H6(NH2)CO2H, m. 215-16°; the diazo reaction did not give a good yield of 4,2-C10H6(OH)CO2H (I) but heating 4.5 g. of amine and 45 cc. 10% H2SO4 at 195-200° for 4 h. gives 90.5% of I, m. 225-6° (B. and R. give 182-3°); the Ac derivative (II) m. 211.5-12.5° (44° above reported value). II and PCl5, heated at 100° for 25 min., give 88% of 4-acetoxy-2-naphthoyl chloride (III), m. 96-8° and remelting at 99-9.5°; catalytic reduction in boiling xylene (Rosenmund’s method) gives 50-75% of 4-acetoxy-2-naphthaldehyde, m. 113.2-14.2°; semicarbazone (III), m. 230° (decomposition). Hydrolysis with N H2SO4 for 1 h. gives 63% of 2-hydroxy-2-naphthaldehyde (IV), buff, m. 169.5-70°. No definite product could be obtained on Wolff-Kishner reduction of III. Catalytic reduction (Cu-Cr catalyst) of IV gives 4,2-C10H6(OH)Me, m. 90-1°. The Na salt of 1,6-Cleve’s acid yields 9.5-10% of 5,2-C10H6(NH2)CN, m. 143.5-4°; hydrolysis gives 83.5% of 5,2-C10H6(NH2)-CO2H, m. 291-2°; 10% H2SO4 at 220-5° for 4 h. gives 67% of 5,2-C10H6(OH)CO2H, m. 215-16° (Ac derivative, m. 215-16°). 6-Amino-2-naphthonitrile, pale greenish yellow, iridescent plates, m. 199-9.5° (1.5% yield); with K4Fe-(CN)6 the yield is only 0.2%. 6,2-C10H6(OH)CO2H, m. 243-4°, 53.5% (Ac derivative, m. 223-4°). 5,1-C10H6(NH2)CN, m. 139.5-40°, results in 20% yield and 5,1-C10H6(OH)CO2H is formed in 53-7% yield. In the experiment, the researchers used 5-Amino-1-naphthonitrile(cas: 72016-73-0Recommanded Product: 72016-73-0)

5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime. Hydrogen peroxide (H2O2) and peroxy acids generally add an oxygen atom to the nitrogen of amines. With primary amines, this step is normally followed by further oxidation, leading to nitroso compounds, RNO, or nitro compounds, RNO2. Secondary amines are converted to hydroxylamines, R2NOH, and tertiary amines to amine oxides, R3NO.Recommanded Product: 72016-73-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2015,Angewandte Chemie, International Edition included an article by Handa, Sachin; Slack, Eric D.; Lipshutz, Bruce H.. Product Details of 4350-55-4. The article was titled 《Nanonickel-Catalyzed Suzuki-Miyaura Cross-Couplings in Water》. The information in the text is summarized as follows:

Nickel nanoparticles, formed in situ and used in combination with micellar catalysis, catalyze Suzuki-Miyaura cross-couplings in water under very mild reaction conditions. In the experimental materials used by the author, we found 3-(Pyridin-4-yl)benzonitrile(cas: 4350-55-4Product Details of 4350-55-4)

3-(Pyridin-4-yl)benzonitrile(cas: 4350-55-4) 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. Product Details of 4350-55-4 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

Formula: C11H8N2On September 29, 2010 ,《A Highly Selective Low-Background Fluorescent Imaging Agent for Nitric Oxide》 was published in Journal of the American Chemical Society. The article was written by Yang, Youjun; Seidlits, Stephanie K.; Adams, Michelle M.; Lynch, Vincent M.; Schmidt, Christine E.; Anslyn, Eric V.; Shear, Jason B.. The article contains the following contents:

The authors introduce a novel sensing mechanism for nitric oxide (NO) detection with a particular easily synthesized embodiment (NO550), which displays a rapid and linear response to NO with a red shifted 1500-fold turn-on signal from a dark background. Excellent selectivity was observed against other reactive oxygen/nitrogen species, pH, and various substances that interfere with existing probes. NO550 crosses cell membranes but not nuclear membranes and is suitable for both intra- and extracellular NO quantifications. Good cytocompatibility was found during in vitro studies with two different cell lines. The high specificity, dark background, facile synthesis, and low pH dependence make NO550 a superior probe for NO detection when used as an imaging agent. In the part of experimental materials, we found many familiar compounds, such as 5-Amino-1-naphthonitrile(cas: 72016-73-0Formula: C11H8N2)

5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime. Left-handed and right-handed forms (mirror-image configurations, known as optical isomers or enantiomers) are possible when all the substituents on the central nitrogen atom are different (i.e., the nitrogen is chiral). With amines, there is extremely rapid inversion in which the two configurations are interconverted.Formula: C11H8N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts