Tag: 100-200

《Cobalt-Catalyzed C(sp2)-CN Bond Activation: Cross-Electrophile Coupling for Biaryl Formation and Mechanistic Insight》 was published in ACS Catalysis in 2020. These research results belong to Dorval, Celine; Tricoire, Maxime; Begouin, Jeanne-Marie; Gandon, Vincent; Gosmini, Corinne. Safety of 4-Fluorobenzonitrile The article mentions the following:

Herein, we report a cross-electrophile coupling of benzonitrile derivatives and aryl halides with a simple cobalt-based catalytic system under mild conditions to form biaryl compounds Even though the cobalt catalyst is able to activate the C(sp2)-CN bond alone, the use of the AlMe3 Lewis acid enhances the reactivity of benzonitriles and improves the cross-selectivity with barely any influence on the functional group compatibility. X-ray structure determination of an original low-valent cobalt species combined with catalytic and stoichiometric reactions reveals a catalytically active cobalt(I) species toward the aryl halide partner. On the other hand, exptl. insights, including cyclic voltammetry experiments, suggest the involvement of a cobalt complex of a lower oxidation state to activate the benzonitrile derivative Finally, d. functional theory calculations support the proposed mechanistic cycle involving two low-valent cobalt species of different oxidation states to perform the reaction. The experimental part of the paper was very detailed, including the reaction process of 4-Fluorobenzonitrile(cas: 1194-02-1Safety of 4-Fluorobenzonitrile)

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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Organic aluminum hydrides catalyze nitrile hydroboration》 were Liu, Wenqing; Ding, Yi; Jin, Da; Shen, Qiumiao; Yan, Ben; Ma, Xiaoli; Yang, Zhi. And the article was published in Green Chemistry in 2019. Product Details of 1194-02-1 The author mentioned the following in the article:

Economical and eco-friendly aluminum hydrides were shown to be highly efficient catalysts for the solvent-free hydroboration of various nitriles using pinacolborane. The catalytic activities of three organic aluminum hydrides were compared. Mechanism investigation experiments revealed that nitrile was reduced to an imine intermediate by aluminum hydrides. The experimental process involved the reaction of 4-Fluorobenzonitrile(cas: 1194-02-1Product Details of 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.Product Details of 1194-02-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Chemical Science included an article by Ueda, Yohei; Tsujimoto, Nagataka; Yurino, Taiga; Tsurugi, Hayato; Mashima, Kazushi. Synthetic Route of C7H4FN. The article was titled 《Nickel-catalyzed cyanation of aryl halides and triflates using acetonitrile via C-CN bond cleavage assisted by 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine》. The information in the text is summarized as follows:

A non-toxic cyanation reaction of various aryl halides and triflates in acetonitrile using a catalyst system of [Ni(MeCN)6](BF4)2, 1,10-phenanthroline, and 1,4-bis(trimethylsilyl)-2,3,5,6-tetramethyl-1,4-dihydropyrazine (Si-Me4-DHP) is developed. Si-Me4-DHP was found to function as a reductant for generating nickel(0) species and a silylation reagent to achieve the catalytic cyanation via C-CN bond cleavage. In the part of experimental materials, we found many familiar compounds, such as 4-Fluorobenzonitrile(cas: 1194-02-1Synthetic Route of C7H4FN)

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

Schubert, Thomas; Kula, Maria-Regina; Muller, Michael published their research in Synthesis on December 31 ,1999. The article was titled 《Chemoenzymic synthesis of (S)-8-O-methylmellein by Candida parapsilosis carbonyl reductase》.Safety of 2-Methoxy-6-methylbenzonitrile The article contains the following contents:

Screening of various ortho-substituted (2-oxopropyl)benzene derivatives with carbonyl reductases and alc. dehydrogenases, resp., revealed that compounds containing ortho-substituents with only little steric demand are feasible substrates. (S)-8-O-methylmellein was synthesized by stereoselective enzymic reduction of 2-methoxy-6-(2-oxopropyl)benzonitrile with Candida parapsilosis carbonyl reductase as the key step, and completed by a 1-step hydrolysis and intramol. cyclization. After reading the article, we found that the author used 2-Methoxy-6-methylbenzonitrile(cas: 53005-44-0Safety of 2-Methoxy-6-methylbenzonitrile)

2-Methoxy-6-methylbenzonitrile(cas: 53005-44-0) 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. Safety of 2-Methoxy-6-methylbenzonitrile 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.

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Synthesis and evaluation of thymol-based synthetic derivatives as dual-action inhibitors against different strains of H. pylori and AGS cell line》 was written by Sisto, Francesca; Carradori, Simone; Guglielmi, Paolo; Spano, Mattia; Secci, Daniela; Granese, Arianna; Sobolev, Anatoly P.; Grande, Rossella; Campestre, Cristina; Marcantonio, Maria Carmela Di; Mincione, Gabriella. Electric Literature of C8H6BrNThis research focused onthymol ether preparation helicobacter pylori antibacterial gastric adenocarcinoma; AGS cells; Helicobacter pylori; drug resistance; dual-action agents, antimicrobial activity; semi-synthesis; thymol. The article conveys some information:

Herein, the synthesis of a new series of thymol-based ethers I [R = Me, H2C:CH, CN, EtO2C, Ph, 2-BrC6H4, etc.] and their microbiol. screening against eight strains of H. pylori and the cytotoxic activity against human gastric adenocarcinoma (AGS) cells are reported. Structural anal. comprehended elemental anal. and 1H/13C/19F NMR spectra. The anal. of structure-activity relationships within this mol. library of these structurally-related compounds showed that some chem. modifications of the OH group of thymol led to broad-spectrum growth inhibition on all isolates. Preferred substitutions were benzyl groups compared to alkyl chains and the specific presence of functional groups at para position of the benzyl moiety such as 4-CN and 4-Ph endowed the most anti-H. pylori activity toward all the strains with min. inhibitory concentration (MIC) values up to 4μg/mL. Poly-substitution on the benzyl ring was not essential. Moreover, several compounds characterized by the lowest min. inhibitory concentration/min. bactericidal concentration (MIC/MBC) values against H. pylori were also tested in order to verify a cytotoxic effect against AGS cells with respect to 5-fluorouracil and carvacrol. In the experiment, the researchers used many compounds, for example, 4-Cyanobenzyl bromide(cas: 17201-43-3Electric Literature of C8H6BrN)

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.Electric Literature of C8H6BrN

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Computed Properties of C9H7NOIn 2020 ,《Transition metal-free cyclization of N-Boc-N-propargylenamines》 appeared in Heterocycles. The author of the article were Chikayuki, Yuya; Kouno, Yasuaki; Yonekawa, Shiori; Ishikawa, Haruka; Waki, Yoko; Teramoto, Hiroyoshi; Sasaki, Shigeru; Higashiyama, Kimio; Yamauchi, Takayasu. The article conveys some information:

An efficient method for the synthesis of multi-substituted pyrroles was developed using basic cyclization of readily accessible N-Boc-N-propargylenamines. Despite the basic conditions, cleavage of the N-Boc group occurred easily. The process was rapid and afforded N-H-pyrroles with wide functional group tolerance in high yields. After reading the article, we found that the author used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Computed Properties of C9H7NO)

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used in the synthesis of substituted naphtho[1,8-bc]pyrans. It was also used as building block in the preparation of 4H-pyrans, 2-pyridones, furans and carbocyclics.Computed Properties of C9H7NO

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Recommanded Product: 31938-07-5In 2000 ,《Histamine H1 receptor ligands part II. Synthesis and in vitro pharmacology of 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives》 was published in Farmaco. The article was written by Walczynski, Krzysztof; Guryn, Roman; Zuiderveld, Obbe P.; Zhang, Ming-Qiang; Timmerman, Henk. The article contains the following contents:

New 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives were prepared and tested in vitro as H1 receptor antagonists. The compounds with 2-phenylamino substitution with meta-halide substituents at the Ph ring, showed weak H1-antagonistic activity (pA2: 4.62-5.04) and this activity was completely lost in the case of meta-Me substituents (pA2 < 4). When the phenylamino group was replaced by benzhydryl groups of classic antihistamines, the resulting compounds exhibited slightly improved H1-antagonistic activity (at the meta-position pA2: 6.38-6.15; at the para-position pA2: 6.04-5.87).2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Recommanded Product: 31938-07-5) was used in this study.

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

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

HPLC of Formula: 1194-02-1In 2021 ,《Sensitization-initiated electron transfer via upconversion: mechanism and photocatalytic applications》 was published in Chemical Science. The article was written by Glaser, Felix; Kerzig, Christoph; Wenger, Oliver S.. The article contains the following contents:

Sensitization-initiated electron transfer (SenI-ET) describes a recently discovered photoredox strategy that relies on two consecutive light absorption events, triggering a sequence of energy and electron transfer steps. The cumulative energy input from two visible photons gives access to thermodynamically demanding reactions, which would be unattainable by single excitation with visible light. For this reason, SenI-ET has become a very useful strategy in synthetic photochem., but the mechanism has been difficult to clarify due to its complexity. We demonstrate that SenI-ET can operate via sensitized triplet-triplet annihilation upconversion, and we provide the first direct spectroscopic evidence for the catalytically active species. In our system comprised of fac-[Ir(ppy)3] as a light absorber, 2,7-di-tert-butylpyrene as an annihilator, and N,N-dimethylaniline as a sacrificial reductant, all photochem. reaction steps proceed with remarkable rates and efficiencies, and this system is furthermore suitable for photocatalytic aryl dehalogenations, pinacol couplings and detosylation reactions. The insights presented here are relevant for the further rational development of photoredox processes based on multi-photon excitation, and they could have important implications in the greater contexts of synthetic photochem. and solar energy conversion. In addition to this study using 4-Fluorobenzonitrile, there are many other studies that have used 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

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

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