Month: October 2022

In 2022,Plakas, Konstantinos; Kalogirou, Andreas S.; Kourtellaris, Andreas; Koutentis, Panayiotis A. published an article in Molbank. The title of the article was 《Reaction of 4,5-Dichloro-1,2,3-dithiazolium Chloride with 2-(Phenylsulfonyl)acetonitrile》.Recommanded Product: 614-16-4 The author mentioned the following in the article:

The reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with nitriles (1 equiv) in the presence of pyridine (2 equiv) gave S-(3-chloro-5-cyanoisothiazol-4-yl)benzenesulfonothioate I in 19% and (Z)-2-(5H-1,2,3-dithiazol-5-ylidene)-2-acetonitriles II [R = CN, CO2Me, CO2Et, etc.] were reported. The compounds were fully characterized and the mechanistic rationale was proposed for the formation of the benzensulfonate. In addition to this study using 3-Oxo-3-phenylpropanenitrile, there are many other studies that have used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Recommanded Product: 614-16-4) 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.Recommanded Product: 614-16-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Zheng, Haoteng; Xiao, Qinjie; Mao, Feiying; Wang, Anming; Li, Mu; Wang, Qiuyan; Zhang, Pengfei; Pei, Xiaolin published an article in RSC Advances. The title of the article was 《Programing a cyanide-free transformation of aldehydes to nitriles and one-pot synthesis of amides through tandem chemo-enzymatic cascades》.Safety of 2-Bromobenzonitrile The author mentioned the following in the article:

In this work, a greener chemo-enzymic cascade to synthesize alky and aryl nitriles RCN (R = Ph, Bn, pentyl, furan-2-yl, etc.) from readily accessible aldehydes RCHO, that were further transformed into corresponding amides RC(O)NH2 via an artificial enzyme cascade was reported. A biphasic reaction system was designed to bridge chem. synthesis and enzymic catalysis through simple phase separation The biphasic system mainly perfectly avoided the inactivation of hydroxylamine on aldoxime dehydratase from Pseudomonas putida (OxdF1) and nitrile hydratase from Aurantimonas manganoxydans ATCC BAA-1229 (NHase1229). For the synthesis of various nitriles, moderate isolation yields of approx. 60% were obtained by the chemo-enzymic cascade. Interestingly, two seemingly conflicting reactions of dehydration and hydration were sequentially proceeded to synthesize amides by the synergistic catalysis of OxdF1 and NHase1229 in E. coli cells. An isolation yield of approx. 62% was achieved for benzamide at the one-liter scale. In addition, the shuttle transport of substrates and products between two phases is convenient for the product separation and n-hexane recycling. Thus, the chemo-enzymic cascade shows a potential application in the cyanide-free and large-scale synthesis of nitriles and amides. In the part of experimental materials, we found many familiar compounds, such as 2-Bromobenzonitrile(cas: 2042-37-7Safety 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.Safety of 2-Bromobenzonitrile

Referemce:
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

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Cascade synthesis of novel functionalized pyridine-fused coumarins in aqueous medium》 was published in RSC Advances in 2014. These research results belong to Xiang, Haoyue; Chen, Jianyang; Miao, Zehong; Yang, Chunhao. Quality Control of 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile The article mentions the following:

A simple, convenient and efficient catalyst-free approach for the synthesis of a novel series of pyridine-fused coumarins, e.g., I, via a cascade reaction from chromone derivatives and Et amidinoacetate in an environmentally friendly aqueous medium was developed. This cascade reaction involves a chemoselective Michael addition-heterocyclization-intramol. cyclization sequence. The experimental part of the paper was very detailed, including the reaction process of 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile(cas: 50743-32-3Quality Control of 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile)

6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile(cas: 50743-32-3) 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. Quality Control of 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile 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

《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

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.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2018,Zhang, Xin; Wu, Ge; Gao, Wenxia; Ding, Jinchang; Huang, Xiaobo; Liu, Miaochang; Wu, Huayue published 《Synergistic Photo-Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides with Molecular Oxygen》.Organic Letters published the findings.COA of Formula: C7H3BrFN The information in the text is summarized as follows:

Photoredox-mediated copper-catalyzed hydroxylation of (hetero)aryl halides (including chlorides, bromides and iodides) with O2 at room temperature has been developed. Preliminary mechanistic studies indicate no arylcopper intermediate and that aryl radicals are involved in this procedure. 18O-labeling experiments confirm the hydroxyl oxygen atom originated from mol. oxygen. In the experiment, the researchers used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3COA of Formula: C7H3BrFN)

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.COA of Formula: 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,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

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

《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