Tag: 100-200

《Efficient Co-Catalyzed Double Hydroboration of Nitriles: Application to One-Pot Conversion of Nitriles to Aldimines》 was written by Gudun, Kristina A.; Slamova, Ainur; Hayrapetyan, Davit; Khalimon, Andrey Y.. Product Details of 1194-02-1 And the article was included in Chemistry – A European Journal in 2020. The article conveys some information:

The com. available and bench-stable Co(acac)2/dpephos system was employed as a precatalyst for selective and efficient room temperature hydroboration of organic nitriles with HBPin to produce a series of N,N-diborylamines [RN(BPin)2], which reacted in-situ with aldehydes to give aldimines. Formation of aldimines from N,N-diborylamines does not require a dehydrating agent, is applicable to a wide range of N,N-diborylamine and aldehyde substrates and is highly chemoselective, being unaffected by various common functional groups, such as alkenes, alkynes, secondary amines, ketones, esters, amides, carboxylic acids, pyridines, nitriles, and nitro compounds The overall transformation represents a synthetically valuable approach to aldimines from nitriles and can be performed in a sequential one-pot manner, tolerating ester, lactone, carboxamide and unactivated alkene functionalities. In the part of experimental materials, we found many familiar compounds, such as 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

The author of 《A Transition-Metal-Free One-Pot Cascade Process for Transformation of Primary Alcohols (RCH2OH) to Nitriles (RCN) Mediated by SO2F2》 were Jiang, Ying; Sun, Bing; Fang, Wan-Yin; Qin, Hua-Li. And the article was published in European Journal of Organic Chemistry in 2019. SDS of cas: 1194-02-1 The author mentioned the following in the article:

Primary (benzylic) alcs. underwent transition-metal-free one-pot cascade process with SO2F2, K2CO3, and NH2OH·HCl in DMSO to yield nitriles without introducing an addnl. carbon atom. In the part of experimental materials, we found many familiar compounds, such as 4-Fluorobenzonitrile(cas: 1194-02-1SDS of cas: 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.SDS of cas: 1194-02-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《A Novel Iron-catalyzed One-pot Synthesis of 3-Amino-1,2,4-triazoles》 were Rohand, Taoufik; Mkpenie, Victor N.; El Haddad, Mohammadine; Marko, Istvan E.. And the article was published in Journal of Heterocyclic Chemistry in 2019. Product Details of 2042-37-7 The author mentioned the following in the article:

A novel one-pot synthesis of 3-amino-1,2,4-triazole developed via iron(III) catalyzed route is reported [e.g., benzonitrile + cyanamide + hydroxylamine hydrochloride → I (81%) in presence of FeCl3, PMe3 and base]. The new method is more efficient, simple, and convenient and presents a concise new strategy for the synthesis of 3-amino-1,2,4-triazole derivatives The iron(III) complex intermediate assisted in the intramol. bond cyclization owing to its Lewis acidity or oxidizing properties. A series of aromatic nitriles bearing different electron-donating and electron-withdrawing groups substituted at para and/or ortho positions were also investigated. The position of the substituents affected the yield of the final compound, with the para-substituted substrates giving relatively higher yields. After reading the article, we found that the author used 2-Bromobenzonitrile(cas: 2042-37-7Product Details of 2042-37-7)

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.Product Details of 2042-37-7

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Nitrile – Wikipedia,
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In 2019,Angewandte Chemie, International Edition included an article by Liu, Dong; Ma, Hong-Xing; Fang, Ping; Mei, Tian-Sheng. Reference of 4-Bromobenzonitrile. The article was titled 《Nickel-Catalyzed Thiolation of Aryl Halides and Heteroaryl Halides through Electrochemistry》. The information in the text is summarized as follows:

The Nickel-catalyzed electrochem. thiolation of aryl bromides and chlorides in the absence of an external base at room temperature using undivided electrochem. cells was reported for the synthesis of diaryl sulfides e.g., I. The experimental part of the paper was very detailed, including the reaction process of 4-Bromobenzonitrile(cas: 623-00-7Reference 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,Reference 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.

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Organic & Biomolecular Chemistry included an article by West, Matthew J.; Watson, Allan J. B.. Name: 2-Bromobenzonitrile. The article was titled 《Ni vs. Pd in Suzuki-Miyaura sp2-sp2 cross-coupling: a head-to-head study in a comparable precatalyst/ligand system》. The information in the text is summarized as follows:

Despite significant advances, ligand development for Ni-catalyzed Suzuki-Miyaura cross-coupling remains underdeveloped when compared to Pd and, as a consequence, ligands for Ni-catalyzed processes are typically taken from the Pd arena. In this study, the effect of using a similar Ni and Pd precatalyst based on a common bidentate ligand (dppf) in a head-to-head format was evaluated for the most common type of biaryl couplings, establishing the practical implications of direct replacement of Pd with Ni, and identifying the potential origins of these observations in a mechanistic context. After reading the article, we found that the author used 2-Bromobenzonitrile(cas: 2042-37-7Name: 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. In addition, 2-bromobenzonitrile can be used for the Suzuki coupling reaction.Name: 2-Bromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2010,Feng, Xiao-Qing; Zeng, Zhao-Sen; Liang, Yong-Hong; Chen, Fen-Er; Pannecouque, Christophe; Balzarini, Jan; De Clercq, Erik published 《Synthesis and biological evaluation of 4-(hydroxyimino)arylmethyl diarylpyrimidine analogues as potential non-nucleoside reverse transcriptase inhibitors against HIV》.Bioorganic & Medicinal Chemistry published the findings.Related Products of 31938-07-5 The information in the text is summarized as follows:

A series of novel diarylpyrimidine analogs featuring a hydroxyiminomethyl group between the pyrimidine scaffold and the aryl wing I have been synthesized and tested in MT-4 cells culture as non-nucleoside reverse transcriptase inhibitors against human immunodeficiency virus (HIV). Most of these new congeners exhibited moderate to excellent activity against wild-type virus with an EC50 value ranging from 0.569 μM to 0.005 μM. 4-(4-((Hydroxyimino) (3-methoxyphenyl)methyl)pyrimidin-2-ylamino)benzonitrile (12n) was identified as the most active compound of this new series (EC50 = 0.025 μM, SI >1223) associated with moderate activity against HIV-1 double mutant strains (K103N + Y181C) (EC50 = 8.72 μM) in addition to its anti-HIV-2 activity with an EC50 value of 8.31 μM. Preliminary structure-activity relationship (SAR) among the newly synthesized DAPYs was also investigated. In addition to this study using 2-(3-Bromophenyl)acetonitrile, there are many other studies that have used 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Related Products of 31938-07-5) was used in this study.

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

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Nitrile – Wikipedia,
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《Triflic Acid as an Efficient Bronsted Acid Promoter for the Umpolung of N-Ac Indoles in Hydroarylation Reactions》 was published in Advanced Synthesis & Catalysis in 2018. These research results belong to Nandi, Raj Kumar; Perez-Luna, Alejandro; Gori, Didier; Beaud, Rodolphe; Guillot, Regis; Kouklovsky, Cyrille; Gandon, Vincent; Vincent, Guillaume. Safety of 3-Formyl-1H-indole-6-carbonitrile The article mentions the following:

We report that triflic acid, a strong Bronsted acid, is a very powerful alternative to FeCl3 to mediate the hydroarylation of N-Ac indoles, which delivers regioselectively 3-arylindolines, 3,3-spiroindolines or 2-arylindolines. Mechanistic explorations point towards the existence of a highly electrophilic intermediate by simultaneous activation of the acetyl and of the C2=C3 bond by protons. After reading the article, we found that the author used 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Safety of 3-Formyl-1H-indole-6-carbonitrile)

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.Safety of 3-Formyl-1H-indole-6-carbonitrile

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Nitrile – Wikipedia,
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COA of Formula: C7H4FNIn 2019 ,《Selective synthesis of secondary amines from nitriles by a user-friendly cobalt catalyst》 was published in Advanced Synthesis & Catalysis. The article was written by Sharma, Dipesh M.; Punji, Benudhar. The article contains the following contents:

A simple, inexpensive and user-friendly cobalt-catalyzed method for the selective and practical synthesis of sym. and unsym. secondary amines RCH2NR1R2 [R = Pr, Ph, Bn, etc.; R1 = H, Me, Et; R2 = N-morpholinyl, Ph, 4-pyridyl, etc.] was developed via reductive amination of nitriles. The use of (xantphos)CoCl2 and ammonia borane (NH3-BH3) combination afforded the selective reduction of nitriles to sym. secondary amines, whereas the employment of (xantphos)CoCl2 and dimethylamine borane along with external amines produced unsym. secondary amines and tertiary amines. The reaction tolerated diverse functionalities, such as alkyl, alkyl ether, halides and heteroarenes. The results came from multiple reactions, including the reaction of 4-Fluorobenzonitrile(cas: 1194-02-1COA of Formula: C7H4FN)

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.COA of Formula: C7H4FN

Referemce:
Nitrile – Wikipedia,
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Synthetic Route of C9H7NOIn 2022 ,《Lewis Acid-Relayed Singlet Oxygen Reaction with Enamines: Selective Dimerization of Enamines to Pyrrolin-4-ones》 appeared in Journal of the American Chemical Society. The author of the article were Lei, Tao; Cheng, Yuan-Yuan; Han, Xu; Zhou, Chao; Yang, Bing; Fan, Xiu-Wei; Chen, Bin; Tung, Chen-Ho; Wu, Li-Zhu. The article conveys some information:

Singlet oxygen (1O2)-mediated oxidation represents an attractive strategy for incorporation of oxygen atoms from air under mild and environmentally benign conditions. However, the 1O2 reaction with enamine suffers from fragmentation, leading to very unsuccessful transformation. Here, Lewis acid is introduced to intercept [2 + 2] or “”ene”” reaction intermediates of the 1O2 reaction and enables oxidative dimerization of enamines to produce pyrrolin-4-ones in good to excellent yields. Mechanistic studies reveal the formation of the imino ketone intermediate from the interaction of 1O2 and enamine, which is able to interact with Lewis acid, relaying the 1O2 reaction in enamine chem. For the first time, selective cross-dimerization of two different enamines is achieved. Due to the advantages of mild conditions, high chemoselectivity, and up to 99% yield, a promising strategy has been developed for synthesizing aza-heterocycles under ambient conditions, which can be further applied for the synthesis of imidazolone, quinoxaline, and highly functionalized imine. In the experiment, the researchers used many compounds, for example, 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Synthetic Route 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.Synthetic Route of C9H7NO

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Wen, Xiaoting; He, Jingxi; Xi, Hui; Zheng, Qi; Liu, Weiping published an article in 2022. The article was titled 《Hydration of Nitriles Enabled by PNP-manganese Pincer Catalyst》, and you may find the article in Asian Journal of Organic Chemistry.Quality Control of 2-Bromobenzonitrile The information in the text is summarized as follows:

A general and practical methodol. for the hydration of nitriles to primary amides enabled by manganese catalyst was presented. The described protocol showed broad substrate scope with good functional group tolerance, including a wide range of (hetero)aromatic and aliphatic nitriles, thus afforded the corresponding amides RC(O)NH2 [R = c-hexyl, Ph, 2-furyl., etc.] in good to excellent isolated yields under mild conditions. Preliminary mechanistic studies indicated that metal-ligand cooperation (MLC) mode was involved in this catalytic process. In the experiment, the researchers used many compounds, for example, 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. In addition, 2-bromobenzonitrile can be used for the Suzuki coupling reaction.Quality Control of 2-Bromobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts