Month: October 2022

《A Photophysical Study of Sensitization-Initiated Electron Transfer: Insights into the Mechanism of Photoredox Activity》 was written by Coles, Max S.; Quach, Gina; Beves, Jonathon E.; Moore, Evan G.. Application of 2042-37-7 And the article was included in Angewandte Chemie, International Edition in 2020. The article conveys some information:

The development of photocatalytic reactions has provided many novel opportunities to expand the scope of synthetic organic chem. In parallel with progress towards uncovering new reactivity, there is consensus that efforts focused on providing detailed mechanistic insight in order to uncover underlying excited-state reactions are essential to maximise formation of desired products. With this in mind, we have investigated the recently reported sensitization-initiated electron transfer (SenI-ET) reaction for the C-H arylation of activated aryl halides. Using a variety of techniques, and in particular nanosecond transient absorption spectroscopy, we are able to distinguish several characteristic signals from the excited-state species involved in the reaction, and subsequent kinetic anal. under various conditions has facilitated a detailed insight into the likely reaction mechanism. After reading the article, we found that the author used 2-Bromobenzonitrile(cas: 2042-37-7Application 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.Application of 2042-37-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zafari, Parvin; Saatluo, Bahman Ebrahimi; Rashidi, Ahmad; Baradarani, Mehdi M.; Joule, John A. published their research in ARKIVOC (Gainesville, FL, United States) in 2021. The article was titled 《Three-component synthesis of novel spiro[4H-pyran-3,3′-oxindoles] using 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione》.SDS of cas: 614-16-4 The article contains the following contents:

One-pot, three-component reactions of the tricyclic isatin 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione with variously substituted aryl cyanomethyl ketones and malononitrile, or Et cyanoacetate, generated spiro[4H-pyran-3,3′-oxindoles] I [X = CN, COOEt; R = H, 4-Me, 4-Cl, etc.] such as, 2-amino-2′-oxo-6-(phenyl)-5′,6′-dihydro-2’H,4’H-spiro[pyran-4,1′-pyrrolo[3,2,1-ij]quinoline]-3,5-dicarbonitrile. The experimental part of the paper was very detailed, including the reaction process of 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4SDS of cas: 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.SDS of cas: 614-16-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Chen, Xiaolu; Liu, Yanan; Zhang, Liting; Chen, Daoxing; Dong, Zhaojun; Zhao, Chengguang; Liu, Zhiguo; Xia, Qinqin; Wu, Jianzhang; Chen, Yongheng; Zheng, Xiaohui; Cai, Yuepiao published an article in 2021. The article was titled 《Design, synthesis, and biological evaluation of indazole derivatives as selective and potent FGFR4 inhibitors for the treatment of FGF19-driven hepatocellular cancer》, and you may find the article in European Journal of Medicinal Chemistry.Synthetic Route of C7H3BrFN The information in the text is summarized as follows:

Fibroblast growth factor receptor 4 (FGFR4) is a member of the fibroblast growth factor receptor family, which is closely related to the occurrence and development of hepatocellular carcinoma (HCC). In this article, a series of indazole derivatives were designed and synthesized by using computer-aided drug design (CADD) and structure-based design strategies, and then they were evaluated for their inhibition of FGFR4 kinase and antitumor activity. F-30 was subtly selective for FGFR4 compared to FGFR1; it affected cell growth and migration by inhibiting FGFR4 pathways in HCC cell lines in a dose-dependent manner. In the experimental materials used by the author, we found 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Synthetic Route of 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.Synthetic Route 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 2022,Planas, Oriol; Peciukenas, Vytautas; Leutzsch, Markus; Noethling, Nils; Pantazis, Dimitrios A.; Cornella, Josep published an article in Journal of the American Chemical Society. The title of the article was 《Mechanism of the Aryl-F Bond-Forming Step from Bi(V) Fluorides》.Safety of 4-Fluorobenzonitrile The author mentioned the following in the article:

The authors describe a combined exptl. and theor. mechanistic study of the C(sp2)-F bond formation from neutral and cationic high-valent organobismuth(V) fluorides, featuring a dianionic bis-aryl sulfoximine ligand. An exhaustive assessment of the substitution pattern in the ligand, the sulfoximine, and the reactive aryl on neutral triarylbismuth(V) difluorides revealed that formation of dimeric structures in solution promotes facile Ar-F bond formation. Noteworthy, theor. modeling of reductive elimination from neutral Bi(V) difluorides agrees with the exptl. determined kinetic and thermodn. parameters. Also, the addition of external fluoride sources leads to inactive octahedral anionic Bi(V) trifluoride salts, which decelerate reductive elimination. However, a parallel anal. for cationic bismuthonium fluorides revealed the crucial role of tetrafluoroborate anion as fluoride source. Both exptl. and theor. analyses conclude that C-F bond formation occurs through a low-energy five-membered transition-state pathway, where the F anion is delivered to a C(sp2) center, from a BF4 anion, reminiscent of the Balz-Schiemann reaction. The knowledge gathered throughout the study permitted a rational assessment of the key parameters of several ligands, identifying the simple sulfone-based ligand family as an improved system for the stoichiometric and catalytic fluorination of arylboronic acid derivatives In the experiment, the researchers used 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

Related Products of 623-00-7In 2020 ,《Supercritical carbon dioxide extraction of a biaryl from model product solutions of a flow Suzuki-Miyaura coupling reaction》 was published in Journal of Chemical Engineering of Japan. The article was written by Fujii, Tatsuya; Kawasaki, Shin-ichiro. The article contains the following contents:

The present study investigates the extraction of a target chem., 4-cyanobiphenyl, from model product solutions of a flow Suzuki-Miyaura coupling reaction. Fast flow extraction from an ethanol aqueous solution of 4-cyanobiphenyl was conducted using supercritical carbon dioxide as the extraction solvent under conditions of 40-60°C and 10-20 MPa. More than 80% of the 4-cyanobiphenyl was recovered in the CO2-rich phase, and the rate was greater than 5.0 g-4-cyanobiphenyl/h for the extraction at 60°C and 20 MPa from the model solution containing salts. The effects of the ethanol mole fraction and the extraction pressure were also investigated to elucidate the effect of changes in the solvent properties on the partitioning behavior. The 4-cyanobiphenyl partition coefficient decreased with increasing ethanol mole fraction and increased with increasing extraction pressure. A model that includes the effects of changes in solubility with increasing CO2 d. and ethanol mole fraction in the water- and CO2-rich phases was developed. The model well represents the tendency of the partitioning behavior, which indicates that the CO2 d. and ethanol mole fraction in each phase are important factors governing the partitioning behavior. In addition to this study using 4-Bromobenzonitrile, there are many other studies that have used 4-Bromobenzonitrile(cas: 623-00-7Related Products of 623-00-7) was used in this study.

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

Category: nitriles-buliding-blocksIn 2018 ,《Design, synthesis and biological evaluation of a series of novel GPR40 agonists containing nitrogen heterocyclic rings》 was published in Bioorganic & Medicinal Chemistry Letters. The article was written by Sun, Zhaozhu; Zhou, Tian; Pan, Xuan; Yang, Ying; Huan, Yi; Xiao, Zhiyan; Shen, Zhufang; Liu, Zhanzhu. The article contains the following contents:

A novel series of GPR40 agonists is designed by introducing nitrogen-containing heterocyclic ring at the terminal Ph ring of TAK-875 (I) with the aim of decreasing its lipophilicity. Three different β-substituted phenylpropionic acids were investigated as the acidic components. A total of 34 compounds have been synthesized, among which, compound II exhibited comparable GPR40 agonistic activity in vitro with TAK-875 and relatively lower lipophilicity through calculation (II: EC50 = 1.2 μM, cLogP = 1.3; TAK-875: EC50 = 5.1 μM, cLogP = 3.4). Moreover, compound II was able to enhance the insulin secretion of primary islets isolated from normal ICR mice and showed no obvious inhibition against cytochromes P 450 in vitro. In vivo, compound II exhibited efficacy in oral glucose tolerance test (oGTT) in normal ICR mice. The experimental part of the paper was very detailed, including the reaction process of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Category: nitriles-buliding-blocks)

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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《13C NMR investigated of electronic interactions in 5-substituted 1-naphthonitriles》 was written by Schuster, Ingeborg I.. Product Details of 72016-73-0 And the article was included in Magnetic Resonance in Chemistry on April 30 ,1996. The article conveys some information:

Carbon-13 NMR chem. shifts of 5-Z-substituted 1-naphthonitriles (1; Z = H, F, Cl, Br, NH2, NMe2, CN, NO2, OMe, CHO, CO2Me) in deuteriochloroform and in neat trifluoroacetic acid (TFA) are reported. The CN carbon shifts are found to correlate well with the dual substituent parameters (DSPs). Neg. values of the transmission coefficients in the DSP correlation give evidence of a reverse substituent electronic effect, which is associated with variations in π polarization of the CN multiple bond, due primarily to differences in the through-space field effects of the various Z. The effect diminishes for 1 in neat TFA because of the greater contribution of dipolar ArC+=N- to the resonance hybrid. Deviations of the aromatic carbon shifts from substituent chem. shift additives are small, yet show distinct patterns for many of the carbon resonances. The deviations of the C-1-CN ipso carbon shifts of 1 in neutral solvents and in TFA correlate roughly with the DSPs. They are attributable to changes in charge d. at C-1 that arise as a consequence of substituent- and increased mesomeric activity by electron-donating groups, Z, in response to the CN-induced charge depletion within the adjacent aromatic ring. From the location of data for 5-methoxy-1-naphthonitrile (1; Z = OMe) in the chem. shift correlations of 1 in neat TFA, one can conclude that the methoxy group of this compound, unlike that of 1-methoxynaphthalene itself, is not significantly hydrogen-bonded by TFA. The experimental part of the paper was very detailed, including the reaction process of 5-Amino-1-naphthonitrile(cas: 72016-73-0Product Details of 72016-73-0)

5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime. Examples of direct uses of amines and their salts are as corrosion inhibitors in boilers and in lubricating oils (morpholine), as antioxidants for rubber and roofing asphalt (diarylamines), as stabilizers for cellulose nitrate explosives (diphenylamine), as protectants against damage from gamma radiation (diarylamines), as developers in photography (aromatic diamines), as flotation agents in mining, as anticling and waterproofing agents for textiles, as fabric softeners, in paper coating, and for solubilizing herbicides.Product Details of 72016-73-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of C43H30F2N4On October 11, 2021 ,《Metal-to-Ligand Ratio-Dependent Chemodivergent Asymmetric Synthesis》 was published in Angewandte Chemie, International Edition. The article was written by Zheng, Min; Gao, Ke; Qin, Haitao; Li, Guigen; Lu, Hongjian. The article contains the following contents:

Chemodivergent asym. synthesis was achieved by tuning the metal-to-ligand ratio in an organometallic catalytic system. Using N-(aroyloxy)phthalimides I (Ar = 2,6-difluorophenyl, 2,3,4,5,6-pentafluorophenyl, Ph, etc.; R = 4-bromophenyl, thiophen-2-yl, Bu, etc.) as the precursor of either an oxygen-centered aroyloxy radical or a nitrogen-centered phthalimidyl radical, enantioselective oxocyanation or aminocyanation of alkenes RCH=CH2 was achieved sep. through a dual photoredox and copper catalysis. The metal-to-ligand ratio can exert chemoselective control while retaining the high enantiopurity of divergent products II, (2R)-RCH(CN)CH2OC(O)Ar. Both reactions proceed efficiently with catalyst loading as low as 0.2 mol% and can be performed on a gram scale without loss of chemoselectivity or enantioselectivity. Chemodivergent asym. 1,5-aminocyanation or 1,5-oxocyanation of vinylcyclopropane can also be realized by this protocol. Mechanistic investigations involving ESR (EPR) experiments were performed to shed light on the stereochem. and chemodivergent results. The results came from multiple reactions, including the reaction of 2,4,6-Tris(diphenylamino)-3,5-difluorobenzonitrile(cas: 1403850-00-9Synthetic Route of C43H30F2N4)

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.Synthetic Route of C43H30F2N4

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

In 2013,European Journal of Organic Chemistry included an article by Gogoi, Pranjal; Bezboruah, Pranjal; Boruah, Romesh C.. Name: 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile. The article was titled 《Ligand-free Suzuki cross-coupling reactions: application to β-halo-α,β-unsaturated aldehydes》. The information in the text is summarized as follows:

A facile, efficient, ligand-free Suzuki-Miyaura reaction of β-halo α,β-unsaturated aldehydes with boronic acids in aqueous media at room temperature is described. Under the optimized conditions, both steroidal and nonsteroidal β-halo α,β-unsaturated aldehydes reacted rapidly with the boronic acids to provide a series of aryl-substituted derivatives in excellent yields. Moreover, the protocol was extended to the direct one-pot synthesis of polycyclic aromatic hydrocarbons through a Suzuki-Miyaura cross-coupling/aldol condensation cascade reaction under microwave irradiation In the experimental materials used by the author, we found 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile(cas: 325141-71-7Name: 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile)

2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile(cas: 325141-71-7) 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. Name: 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile 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