Month: October 2022

《Electrochemical C-H Cyanation of Electron-Rich (Hetero)Arenes》 was published in Chemistry – A European Journal in 2018. These research results belong to Hayrapetyan, Davit; Rit, Raja K.; Kratz, Markus; Tschulik, Kristina; Goossen, Lukas J.. Recommanded Product: 53005-44-0 The article mentions the following:

A straightforward method for the electrochem. C-H cyanation of arenes and heteroarenes that proceeds at room temperature in MeOH, with NaCN as the reagent in a simple, open, undivided electrochem. cell to afford aryl nitriles was reported. The platinum electrodes were passivated by adsorbed cyanide, which allowed conversion of an exceptionally broad range of electron-rich substrates all the way down to dialkyl arenes. The cyanide electrolyte could be replenished with HCN, opening opportunities for salt-free industrial C-H cyanation. In the part of experimental materials, we found many familiar compounds, such as 2-Methoxy-6-methylbenzonitrile(cas: 53005-44-0Recommanded Product: 53005-44-0)

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. Organic compounds containing multiple nitrile groups are known as cyanocarbons.Recommanded Product: 53005-44-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrileOn March 4, 2016, Tsukamoto, Hirokazu; Ikeda, Taishi; Doi, Takayuki published an article in Journal of Organic Chemistry. The article was 《Palladium(II)-Catalyzed Annulation of Alkynes with 2-(Cyanomethyl)phenylboronates Leading to 3,4-Disubstituted 2-Naphthalenamines》. The article mentions the following:

1,2-Bis(diphenylphosphino)ethane (dppe)-ligated palladium(II) complexes catalyze the annulation of internal alkynes with 2-(cyanomethyl)phenylboronates to provide 3,4-disubstituted-2-naphthalenamines in good yields. The annulation reaction proceeds under mild and neutral conditions and requires methanol as an essential solvent. In addition to sym. alkynes, unsym. alkynes substituted by aryl, alkyl, and alkynyl groups participate in the annulation to afford the corresponding 2-naphthalenamines with electron-withdrawing sp2- and sp-carbons preferentially located at the C-3 position. Substituents including an alkyl or alkoxy group on the cyanomethyl moiety and a halogen atom on the benzene ring in the boronates are compatible with the reaction conditions. The annulation proceeds through the transmetalation of the palladium(II) complexes with the boronates and alkyne insertion followed by nucleophilic addition of the generated alkenylpalladium(II) species to the intramol. cyano group. Stoichiometric reactions revealed that the methanol solvent was effective for both transmetalation and catalyst regeneration. In the experiment, the researchers used 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile(cas: 325141-71-7Reference of 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. Organic compounds containing multiple nitrile groups are known as cyanocarbons.Reference of 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Recommanded Product: 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrileOn October 25, 1985 ,《Synthesis of the metabolites and degradation products of 2-amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acid (amoxanox)》 was published in Chemical & Pharmaceutical Bulletin. The article was written by Ukawa, Kiyoshi; Ishiguro, Toshihiro; Kuriki, Hisashi; Nohara, Akira. The article contains the following contents:

Benzopyranopyridinecarboxylic acid I (R = CHMe2), a promising drug for bronchial asthma, was converted to various degradation products, I (R = CMe2OH, CHMeCH2OH, COMe), which were also synthesized from benzopyranonitrile. On testing for passive cutaneous anaphylaxis in rats, I (R = CHMe2, CMe2OH, COMe) were 260 times as potent as disodium cromoglycate (DSCG) while I (R = CMeCH2OH) was 1500 times as potent as DSCG. In the experimental materials used by the author, we found 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile(cas: 50743-32-3Recommanded Product: 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. Recommanded Product: 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

SDS of cas: 86776-52-5On September 30, 1984 ,《Synthesis and some properties of 3-fluoro-4-cyanophenyl 4′-n-alkylbenzoates》 was published in Molecular Crystals and Liquid Crystals. The article was written by Sasaki, M.; Takeuchi, K.; Sato, H.; Takatsu, H.. The article contains the following contents:

A series of 3-fluoro-4-cyanophenyl 4′-n-alkylbenzoates, which show monotropic nematic phases, was prepared and their transition temperatures and melting enthalpies were measured. The 3-fluoro-4-cyanophenyl 4′-n-propylbenzoate, 3-chloro-4-cyanophenyl 4′-n-propylbenzoate, and 4-cyanophenyl 4′-n-propylbenzoate were mixed with a nematic mixture (A) of 4-n-alkoxyphenyl 4′-n-alkylcyclohexane-1′-carboxylates. 3-Fluoro-4-cyanophenyl 4′-n-propylbenzoate decreases the N-I transition temperature less, increases the birefringence more, and increases the bulk viscosity less than 3-chloro-4-cyanophenyl 4′-n-propylbenzoate, and reduces the threshold voltage to the greatest extent. The dielec. anisotropies of 3-fluoro-4-cyanophenyl 4′-n-propylbenzoate and 4-cyanophenyl 4′-n-propylbenzoate determined from a series of solutions of the compounds in nematic mixture (A) are 35.9 and 29.6, resp. In the part of experimental materials, we found many familiar compounds, such as 4-Cyano-3-fluorophenyl 4-butylbenzoate(cas: 86776-52-5SDS of cas: 86776-52-5)

4-Cyano-3-fluorophenyl 4-butylbenzoate(cas: 86776-52-5) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).SDS of cas: 86776-52-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Schofield, Joseph; Derdau, Volker; Atzrodt, Jens; Zane, Patricia; Guo, Zuyu; van Horn, Robert; Czepczor, Valerie; Stoltz, Axelle; Pardon, Magalie published an article in Bioorganic & Medicinal Chemistry. The title of the article was 《Effect of deuteration on metabolism and clearance of Nerispirdine (HP184) and AVE5638》.Formula: C12H8N2 The author mentioned the following in the article:

Replacing hydrogen with deuterium as a means of altering ADME properties of drug mols. has recently enjoyed a renaissance, such that at least two deuterated chem. entities are currently in clin. development. Although most research in this area aims to increase the metabolic stability, and hence half-life of the active species, experience has shown that prediction of the in vivo behavior of deuterated mols. is difficult and depends on multiple factors including the complexity of the metabolic scheme, the enzymes involved and hence the mechanism of the rate-determining step in the biotransformation. In an effort to elucidate some of these factors we examined the metabolic behavior of two mols. from the Sanofi portfolio in a range of in vitro and in vivo systems. Although some key metabolic reactions of the acetylcholine release stimulator HP184 4 were slowed in vitro and in vivo when deuterium was present at the sites of metabolism, this did not translate to an increase in overall metabolic stability. By contrast, the tryptase inhibitor AVE5638 13 was much more metabolically stable in vitro in its deuterated form than when unlabeled. These results indicate that it could be of value to concentrate efforts in this area to mols. which are metabolised by a major pathway that involves enzymes of the amine oxidase family or other low-capacity enzyme families. In the experiment, the researchers used many compounds, for example, 3-(Pyridin-4-yl)benzonitrile(cas: 4350-55-4Formula: C12H8N2)

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. Organic compounds containing multiple nitrile groups are known as cyanocarbons.Formula: C12H8N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines》 were Markley, Lowell D.; Tong, Yulan C.; Dulworth, Jacqueline K.; Steward, David L.; Goralski, Christopher T.; Johnston, Howard; Wood, Steven G.; Vinogradoff, Anna P.; Bargar, Thomas M.. And the article was published in Journal of Medicinal Chemistry in 1986. Recommanded Product: 99902-72-4 The author mentioned the following in the article:

Seventy-four title compounds [I; R1 and R2 = e.g. H, 3-, 4-, 5-, or 6-MeSO2, 4-NO2, 2,4-(NO2)2, 4-MeSO2-2-CN, 5-CN, 4-MeO, 4-MeCONH-2-CN, etc.; R3 and R4 = e.g. H, 4-Cl, 3,4-Cl2, 4-COMe, 3,4-(MeO)2, 4-SMe 3-CF3, 4-CN, etc.; and X = CH or N] were prepared, mostly by nucleophilic aromatic substitution reactions of the appropriate phenol with aryl halides with subsequent functional group transformations where necessary, and tested for activity against picornaviruses (rhino- and coxsackie-virus) in vitro; selected I were also tested for protection from coxsackievirus infection in mice. The most active compound, 2-(3,4-dichlorophenoxy)-5-nitrobenzonitrile  [78940-62-2] demonstrated broad-spectrum antipicornavirus activity; this compound and several of its analogs were also effective antiviral agents in vivo. Some structure-activity relations are discussed.6-Phenoxynicotinonitrile(cas: 99902-72-4Recommanded Product: 99902-72-4) was used in this study.

6-Phenoxynicotinonitrile(cas: 99902-72-4) 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. Recommanded Product: 99902-72-4 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

In 2015,Chen, Mao; Ichikawa, Saki; Buchwald, Stephen L. published 《Rapid and Efficient Copper-Catalyzed Finkelstein Reaction of (Hetero)Aromatics under Continuous-Flow Conditions》.Angewandte Chemie, International Edition published the findings.Recommanded Product: 31938-07-5 The information in the text is summarized as follows:

A general, rapid, and efficient method for the copper-catalyzed Finkelstein reaction of (hetero)aromatics has been developed using continuous flow to generate a variety of aryl iodides. The described method can tolerate a broad spectrum of functional groups, including N-H and O-H groups. Addnl., in lieu of isolation, the aryl iodide solutions were used in two distinct multistep continuous-flow processes (amidation and Mg-I exchange/nucleophilic addition) to demonstrate the flexibility of this method. The results came from multiple reactions, including the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Recommanded Product: 31938-07-5)

According to other reports, 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) is used in the preparation of diarylpyrimidines (DAPYs) as HIV-1 non-nucleoside reverse transcriptase inhibitors.Recommanded Product: 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2018,Cao, Qun; Howard, Joseph L.; Wheatley, Emilie; Browne, Duncan L. published 《Mechanochemical Activation of Zinc and Application to Negishi Cross-Coupling》.Angewandte Chemie, International Edition published the findings.SDS of cas: 105942-08-3 The information in the text is summarized as follows:

A form independent activation of zinc, concomitant generation of organozinc species and engagement in a Negishi cross-coupling reaction via mechanochem. methods is reported. The reported method exhibits a broad substrate scope for both C(sp3)-C(sp2) and C(sp2)-C(sp2) couplings and is tolerant to many important functional groups. The method may offer broad reaching opportunities for the in situ generation organometallic compounds from base metals and their concomitant engagement in synthetic reactions via mechanochem. methods. In addition to this study using 4-Bromo-2-fluorobenzonitrile, there are many other studies that have used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3SDS of cas: 105942-08-3) was used in this study.

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.SDS of cas: 105942-08-3 4-Bromo-2-fluorobenzonitrile is also used in the preparation of fluorinated CB2 receptor agonists for PET imaging.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Tuning Molecular Vibrational Energy Flow within an Aromatic Scaffold via Anharmonic Coupling》 were Schmitz, Andrew J.; Pandey, Hari Datt; Chalyavi, Farzaneh; Shi, Tianjiao; Fenlon, Edward E.; Brewer, Scott H.; Leitner, David M.; Tucker, Matthew J.. And the article was published in Journal of Physical Chemistry A in 2019. Application of 17201-43-3 The author mentioned the following in the article:

From guiding chem. reactivity in synthesis or protein folding to the design of energy diodes, intramol. vibrational energy redistribution harnesses the power to influence the underlying fundamental principles of chem. To evaluate the ability to steer these processes, the mechanism and timescales of intramol. vibrational energy redistribution through aromatic mol. scaffolds have been assessed by utilizing two-dimensional IR (2D IR) spectroscopy. 2D IR cross peaks reveal energy relaxation through an aromatic scaffold from the azido- to the cyano- vibrational reporters in p-azidobenzonitrile (PAB) and p-(azidomethyl)benzonitrile (PAMB) prior to energy relaxation into the solvent. The rates of energy transfer are modulated by Fermi resonances, which are apparent by the coupling cross peaks identified within the 2D IR spectrum. Theor. vibrational mode anal. allowed de-termination of the origins of the energy flow, the transfer pathway, and a direct comparison of the associated transfer rates, which were in good agreement with the exptl. results. Large variations in energy transfer rates, approx. 1.9 ps for PAB and 23 ps for PAMB, illustrate the importance of strong anharmonic coupling, i.e. Fermi resonance, on the transfer pathways. In particular, vibrational energy rectification is altered by Fermi resonances of the cyano- and azido- modes allowing control of the propensity for energy flow. After reading the article, we found that the author used 4-Cyanobenzyl bromide(cas: 17201-43-3Application of 17201-43-3)

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.Application of 17201-43-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Pharmacophore-based design of novel 3-hydroxypyrimidine-2,4-dione subtypes as inhibitors of HIV reverse transcriptase-associated RNase H: Tolerance of a nonflexible linker》 were Tang, Jing; Do, Ha T.; Huber, Andrew D.; Casey, Mary C.; Kirby, Karen A.; Wilson, Daniel J.; Kankanala, Jayakanth; Parniak, Michael A.; Sarafianos, Stefan G.; Wang, Zhengqiang. And the article was published in European Journal of Medicinal Chemistry in 2019. Safety of 2-(3-Bromophenyl)acetonitrile The author mentioned the following in the article:

The pharmacophore of active site inhibitors of human immunodeficiency virus (HIV) reverse transcriptase (RT)-associated RNase H typically entails a flexible linker connecting the chelating core and the hydrophobic aromatics We report herein that novel 3-hydroxypyrimidine-2,4-dione (HPD) subtypes with a nonflexible C-6 carbonyl linkage exhibited potent and selective biochem. inhibitory profiles with strong RNase H inhibition at low nM, weak to moderate integrase strand transfer (INST) inhibition at low μM, and no to marginal RT polymerase (pol) inhibition up to 10 μM. A few analogs also demonstrated significant antiviral activity without cytotoxicity. The overall inhibitory profile is comparable to or better than that of previous HPD subtypes with a flexible C-6 linker, suggesting that the nonflexible carbonyl linker can be tolerated in the design of novel HIV RNase H active site inhibitors. The experimental process involved the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Safety of 2-(3-Bromophenyl)acetonitrile)

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.Safety of 2-(3-Bromophenyl)acetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts