Month: October 2022

Safety of 3-Chloro-4-fluorophenylacetonitrileOn September 25, 2008 ,《Enantiomeric Propanolamines as selective N-Methyl-D-aspartate 2B Receptor Antagonists》 was published in Journal of Medicinal Chemistry. The article was written by Tahirovic, Yesim A.; Geballe, Matthew; Gruszecka-Kowalik, Ewa; Myers, Scott J.; Lyuboslavsky, Polina; Le, Phuong; French, Adam; Irier, Hasan; Choi, Woo-baeg; Easterling, Keith; Yuan, Hongjie; Wilson, Lawrence J.; Kotloski, Robert; McNamara, James O.; Dingledine, Raymond; Liotta, Dennis C.; Traynelis, Stephen F.; Snyder, James P.. The article contains the following contents:

Enantiomeric propanolamines have been identified as a new class of NR2B-selective NMDA receptor antagonists. The most effective agents are biaryl structures, synthesized in six steps with overall yields ranging from 11-64%. The compounds are potent and selective inhibitors of NR2B-containing recombinant NMDA receptors with IC50 values between 30-100 nM. Potency is strongly controlled by substitution on both rings and the centrally located amine nitrogen. SAR anal. suggests that well-balanced polarity and chain-length factors provide the greatest inhibitory potency. Structural comparisons based on 3D shape anal. and electrostatic complementarity support this conclusion. The antagonists are neuroprotective in both in vitro and in vivo models of ischemic cell death. In addition, some compounds exhibit anticonvulsant properties. Unlike earlier generation NMDA receptor antagonists and some NR2B-selective antagonists, the present series of propanolamines does not cause increased locomotion in rodents. Thus, the NR2B-selective antagonists exhibit a range of therapeutically interesting properties. The experimental process involved the reaction of 3-Chloro-4-fluorophenylacetonitrile(cas: 658-98-0Safety of 3-Chloro-4-fluorophenylacetonitrile)

3-Chloro-4-fluorophenylacetonitrile(cas: 658-98-0) 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.Safety of 3-Chloro-4-fluorophenylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhu, Yongbao; Cameron, Beth R.; Skerlj, Renato T. published an article in Journal of Organometallic Chemistry. The title of the article was 《Cycloauration of substituted 2-phenoxypyridine derivatives and X-ray crystal structure of gold, dichloro[2-[[5-[(cyclopentylamino)carbonyl]-2-pyridinyl-κN]oxy]phenyl-κC]-, (SP-4-3)-》.Recommanded Product: 6-Phenoxynicotinonitrile The author mentioned the following in the article:

Direct cycloauration of 2-phenoxypyridines with different substituents at the 5-position of the pyridine ring was carried out in an CH3CN/H2O medium, leading to isolation of cycloaurated compounds AuCl2(L) (HL = substituted 2-phenoxypyridine ligand) with alkyl, substituted alkyl, Ph, halo, ester, and amido groups. Preparation of cycloaurated compounds involved formation of an intermediate AuCl3(HL) via coordination reaction between the pyridine ligand and NaAuCl4 at room temperature and subsequent formation of the Au-C bond at elevated temperature in an CH3CN/H2O medium. The presence of a bulky lipophilic group decreased the yield of cycloaurated compounds and favored decomposition of the reaction species to Au(0). No coordination reaction was observed for ligands with a strong electron-withdrawing substituent (nitro or nitrile) in the pyridine ring. The ligand having the electron-donating dimethylamino group was oxidized by NaAuCl4 at room temperature The presence of a thienyl or an acetyl group allowed the isolation of the intermediate AuCl3(HL), but had an adverse effect on the subsequent cycloauration. The result of direct cycloauration of methyl-substituted 2-phenoxypyridine ligands indicated that the presence of a Me group at the 6-position in the pyridine ring closest to the Au-N(py) bond resulted in poor cycloauration and a decrease in compound stability. The X-ray crystal structure of cycloaurated compound AuCl2L (L = [2-[[5-[(cyclopentylamino)carbonyl]-2-pyridinyl-κN]oxy]phenyl-κC]) 1 was determined, depicting a four-coordinate Au atom located in the center of a slightly distorted square. The results came from multiple reactions, including the reaction of 6-Phenoxynicotinonitrile(cas: 99902-72-4Recommanded Product: 6-Phenoxynicotinonitrile)

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: 6-Phenoxynicotinonitrile 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 2002,Imoto, Hiroshi; Imamiya, Eikoh; Momose, Yu; Sugiyama, Yasuo; Kimura, Hiroyuki; Sohda, Takashi published 《Studies on non-thiazolidinedione antidiabetic agents. 1. Discovery of novel oxyiminoacetic acid derivatives》.Chemical & Pharmaceutical Bulletin published the findings.Electric Literature of C8H6BrN The information in the text is summarized as follows:

A novel series of oxyiminoacetic acid derivatives were synthesized in an effort to develop a potent antidiabetic agent, which does not contain the 2,4-thiazolidinedione moiety. These compounds were evaluated for glucose and lipid lowering effects in genetically obese and diabetic KKAy mice. Several of the compounds showed strong antidiabetic activity, including functional potency at peroxisome proliferator-activated receptor (PPAR)-γ. (Z)-2-[4-[(5-Methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzyloxyimino]-2-(4-phenoxyphenyl)acetic acid (25) significantly reduced plasma glucose (33%, p<0.01) and plasma triglyceride levels (43%, p<0.01) even at a dosage of 0.001% in diet. Pharmacokinetic analyses of 25 are also reported. In the experiment, the researchers used many compounds, for example, 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Electric Literature of C8H6BrN)

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.Electric Literature of C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2008,Cao, Yu-Qing; Zhang, Zhan; Guo, Yan-Xin published 《A practical one-pot conversion of alcohols into homologous nitriles catalyzed by PEG 400 and sodium iodide》.Organic Chemistry: An Indian Journal published the findings.Related Products of 31938-07-5 The information in the text is summarized as follows:

Alcs. were converted into nitriles by one-pot reactions with trimethylchlorosilane and sodium cyanide catalyzed by PEG400 and sodium iodide in dichloromethane in excellent yields.2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Related Products of 31938-07-5) was used in this study.

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.Related Products of 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2018,Li, Jie; Knochel, Paul published 《Cobalt-Catalyzed Cross-Couplings between Alkenyl Acetates and Aryl or Alkenyl Zinc Pivalates》.Angewandte Chemie, International Edition published the findings.Recommanded Product: 4-Bromo-2-fluorobenzonitrile The information in the text is summarized as follows:

CoBr2 (5 mol %) in the presence of 2,2′-bipyridyl (5 mol %) enables electrophilic alkenylations between easily accessible alkenyl acetates or tosylates and various functionalized aryl zinc pivalates at ambient temperature This cobalt-catalyzed process was further applicable to alkenyl zinc pivalates to provide substituted 1,3-dienes. The experimental part of the paper was very detailed, including the reaction process of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Recommanded Product: 4-Bromo-2-fluorobenzonitrile)

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.Recommanded Product: 4-Bromo-2-fluorobenzonitrile 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 2018,Wang, Lei; Tang, Jing; Huber, Andrew D.; Casey, Mary C.; Kirby, Karen A.; Wilson, Daniel J.; Kankanala, Jayakanth; Parniak, Michael A.; Sarafianos, Stefan G.; Wang, Zhengqiang published 《6-Biphenylmethyl-3-hydroxypyrimidine-2,4-diones potently and selectively inhibited HIV reverse transcriptase-associated RNase H》.European Journal of Medicinal Chemistry published the findings.Application of 31938-07-5 The information in the text is summarized as follows:

Herein the design, synthesis, biochem. and antiviral evaluations of a new 6-biphenylmethyl subtype of the 3-hydroxypyrimidine-2,4-dione (HPD) chemotype is reported. In biochem. assays, analogs of this new subtype potently inhibited RT RNase H in low nanomolar range without inhibiting RT polymerase (pol) or integrase strand transfer (INST) at the highest concentrations tested. In cell-based assays, a few analogs inhibited HIV in low micromolar range without cytotoxicity at concentrations up to 100 μM. In the experiment, the researchers used many compounds, for example, 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Application of 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.Application of 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2019,Journal of the American Chemical Society included an article by Li, Jie; Tan, Eric; Keller, Niklas; Chen, Yi-Hung; Zehetmaier, Peter M.; Jakowetz, Andreas C.; Bein, Thomas; Knochel, Paul. Electric Literature of C7H3BrFN. The article was titled 《Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines》. The information in the text is summarized as follows:

The reaction of various organozinc pivalates with anthranils provides anilines derivatives, which cyclize under acidic conditions providing condensed quinolines. Using alkenylzinc pivalates, electron-rich arylzinc pivalates or heterocyclic zinc pivalates produces directly the condensed quinolines of which several structures belong to new heterocyclic scaffolds. These N-heterocycles are of particular interest for organic light emitting diodes with their high photoluminescence quantum yields and long exciton lifetimes as well as for hole-transporting materials in methylammonium lead iodide perovskites solar cells due to an optimal band alignment for holes and a large bandgap. The experimental process involved the reaction of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Electric Literature 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.Electric Literature 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

The author of 《Impregnated copper ferrite on mesoporous graphitic carbon nitride: An efficient and reusable catalyst for promoting ligand-free click synthesis of diverse 1,2,3-triazoles and tetrazoles》 were Khalili, Dariush; Rezaee, Meysam. And the article was published in Applied Organometallic Chemistry in 2019. Computed Properties of C8H6BrN The author mentioned the following in the article:

Synthesis of magnetic CuFe2O4/g-C3N4 hybrids via a facile method and their catalytic performances were evaluated via click chem. was reported. The structural and morphol. characterization of CuFe2O4, g-C3N4, CuFe2O4/g-C3N4 were carried out by different techniques such as X-ray diffraction, high-resolution transmission electron microscopy, field emission SEM, Fourier IR spectroscopy, vibrating sample magnetometry, thermogravimetric anal. and N2 adsorption-desorption anal. (Brunauer-Emmett-Teller surface area). The utilization of magnetic CuFe2O4/g-C3N4 enabled superior performance in the one-pot azide-alkyne cycloaddition reaction in water using alkyl halides and epoxides as azide precursors without the need of any addnl. agents to afford triazoles I [R = cyclohexyl, allyl, Bn, etc.; Ar = Ph, 2-methoxynaphthalenyl] and II [Ar1 = Ph, 2-methoxynaphthalenyl; R1 = H, Ph, 4-ClC6H4; R2 = H, Et, CH2OPh, etc.]. Also 5-substituted 1H-tetrazoles III [Ar2 = Ph, 4-MeC6H4, 2-ClC6H4, etc.] were prepared via [3 + 2] cycloaddition of sodium azide and aryl nitriles by using magnetic CuFe2O4/g-C3N4 nanoparticles. In addition, the catalytic system highly fulfilled the demands of “”green click chem.”” with its convenient conditions, especially easy access to a variety of significant products in low catalyst loading and simple work-up and isolation procedure.4-Cyanobenzyl bromide(cas: 17201-43-3Computed Properties of C8H6BrN) was used in this study.

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.Computed Properties of C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Synthesis of α-Ketoamides from β-Ketonitriles and Primary Amines: A Catalyst-Free Oxidative Decyanation-Amidation Reaction》 were Zhang, Ya-Kai; Wang, Bin. And the article was published in European Journal of Organic Chemistry in 2019. Recommanded Product: 3-Oxo-3-phenylpropanenitrile The author mentioned the following in the article:

AN oxidative decyanation-amidation of β-ketonitriles and primary amines readily occurs using hydrogen peroxide sodium carbonate adduct (Na2CO3·1.5H2O2), K2CO3, and 1,4-dioxane. This reaction affords α-ketoamides under mild conditions without the need of a catalyst. In the experiment, the researchers used many compounds, for example, 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Recommanded Product: 3-Oxo-3-phenylpropanenitrile)

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.Recommanded Product: 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Rational Design of an Organocatalyst for Peptide Bond Formation》 were Handoko; Satishkumar, Sakilam; Panigrahi, Nihar R.; Arora, Paramjit S.. And the article was published in Journal of the American Chemical Society in 2019. Product Details of 105942-08-3 The author mentioned the following in the article:

Amide bonds are ubiquitous in peptides, proteins, pharmaceuticals and polymers. The formation of amide bonds is a relatively straightforward process: amide bonds can be synthesized with relative ease because of the availability of efficient coupling agents. However, there is a substantive need for methods that do not require excess reagents. A catalyst that condenses amino acids could have an important impact by reducing the significant waste generated during peptide synthesis. We describe the rational design of a biomimetic catalyst that can efficiently couple amino acids featuring standard protecting groups. The catalyst design combines lessons learned from enzymes, peptide biosynthesis, and organocatalysts. Under optimized conditions, 5 mol% catalyst efficiently couples Fmoc (Fmoc = 9-fluorenyl methoxycarbonyl) amino acids without significant racemization. Significantly, we demonstrate that the catalyst is functional for the synthesis of oligopeptides on solid phase. This result is significant because it illustrates the potential of the catalyst to function on a substrate with a multitude of amide bonds, which may be expected to inhibit a hydrogen bonding catalyst. In the experimental materials used by the author, we found 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Product Details of 105942-08-3)

4-Bromo-2-fluorobenzonitrile(cas:105942-08-3) is used as a OLED intermediate, Pharmaceutical, electronic and chemical intermediate.Product Details of 105942-08-3 It is used in the synthesis of heterocycles and liquid crystals.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts