Tag: 100-200

In 1980,Journal of Organic Chemistry included an article by Schuster, Ingeborg I.; Roberts, John D.. Category: nitriles-buliding-blocks. The article was titled 《Proximity effects on nitrogen-15 chemical shifts of 8-substituted 1-nitronaphthalenes and 1-naphthylamines》. The information in the text is summarized as follows:

The 15N chem. shifts of several title naphthalenes were determined and, except for high-field shifts observed for 8-cyano- or 8-nitro-1-naphthylamine (I), the substituent effects are unexpectedly small. The high-field shifts of the amine nitrogens of I may indicate complexing between the amino group of the proximate substituents of the type suggested by J. D. Dunitz, (1978). The smallness of the other substituent effects may be the result of mutual cancellation of opposing larger effects. The experimental part of the paper was very detailed, including the reaction process of 5-Amino-1-naphthonitrile(cas: 72016-73-0Category: nitriles-buliding-blocks)

5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime. Large quantities of aliphatic amines are made synthetically. The most widely used industrial method is the reaction of alcohols with ammonia at a high temperature, catalyzed by metals or metal oxide catalysts (e.g., nickel or copper). Mixtures of primary, secondary, and tertiary amines are thereby produced.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
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《Triarylamine-Pyridine-Carbonitriles for Organic Light-Emitting Devices with EQE Nearly 40%》 was written by Chen, Yi-Kuan; Jayakumar, Jayachandran; Hsieh, Chia-Min; Wu, Tien-Lin; Liao, Chun-Cheng; Pandidurai, Jayabalan; Ko, Chang-Lun; Hung, Wen-Yi; Cheng, Chien-Hong. Safety of 3-Oxo-3-phenylpropanenitrileThis research focused ontriarylamine pyridine carbonitrile organic light emitting device photoluminescence; external quantum efficiency of nearly 40%; molecular orientation; operational stability; organic light-emitting diodes; pyridine-carbonitrile; thermally activated delayed fluorescence; triphenylamine. The article conveys some information:

Highly efficient thermally activated delayed fluorescence (TADF) mols. are in urgent demand for solid-state lighting and full-color displays. Here, the design and synthesis of three triarylamine-pyridine-carbonitrile-based TADF compounds, TPAPPC, TPAmPPC, and tTPAmPPC, are shown. They exhibit excellent photoluminescence quantum yields of 79-100% with small ΔEST values, fast reverse intersystem crossing (RISC), and high horizontal dipole ratios (Θ// = 86-88%) in the thin films leading to the enhancement of device light outcoupling. Consequently, a green organic light-emitting diode (OLED) based on TPAmPPC shows a high average external quantum efficiency of 38.8 ± 0.6%, a current efficiency of 130.1 ± 2.1 cd A-1, and a power efficiency of 136.3 ± 2.2 lm W-1. The highest device efficiency of 39.8% appears to be record-breaking among TADF-based OLEDs to date. In addition, the TPAmPPC-based device shows superior operation lifetime and high-temperature resistance. It is worth noting that the TPA-PPC-based materials have excellent optical properties and the potential for making them strong candidates for TADF practical application. In the experiment, the researchers used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Safety of 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.Safety of 3-Oxo-3-phenylpropanenitrile

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《Studies on the N-oxides of π-deficient N-heteroaromatics. XXXIV. Studies on oxazepine derivatives. X. A novel synthesis of substituted indoles by photochemical ring contraction of 3,1-benzoxazepines》 was written by Kaneko, Chikara; Fujii, Harue; Kawai, Shinji; Yamamoto, Atsushi; Hashiba, Kazuhiko; Kimata, Toshihiko; Hayashi, Reiko; Somei, Masanori. Name: 3-Chloro-1H-indole-2-carbonitrile And the article was included in Chemical & Pharmaceutical Bulletin on April 30 ,1980. The article conveys some information:

A novel photochem. ring-contraction reaction of 3,1-benzoxazepines I (R = cyano, Ph; R1 = Cl, CO2H; R2 = H) yields 3-formylindoles II (R3 = CHO, R4 = H, Cl) in an aprotic solvent. This ring contraction was successfully extended to oxazepines having an alkoxycarbonyl function at the 5-position to give the indoles having this function at the 3-position. Though most of the oxazepines underwent the ring-contraction reaction only on irradiation at 254 nm, 5-carboxy derivatives or their esters afforded the ring-contraction products even at ≥300 nm. The intermediacy of 3H-indole species in these photochem. ring-contraction reactions was demonstrated by the isolation of II (R = Ph, R3 = Ac, R4 = 5-CO2Me) during the photolysis of I (R = Ph, R1 = COOMe, R2 = Me) this 3H-indole afforded II (R = Ph, R3 = Ac, R4 = 4-, and 6-CO2Me) upon further irradiation The mechanism of this acetyl migration is discussed based on the result of the photochem. acetyl migration of Me 1-acetyl-2-phenylindole-3-carboxylate. The oxazepines were obtained by photochem. rearrangement of quinoline oxides at ≥300 nm. The experimental process involved the reaction of 3-Chloro-1H-indole-2-carbonitrile(cas: 74960-46-6Name: 3-Chloro-1H-indole-2-carbonitrile)

3-Chloro-1H-indole-2-carbonitrile(cas: 74960-46-6) is a member of organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. They are generally not present in crude oils and are typically the result of additives, cleaning solutions or chemicals used for oil recovery.Name: 3-Chloro-1H-indole-2-carbonitrile

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《High-Performance Ultraviolet Organic Light-Emitting Diode Enabled by High-Lying Reverse Intersystem Crossing》 was written by Zhang, Han; Li, Ganggang; Guo, Xiaomin; Zhang, Kai; Zhang, Bing; Guo, Xuecheng; Li, Yuxuan; Fan, Jianzhong; Wang, Zhiming; Ma, Dongge; Tang, Ben Zhong. Formula: C7H4FNThis research focused onUV organic emitter light emitting diode color purity; OLEDs; UV emission; hybridized local and charge-transfer state; record-high EQE; reverse intersystem crossing. The article conveys some information:

UV organic emitters that can open up applications for future organic light-emitting diodes (OLEDs) are of great value but rarely developed. Here, we report a high-quality UV emitter with hybridized local and charge-transfer (HLCT) excited state and its application in UV OLEDs. The UV emitter, 2BuCz-CNCz, shows the features of low-lying locally excited (LE) emissive state and high-lying reverse intersystem crossing (hRISC) process, which helps to balance the color purity and exciton utilization of UV OLED. Consequently, the OLED based on 2BuCz-CNCz exhibits not only a desired narrowband UV electroluminescent (EL) at 396 nm with satisfactory color purity (CIEx, y=0.161, 0.031), but also a record-high maximum external quantum efficiency (EQE) of 10.79 % with small efficiency roll-off. The state-of-the-art device performance can inspire the design of UV emitters, and pave a way for the further development of high-performance UV OLEDs. In the part of experimental materials, we found many familiar compounds, such as 4-Fluorobenzonitrile(cas: 1194-02-1Formula: 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.Formula: C7H4FN

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Nitrile – Wikipedia,
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Name: 4-FluorobenzonitrileIn 2021 ,《Highly Efficient Oxidative Cyanation of Aldehydes to Nitriles over Se,S,N-tri-Doped Hierarchically Porous Carbon Nanosheets》 was published in Angewandte Chemie, International Edition. The article was written by Hua, Manli; Song, Jinliang; Huang, Xin; Liu, Huizhen; Fan, Honglei; Wang, Weitao; He, Zhenhong; Liu, Zhaotie; Han, Buxing. The article contains the following contents:

A series of Se,S,N-tri-doped carbon nanosheets with a hierarchical porous structure was designed (denoted as Se,S,N-CNs-x, x represented the pyrolysis temperature). It was found that the obtained Se,S,N-CNs-1000 was very selective and efficient for oxidative cyanation of various aldehydes including those containing other oxidizable groups into the corresponding nitriles using ammonia as the nitrogen resource below 100°C. Detailed investigations revealed that the excellent performance of Se,S,N-CNs-1000 originated mainly from the graphitic-N species with lower electron d. and synergistic effect between the Se, S, N and C in the catalyst. Besides, the hierarchically porous structure could also promote the reaction. Notably, the unique feature of this metal-free catalyst was that it tolerated other oxidizable groups and showed no activity on further reaction of the products, thereby resulting in high selectivity. Based on the investigations, this is the first work for the synthesis of nitriles via oxidative cyanation of aldehydes over heterogeneous metal-free catalysts. In addition to this study using 4-Fluorobenzonitrile, there are many other studies that have used 4-Fluorobenzonitrile(cas: 1194-02-1Name: 4-Fluorobenzonitrile) was used in this study.

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.Name: 4-Fluorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

HPLC of Formula: 31938-07-5In 2019 ,《Discovery of Selective, Orally Bioavailable Pyrazolopyridine Inhibitors of Protein Kinase Cθ (PKCθ) That Ameliorate Symptoms of Experimental Autoimmune Encephalomyelitis》 appeared in ACS Medicinal Chemistry Letters. The author of the article were Collier, Philip N.; Twin, Heather C.; Knegtel, Ronald M. A.; Boyall, Dean; Brenchley, Guy; Davis, Christopher J.; Keily, Shazia; Mak, Chau; Miller, Andrew; Pierard, Francoise; Settimo, Luca; Bolton, Clare M.; Chiu, Peter; Curnock, Adam; Doyle, Elisabeth; Tanner, Adam J.; Jimenez, Juan-Miguel. The article conveys some information:

PKCθ plays an important role in T cell biol. and is a validated target for a number of disease states. A series of potent and selective PKCθ inhibitors were designed and synthesized starting from a HTS hit compound Cell activity, while initially a challenge to achieve, was built into the series by transforming the nitrile unit of the scaffold into a primary amine, the latter predicted to form a new hydrogen bond to Asp508 near the entrance of the ATP binding site of PKCθ. Significant improvements in physiochem. parameters were observed on introduction of an oxetane group proximal to a primary amine leading to compound I, which demonstrated a reduction of symptoms in a mouse model of multiple sclerosis. In the experimental materials used by the author, we found 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5HPLC of Formula: 31938-07-5)

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.HPLC of Formula: 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kumar Mehra, Manish; Malik, Monika; Kumar, Bintu; Kumar, Dalip published an article in 2021. The article was titled 《Chemoselective Cu-catalyzed synthesis of diverse N-arylindole carboxamides, β-oxo amides and N-arylindole-3-carbonitriles using diaryliodonium salts》, and you may find the article in Organic & Biomolecular Chemistry.Reference of 3-Oxo-3-phenylpropanenitrile The information in the text is summarized as follows:

Chemoselective copper-catalyzed synthesis of diverse N-arylindole-3-carboxamides, β-oxo amides and N-arylindole-3-carbonitriles from readily accessible indole-3-carbonitriles, α-cyano ketones and diaryliodonium salts has been developed. Diverse N-arylindole-3-carboxamides and β-oxo amides were successfully achieved in high yields under copper-catalyzed neutral reaction conditions, and the addition of an organic base (DIPEA) resulted in a completely different selectivity pattern to produce N-arylindole-3-carbonitriles. Moreover, the importance of the developed methodol. was realized by the synthesis of indoloquinolones and N-((1H-indol-3-yl)methyl)aniline and by a single-step gram-scale synthesis of the naturally occurring cephalandole A analog. In the part of experimental materials, we found many familiar compounds, such as 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Reference of 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.Reference of 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Cascade Cross-Coupling of Dienes: Photoredox and Nickel Dual Catalysis》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Huang, Long; Zhu, Chen; Yi, Liang; Yue, Huifeng; Kancherla, Rajesh; Rueping, Magnus. Formula: C7H4BrN The article mentions the following:

Chem. transformations based on cascade reactions have the potential to simplify the preparation of diverse and architecturally complex mols. dramatically. Herein, the authors disclose an unprecedented and efficient method for the cross-coupling of radical precursors, dienes, and electrophilic coupling partners via a photoredox- and nickel-enabled cascade cross-coupling process. The cascade reaction furnishes a diverse array of saturated carbo- and heterocyclic scaffolds, thus providing access to a quick gain in C-C bond saturation In the experimental materials used by the author, we found 4-Bromobenzonitrile(cas: 623-00-7Formula: C7H4BrN)

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,Formula: C7H4BrN 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

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

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

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Nitrile – Wikipedia,
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