October 2022 - Page 131 of 136 - Nitriles-buliding-blocks

Wu, Yong’s team published research in Proceedings of the National Academy of Sciences of the United States of America in 2022 | CAS: 17201-43-3

4-Cyanobenzyl bromide(cas: 17201-43-3) is used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile. It is also useful in the preparation of 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile by reaction with 2H-tetrazole in the presence of potassium hydroxide.Synthetic Route of C8H6BrN

In 2022,Wu, Yong; Guo, Qing-Hui; Qiu, Yunyan; Weber, Jacob A.; Young, Ryan M.; Bancroft, Laura; Jiao, Yang; Chen, Hongliang; Song, Bo; Liu, Wenqi; Feng, Yuanning; Zhao, Xingang; Li, Xuesong; Zhang, Long; Chen, Xiao-Yang; Li, Hao; Wasielewski, Michael R.; Stoddart, J. Fraser published an article in Proceedings of the National Academy of Sciences of the United States of America. The title of the article was 《Syntheses of three-dimensional catenanes under kinetic control》.Synthetic Route of C8H6BrN The author mentioned the following in the article:

Although catenanes comprising two ring-shaped components can be made in large quantities by templation, the preparation of three-dimensional (3D) catenanes with cage-shaped components is still in its infancy. Here, the design and syntheses of two 3D catenanes by a sequence of SN2 reactions in one pot is reported. The resulting triply mech. interlocked mols. were fully characterized in both the solution and solid states. Mechanistic studies have revealed that a suit[3]ane, which contains a threefold sym. cage component as the suit and a tribromide component as the body, is formed at elevated temperatures This suit[3]ane was identified as the key reactive intermediate for the selective formation of the two 3D catenanes which do not represent thermodn. min. This particular synthetic strategy might be used in the future to guide the rational design and production of mech. interlocked mols. under kinetic control. The experimental part of the paper was very detailed, including the reaction process of 4-Cyanobenzyl bromide(cas: 17201-43-3Synthetic Route of C8H6BrN)

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wang, Yanhui’s team published research in Journal of Materials Chemistry C: Materials for Optical and Electronic Devices in 2019 | 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.Category: nitriles-buliding-blocks

In 2019,Journal of Materials Chemistry C: Materials for Optical and Electronic Devices included an article by Wang, Yanhui; Zhang, Zhenzhen; Liu, Linxi; Yuan, Shou; Ma, Jie; Liu, Danfeng; Xue, Shanfeng; Sun, Qikun; Yang, Wenjun. Category: nitriles-buliding-blocks. The article was titled 《Cyanophenylcarbazole isomers exhibiting different UV and visible light excitable room temperature phosphorescence》. The information in the text is summarized as follows:

Pure organic luminophores with room temperature phosphorescence (RTP) have been attracting much attention due to their potential applications and academic importance. The development of such materials with visible light-excitability and the understanding of the structure-property relationship are highly desirable. In the current work, the five structural isomers of cyano-substituted phenylcarbazoles with cyano at the para-, meta-, and ortho-position of the Ph ring (PCN, MCN and OCN) and the 2- and 3-position of the carbazole ring (2CN, 3CN) are systematically designed and synthesized. These crystals all have RTP activity under 365 nm UV and 400-460 nm visible light excitation but exhibit different RTP intensities and lifetimes. The crystal packing anal. and quantum chem. calculations as well as low temperature phosphorescence measurements indicate that cyano substitution can greatly enhance intermol. CH···N and CH···π interactions and increase inter-system crossing probability, but the structural isomerism can significantly affect the oxygen quenching effect on RTP. Moreover, 2CN and 3CN crystals with H-aggregation are more favorable for the visible-light excitable RTP. These findings indicate that structural isomerism can tune the crystal packing modes and the visible-light excitable RTP as well as the existence of the direct triplet state population from the ground state. In the experimental materials used by the author, we found 4-Fluorobenzonitrile(cas: 1194-02-1Category: nitriles-buliding-blocks)

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kasina, Krishna Chaitanya’s team published research in Chemistry of Heterocyclic Compounds (New York, NY, United States) in 2021 | CAS: 2042-37-7

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. This substrate molecule undergoes a palladium-catalyzed coupling reaction to form an aromatic ring. The light emission from this reaction can be seen in the reaction solution.HPLC of Formula: 2042-37-7

Kasina, Krishna Chaitanya; Rapeti, Siva Kumar; Sadhukhan, Arghya; Ranga, Mahesh; Pal, Arani; Birudaraju, Saritha; Tirukkovalluri, Siva rao published their research in Chemistry of Heterocyclic Compounds (New York, NY, United States) in 2021. The article was titled 《Silver-assisted palladium-catalyzed one-pot synthesis of 3-(hetero)arylmethyl derivatives of imidazo[1,2-a]pyridines》.HPLC of Formula: 2042-37-7 The article contains the following contents:

3-(Hetero)arylmethyl derivatives of imidazo[1,2-a]pyridine were synthesized by a novel one-pot method consisting of the Sonogashira coupling of tert-Bu prop-2-yn-1-yl(pyridin-2-yl)carbamate with different substituted (hetero)aryl bromides and cyclization of the in-situ obtained intermediate substituted (hetero)aryl acetylene derivatives In the experimental materials used by the author, we found 2-Bromobenzonitrile(cas: 2042-37-7HPLC of Formula: 2042-37-7)

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Jang, Ji Seon’s team published research in Journal of Materials Chemistry C: Materials for Optical and Electronic Devices in 2019 | CAS: 614-16-4

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.Related Products of 614-16-4

Related Products of 614-16-4In 2019 ,《Electrostatic potential dispersing pyrimidine-5-carbonitrile acceptor for high efficiency and long lifetime thermally activated delayed fluorescence organic light-emitting diodes》 appeared in Journal of Materials Chemistry C: Materials for Optical and Electronic Devices. The author of the article were Jang, Ji Seon; Lee, Ha Lim; Lee, Kyung Hyung; Lee, Jun Yeob. The article conveys some information:

Pyrimidine-5-carbonitrile was developed as an electrostatic potential managing and strong acceptor moiety of thermally activated delayed fluorescence (TADF) emitters for high efficiency and long lifetime in devices. Two types of TADF emitters with the donor moiety extended from either the 2 or 4 position of the acceptor moiety were prepared to study the effect of the donor substitution position on the TADF characteristics of the TADF emitters. Comparison of the two types of TADF emitters suggested that the extension of the donor structure from the 4 position of the pyrimidine-5-carbonitrile acceptor is an effective way of enhancing the external quantum efficiency (EQE) and lifetime of the TADF devices. A high EQE of 19.8% and lifetime exceeding that of the state-of-the-art green TADF emitter were demonstrated using one of the pyrimidine-5-carbonitrile derived emitters through the uniformly distributed electrostatic potential. The experimental process involved the reaction of 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Related Products of 614-16-4)

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Liu, Xiaoqing’s team published research in Journal of Materials Chemistry C: Materials for Optical and Electronic Devices in 2021 | CAS: 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.Recommanded Product: 2-(3-Bromophenyl)acetonitrile

Recommanded Product: 2-(3-Bromophenyl)acetonitrileIn 2021 ,《Pure room temperature phosphorescence emission of an organic host-guest doped system with a quantum efficiency of 64%》 appeared in Journal of Materials Chemistry C: Materials for Optical and Electronic Devices. The author of the article were Liu, Xiaoqing; Dai, Wenbo; Qian, Junjie; Lei, Yunxiang; Liu, Miaochang; Cai, Zhengxu; Huang, Xiaobo; Wu, Huayue; Dong, Yuping. The article conveys some information:

A new doped system with pure phosphorescent emission is constructed using four 1-(4-(diphenylamino)phenyl)-2-phenylethan-1-one derivatives containing halogen atoms as the guests and benzophenone as the host. That is, the doped system has only phosphorescence emission while almost no fluorescence emission and the phosphorescence quantum efficiency reaches up to 64%. Moreover, the ISC efficiency of excitons can be adjusted by changing the excitation wavelength, so the doped materials can selectively emit green phosphorescence or cyan fluorescence.2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Recommanded Product: 2-(3-Bromophenyl)acetonitrile) was used in this study.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wei, Xiaofang’s team published research in Journal of Materials Chemistry C: Materials for Optical and Electronic Devices in 2017 | CAS: 105942-08-3

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

Safety of 4-Bromo-2-fluorobenzonitrileIn 2017 ,《Triplet decay-induced negative temperature dependence of the transient photoluminescence decay of thermally activated delayed fluorescence emitter》 was published in Journal of Materials Chemistry C: Materials for Optical and Electronic Devices. The article was written by Wei, Xiaofang; Chen, Yongzhen; Duan, Ruihong; Liu, Jianjun; Wang, Ruifang; Liu, Yanwei; Li, Zhiyi; Yi, Yuanping; Yamada-Takamura, Yukiko; Wang, Pengfei; Wang, Ying. The article contains the following contents:

The photophys. properties of three TX-based D-A isomers (TXO-PhCz1, TXO-PhCz3, and TXO-PhCz4) with a PhCz donor at different substitution positions of Ph group on a TXO unit were studied. The substitution position of the PhCz unit significantly impacts the photophys. properties of these isomers. TXO-PhCz1 exhibits a very weak emission in both undoped and doped films, while TXO-PhCz3 and TXO-PhCz4 exhibit a strong emission with the requisite properties for TADF emitters, including a small ΔEST and transient PL decay curves with a prompt and delayed fluorescent component. TXO-PhCz4 exhibits a much stronger orbital coupling than TXO-PhCz3 and then the phosphorescent emission causes the inverse temperature dependence of the transient PL decay, which is contrary to that of TXO-PhCz3 and other TADF emitters. TXO-PhCz4 exhibits a small ΔEST of 23 meV and a short decay time of 14 μs at room temperature, which are much smaller and shorter than those of TXO-PhCz3. Multilayer OLEDs based on TXO-PhCz4 exhibit a very low-efficiency roll-off with a maximum current efficiency of 49.2 cd A-1, a maximum power efficiency of 47.7 lm W-1, and a maximum EQE of 16.3%. In the experiment, the researchers used 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Safety of 4-Bromo-2-fluorobenzonitrile)

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Fan, Zhenhua’s team published research in Tetrahedron in 2019-02-15 | 38487-85-3

Tetrahedron published new progress about Aromatic nitriles Role: RCT (Reactant), RACT (Reactant or Reagent) (2-aminobenzonitriles). 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, Synthetic Route of 38487-85-3.

Fan, Zhenhua; Yang, Shanxue; Peng, Xin; Zhang, Cheng; Han, Jing; Chen, Jie; Deng, Hongmei; Shao, Min; Zhang, Hui; Cao, Weiguo published the artcile< Metal-free synthesis of 2-difluoromethylated quinolines via DBU-promoted cascade michael addition / cyclization of methyl-4,4-difluorobut-2-ynoate with 2-aminobenzonitriles>, Synthetic Route of 38487-85-3, the main research area is difluoromethylated quinoline preparation DBU michael cyclization methyl difluorobutynoate aminobenzonitrile.

A facile synthesis of 2-difluoromethylated quinolines via DBU-promoted cascade Michael addition/cyclization between functionalized 2-aminobenzonitriles and Me 4,4-difluorobut-2-ynoate was developed. Various highly functionalized quinolines were assembled in moderate to good yields under mild metal-free reaction conditions.

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Jia, Qianfa’s team published research in Asian Journal of Organic Chemistry in 2021-08-31 | 21667-62-9

Asian Journal of Organic Chemistry published new progress about [4+2] Cycloaddition reaction (regioselective). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Reference of 21667-62-9.

Jia, Qianfa; Yin, Guoliang; Lan, Yunfei; Lin, Yinhe; Ren, Qiao published the artcile< Base-mediated Benzannulation Reactions for the Synthesis of Densely Functionalized Aryl α-Keto Esters>, Reference of 21667-62-9, the main research area is phenyl keto ester preparation; cyano phenyl methanone ynedione regioselective cycloaddition.

A novel and straightforward strategy for the construction of versatile densely functionalized aryl α-keto esters were disclosed through a one-pot and efficient [4+2] benzannulation reaction of α-cyano-β-methylenones and ynediones, which were synthesized easily from the corresponding starting materials. This protocol featured high yield, mild metal-free reaction condition, high atom economy, high functional-group tolerance, easy handing and gram-scale synthesis.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Yukawa, Tomoya’s team published research in Bioorganic & Medicinal Chemistry in 2016-08-15 | 89324-17-4

Bioorganic & Medicinal Chemistry published new progress about Antidiuretics. 89324-17-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H4N2O, Category: nitriles-buliding-blocks.

Yukawa, Tomoya; Nakada, Yoshihisa; Sakauchi, Nobuki; Kamei, Taku; Yamada, Masami; Ohba, Yusuke; Fujimori, Ikuo; Ueno, Hiroyuki; Takiguchi, Maiko; Kuno, Masako; Kamo, Izumi; Nakagawa, Hideyuki; Fujioka, Yasushi; Igari, Tomoko; Ishichi, Yuji; Tsukamoto, Tetsuya published the artcile< Design, synthesis, and biological evaluation of a novel series of peripheral-selective noradrenaline reuptake inhibitors - Part 3>, Category: nitriles-buliding-blocks, the main research area is crystal structure noradrenaline reuptake inhibitor urinary incontinence; 7-Aryl-1,4-oxazepane derivatives; Intramolecular hydrogen bond; MDR1 efflux ratio; Peripheral-selective noradrenaline reuptake inhibitor; Stress urinary incontinence.

Peripheral-selective inhibition of noradrenaline reuptake is a novel mechanism for the treatment of stress urinary incontinence to overcome adverse effects associated with central action. Here, the authors describe the medicinal chem. approach to discover a novel series of highly potent, peripheral-selective, and orally available noradrenaline reuptake inhibitors with a low multidrug resistance protein 1 (MDR1) efflux ratio by cyclization of an amide moiety and introduction of an acidic group. The authors observed that the MDR1 efflux ratio was correlated with the pKa value of the acidic moiety. The resulting compound I exhibited favorable PK profiles, probably because of the effect of intramol. hydrogen bond, which was supported by a its single-crystal structure. Compound I, which exhibited peripheral NET-selective inhibition at tested doses in rats by oral administration, increased urethral resistance in a dose-dependent manner.

Referemce:
Nitrile – Wikipedia,
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Yadav, Maruti B’s team published research in Tetrahedron Letters in 2022-05-25 | 21667-62-9

Tetrahedron Letters published new progress about Aryl ketones Role: RCT (Reactant), RACT (Reactant or Reagent) (cyano). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Synthetic Route of 21667-62-9 .

Yadav, Maruti B.; Bhosle, Suresh R.; Jeong, Yeon Tae published the artcile< DBU-promoted synthesis of novel heterocyclic [4.3.3] propellanes from α-cyanoketones and cyclic α-diketones>, Synthetic Route of 21667-62-9 , the main research area is heterocyclic tetrahydro benzofuran propellane preparation chemoselective diastereoselective one pot; cyclic alpha diketone cyanoketone multicomponent DBU catalyst.

An effective base-catalyzed Knoevenagel, Michael and intramol./Paal-Knorr cyclization strategy for the construction of heterocyclic [4.3.3] tetrahydro epoxyetheno benzo-furan propellanes (TEBFs) from cyclic α-diketones and α-cyanoketones is reported through single-step reaction. The reaction proceeds under mild reaction conditions and shows excellent chemo and diastereoselectivity in the absence of any external transition metal and ligands. The one-pot two-component procedure also shows the merits of straightforward reaction conditions, simple operation, using available feedstock, wide substrate scope, and high atom and step economy. This reaction provides facile access to highly substituted fused tetrahydro furo-furan propellanes, which can be used in the field of chem. and pharmaceutical research.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts