Month: October 2022

Reference of 4-Cyanobenzyl bromideIn 2022 ,《Photocatalytic activity of ultrathin 2DPNs for enzymatically generating formic acid from CO2 and C-S/C-N bond formation》 appeared in Sustainable Energy & Fuels. The author of the article were Singh, Pooja; Yadav, Rajesh K.; Singh, Chandani; Chaubey, Surabhi; Singh, Satyam; Singh, Atul P.; Baeg, Jin-OoK.; Kim, Tae Wu; Gulzhian, Dzhardimalieva. The article conveys some information:

The exploration of efficient and cheap photocatalysts for the transformation of CO2 into value-added chems. is a cornerstone challenge in organic chem. Two-dimensional covalent organic frameworks (2D-COFs) have attracted a great deal of increasing demand in the field of photocatalysis. Here, we report the design and development of two-dimensional porphyrin nanoplates (2DPNs) as low-cost and highly efficient photocatalysts. The construction of 2DPNs was achieved by the reaction of 5,10,15,20-tetraphenylporphyrin (TPP) building block units via a one-pot Friedel-Crafts reaction. The study revealed that the resultant photocatalyst has many useful properties of a better catalyst such as the superb solar light-harvesting ability, suitability of the optical band-gap, and highly ordered π-electron channels facilitating efficient charge migrations. Further study provides the better utility of 2DPN photocatalysts in the generation of solar fine chems. via the formation of C-S and C-N bonds under solar light irradiation with excellent reusability property. Furthermore, the 2DPN photocatalysts have been efficiently used as catalysts in the CO2 fixation and generation of formic acid as a green energy source under metal-free conditions. The experimental part of the paper was very detailed, including the reaction process of 4-Cyanobenzyl bromide(cas: 17201-43-3Reference of 4-Cyanobenzyl bromide)

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.Reference of 4-Cyanobenzyl bromide

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HPLC of Formula: 1194-02-1In 2019 ,《A BEt3-Base Catalyst for Amide Reduction with Silane》 appeared in Journal of Organic Chemistry. The author of the article were Yao, Wubing; Fang, Huaquan; He, Qiaoxing; Peng, Dongjie; Liu, Guixia; Huang, Zheng. The article conveys some information:

Reported herein is the development of a simple but practical catalytic system for the selective reduction of amides with hydrosilane or hydrosiloxane. Low-cost and readily available triethylborane (1.0 M in THF), in combination with a catalytic amount of an alkali metal base, was found to catalyze the reduction of all three amide classes (tertiary, secondary, and primary amides) to form amines under mild conditions. In addition, the selective transformation of secondary amides to aldimines and primary amides to nitriles can also be achieved by using a proper combination of BEt3 and base. The scope of these BEt3-base-catalyzed amide hydrosilylation reactions has been explored in depth. Preliminary results of mechanistic studies suggest a modified Piers’ silane Si-H···B activation mode wherein the hydride abstraction by BEt3 is promoted by the coordination of an alkoxide or hydroxide anion to the Si center. In the part of experimental materials, we found many familiar compounds, such as 4-Fluorobenzonitrile(cas: 1194-02-1HPLC of Formula: 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.HPLC of Formula: 1194-02-1

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Computed Properties of C9H13NO2On May 31, 2020, de Azambuja, Francisco; Yang, Ming-Hsiu; Feoktistova, Taisiia; Selvaraju, Manikandan; Brueckner, Alexander C.; Grove, Markas A.; Koley, Suvajit; Cheong, Paul Ha-Yeon; Altman, Ryan A. published an article in Nature Chemistry. The article was 《Connecting remote C-H bond functionalization and decarboxylative coupling using simple amines》. The article mentions the following:

Transition metal-catalyzed C-H functionalization and decarboxylative coupling are two of the most notable synthetic strategies developed in the past 30 years. Here, we connect these two reaction pathways using bases and a simple Pd-based catalyst system to promote a para-selective C-H functionalization reaction from benzylic electrophiles [e.g., I → II (82%, 75% isolated) in presence of Pd(PPh3)4 and Et3N in toluene at 110°]. Exptl. and computational mechanistic studies suggest a pathway that involves an uncommon Pd-catalyzed dearomatization of the benzyl moiety followed by a base-enabled rearomatization through a formal 1,5-hydrogen migration. This reaction complements ‘C-H activation’ strategies that convert inert C-H bonds into C-metal bonds prior to C-C bond formation. Instead, this reaction exploits an inverted sequence and promotes C-C bond formation prior to deprotonation. These studies provide an opportunity to develop general para-selective C-H functionalization reactions from benzylic electrophiles and show how new reactive modalities may be accessed with careful control of the reaction conditions. The experimental part of the paper was very detailed, including the reaction process of Ethyl 1-cyanocyclopentane-1-carboxylate(cas: 28247-14-5Computed Properties of C9H13NO2)

Ethyl 1-cyanocyclopentane-1-carboxylate(cas: 28247-14-5) is a member of cyclopentanes. Although cyclopentane itself doesn’t have a single highly favoured conformation, a substituent on the cyclopentane ring can upset the balance of strains thereby favouring either the envelope or the half-chair.Computed Properties of C9H13NO2

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In 2020,Liquid Crystals included an article by Moura Ramos, Joaquim J.; Diogo, Herminio P.. Recommanded Product: 4-Cyano-3-fluorophenyl 4-butylbenzoate. The article was titled 《Phase behavior and slow molecular dynamics in the glassy state and in the glass transformation of a nematic liquid crystal: 4CFPB》. The information in the text is summarized as follows:

The mol. mobility in 4-cyano-3-fluorophenyl 4-butylbenzoate (4CFPB), a nematic liquid crystal, was studied by differential scanning calorimetry (DSC) and thermally stimulated depolarization currents (TSDC). By TSDC a complex behavior was observed in which the main relaxation, with a wide distribution of activation energies, coalesces at high temperature with a poorly distributed mobility; this observation is in line with what was found by dielec. spectroscopy where a ‘double relaxation’ was observed The step signal of the positional glass transition in DSC is a single and clean signal, which shows no evidence of the complexity revealed by the dielec. techniques; this signal seems to correspond to the usual main relaxation. The dynamic fragility values obtained by DSC and by TSDC indicate that 4CFPB is a moderately fragile glass former, in reasonable agreement with the values obtained by dielec. spectroscopy. Among the secondary relaxations in 4CFPB there are modes sensitive to phys. aging, which makes them candidates for Johari-Goldstein’s relaxation status. It is emphasized, however, that this sensitivity to aging may not be a sufficient criterion for the attribution of this quality. In the experimental materials used by the author, we found 4-Cyano-3-fluorophenyl 4-butylbenzoate(cas: 86776-52-5Recommanded Product: 4-Cyano-3-fluorophenyl 4-butylbenzoate)

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).Recommanded Product: 4-Cyano-3-fluorophenyl 4-butylbenzoate

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2020,Organic Chemistry Frontiers included an article by Xiao, Qiang; Liu, Jin; Nie, Jia-Hui; Kong, Ling-Bin; Lin, Jun; Yan, Sheng-Jiao. Application of 50743-32-3. The article was titled 《Silver-catalyzed cascade reactions of 3-cyanochromone with 1,1-enediamines: synthesis of highly functionalized 2-(pyridin-3-yl)-chromeno[2,3-d]pyrimidines》. The information in the text is summarized as follows:

A novel protocol for the construction of highly functionalized 2-(pyridin-3-yl)-chromeno[2,3-d]pyrimidines I [R = H, Me, Cl, Br, i-Pr; R1 = Me, Ph, 4-ClC6H4(CH2)2, etc.] (PCPMDs) from 3-cyanochromones with 1,1-enediamines via an unprecedented cascade reaction was developed by simply refluxing under the catalysis of silver carbonate. As a result, a series of 2-(pyridin-3-yl)-chromeno[2,3-d]pyrimidines I was obtained through a novel cascade reaction involving an amazing electrocyclization mechanism of a cyano group with α,β-unsaturated nitriles. This reaction formation of compounds I was accompanied by the formation of four bonds and the cleavage of one bond in one step. This protocol could be used for the synthesis of various pyridin-3-yl-substituted complex pyrimidine derivatives, and it was suitable for combinatorial and parallel synthesis of PCPMD drugs or natural-like products. In the experiment, the researchers used 6-Isopropyl-4-oxo-4H-chromene-3-carbonitrile(cas: 50743-32-3Application of 50743-32-3)

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. Application of 50743-32-3 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.

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Shen, Yan-Ming; Song, Lin-Lin; Qian, Xu-Hong; Yang, You-Jun published an article on January 31 ,2013. The article was titled 《A scalable synthesis of 1-amino-5-cyanonaphthalene, a precursor for a nitric oxide probe (NO550) designed via the dye assembly principle》, and you may find the article in Chinese Chemical Letters.Application of 72016-73-0 The information in the text is summarized as follows:

A convenient and scalable synthesis of 1-amino-5-cyanonaphthalene was described. In the experimental materials used by the author, we found 5-Amino-1-naphthonitrile(cas: 72016-73-0Application of 72016-73-0)

5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime.Typically the presence of an amine functional group is deduced by a combination of techniques, including mass spectrometry as well as NMR and IR spectroscopies. 1H NMR signals for amines disappear upon treatment of the sample with D2O. In their infrared spectrum primary amines exhibit two N-H bands, whereas secondary amines exhibit only one.Application of 72016-73-0

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Su, Ting; Naughton, Mary Ann H.; Smyth, Mark S.; Rose, Jack W.; Arfsten, Ann E.; McCowan, Jefferson R.; Jakubowski, Joseph A.; Wyss, Virginia L.; Ruterbories, Kenneth J.; Sall, Daniel J.; Scarborough, Robert M. published their research in Journal of Medicinal Chemistry on December 19 ,1997. The article was titled 《Fibrinogen Receptor (GPIIb-IIIa) Antagonists Derived from 5,6-Bicyclic Templates. Amidinoindoles, Amidinoindazoles, and Amidinobenzofurans Containing the N-α-Sulfonamide Carboxylic Acid Function as Potent Platelet Aggregation Inhibitors》.Synthetic Route of C10H6N2O The article contains the following contents:

A series of highly potent and specific fibrinogen receptor antagonists have been discovered and optimized through structural modification of novel amidinoindole and benzofuran compounds Systematic linker optimization afforded the amidinobenzofuran-containing inhibitor 3-[[3-(5-amidino-2-benzofurancarboxamido)propionyl]amino]-3-phenylpropionic acid (I), which displayed an IC50 value of 250 nM in platelet aggregation assays. Attempts to enhance activity by modifying the β-position of β-alaninate of inhibitor I had only a modest effect on inhibitory activity in aggregation assays. Analogs prepared to enhance the activity by conformational restriction were also found to be equally or less potent. In contrast, modification at the α-position of β-alaninate resulted in the identification of extremely potent and novel amidinobenzofuran-containing derivatives Reexamination of 5,6-bicyclic aromatic nucleus led to the further identification of amidinoindole- and amidinoindazole-containing derivatives These analogs exhibited potent in vitro activity with IC50 values of 25-65 nM in platelet aggregation assays and an IC50 value of 2 nM in fibrinogen binding assays and demonstrated a selectivity of >50,000-fold for GPIIb-IIIa vs. the most closely related integrin, the vitronectin receptor, αvβ3. In the experiment, the researchers used 3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9Synthetic Route of C10H6N2O)

3-Formyl-1H-indole-6-carbonitrile(cas: 83783-33-9) is a member of nitriles. Nitriles have been reduced to amines by many methods, especially by catalytic hydrogenation and by metal hydrides. Aliphatic and aromatic nitriles have also been reduced to nitro derivatives using hydrazinium monoformate in the presence of Raney-nickel.Synthetic Route of C10H6N2O

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The author of 《Multi-component reaction to access a library of polyfunctionally substituted 4,7-dihydropyrazolo[3,4-b]pyridines》 were Aggarwal, Ranjana; Kumar, Suresh; Singh, Gulshan. And the article was published in Synthetic Communications in 2019. Formula: C9H7NO The author mentioned the following in the article:

A practical approach to polyfunctionally substituted 4,7-dihydropyrazolo[3,4-b]pyridine derivatives from heteroaryl hydrazine, 3-aryl-3-oxopropanenitriles and aldehydes have been described in the report. The present catalyst-free protocol involves the intermediacy of 5-aminopyrazole and α-cyanochalcone, which undergoes in situ Michael addition to afford title compounds in moderate to good yields. All the steps were conducted concomitantly to render the procedure as practical and straightforward as possible. The expeditious synthetic protocol experiment takes less than one hour and shows broad substrate scope. In the part of experimental materials, we found many familiar compounds, such as 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Formula: C9H7NO)

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.Formula: C9H7NO

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The author of 《Late-Stage Diversification of Imidazole-Based Pharmaceuticals through Pd-Catalyzed Regioselective C-H Bond Arylations》 were Benzai, Amal; Shi, Xinzhe; Derridj, Fazia; Roisnel, Thierry; Doucet, Henri; Soule, Jean-Francois. And the article was published in Journal of Organic Chemistry in 2019. Synthetic Route of C7H4BrN The author mentioned the following in the article:

Palladium-catalyzed C-H bond arylation of imidazoles has been applied to pharmaceuticals such as Bifonazole, Climbazole, and Ketoconazole. In the presence of phosphine-free Pd(OAc)2 catalyst, aryl bromides are efficiently coupled at the C5-position of the imidazole units, which are widely decorated. Under these conditions, only the C-H bond arylation reaction occurred without affecting the integrity of chem. structure of the imidazole-based pharmaceuticals. Moreover, with Bifonazole, Pd-catalyzed C-H bond diarylation at the C2- and C5-positions of imidazole unit has also been performed.2-Bromobenzonitrile(cas: 2042-37-7Synthetic Route of C7H4BrN) was used in this study.

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.Synthetic Route of C7H4BrN

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《Palladium-catalyzed cyanation of aryl halides with in situ generated CN- from ClCF2H and NaNH2》 was published in Organic Chemistry Frontiers in 2020. These research results belong to Yu, Changjiang; Ma, Xingxing; Song, Qiuling. Product Details of 623-00-7 The article mentions the following:

An efficient Pd-catalyzed cyanation of aryl halides with in situ generated CN- anions is described. The CN- source stems from the quadruple cleavage of chlorodifluoromethane (ClCF2H) with sodium amide (NaNH2). This transformation features no requirement of a toxic CN source and avoids the problem of HCN generation associated with traditional methods. A series of aryl nitriles are obtained from aryl halides in good yields under mild reaction conditions. After reading the article, we found that the author used 4-Bromobenzonitrile(cas: 623-00-7Product Details of 623-00-7)

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,Product Details 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.

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Nitrile – Wikipedia,
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