Month: October 2022

In 2017,Szilvasi, Tibor; Roling, Luke T.; Yu, Huaizhe; Rai, Prabin; Choi, Sangwook; Twieg, Robert J.; Mavrikakis, Manos; Abbott, Nicholas L. published 《Design of Chemoresponsive Liquid Crystals through Integration of Computational Chemistry and Experimental Studies》.Chemistry of Materials published the findings.Recommanded Product: 105942-08-3 The information in the text is summarized as follows:

We report the use of computational chem. methods to design a chem. responsive liquid crystal (LC). Specifically, we used electronic structure calculations to model the binding of nitrile-containing mesogens (4′-n-pentyl-4-biphenylcarbonitrile) to metal perchlorate salts (with explicit description of the perchlorate anion), which we call the coordinately saturated anion model (CSAM). The model results were validated against exptl. data. We then used CSAM to predict that selective fluorination can reduce the strength of binding of nitrile-containing nematic LCs to metal salt-decorated surfaces and thus generate a faster reordering of LC in response to competitive binding of dimethylmethylphosphonate (DMMP). We tested this prediction via synthesis of fluorinated compounds 3-fluoro-4′-pentyl[1,1′-biphenyl]-4-carbonitrile and 4-fluoro-4′-pentyl-1,1′-biphenyl, and subsequent exptl. measurements of the orientational response of LCs containing these compounds to DMMP. These exptl. measurements confirmed the theor. predictions, thus providing the first demonstration of a chemoresponsive LC system designed from computational chem. The experimental part of the paper was very detailed, including the reaction process of 4-Bromo-2-fluorobenzonitrile(cas: 105942-08-3Recommanded Product: 105942-08-3)

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: 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

In 2019,Inorganica Chimica Acta included an article by Chang, Chao-Wan; Lee, Gene-Hsiang. Reference of 4-Cyanobenzyl bromide. The article was titled 《Synthesis of ruthenium triazolato complexes by the [3 + 2] cycloaddition of a ruthenium azido complex with acetylacetylenes》. The information in the text is summarized as follows:

The [3 + 2] cycloaddition of two acetylacetylenes with ruthenium azido complex [Ru]-N3 (1, [Ru] = (η5-C5H5)(dppe)Ru, dppe = Ph2PCH2CH2PPh2) is reported. The metal-bound heterocyclic complexes produced are triazolato complexes [Ru]N3C2H(COCH3) (2) and [Ru]N3C2(Ph)(COCH3) (3) from 3-butyn-2-one and 4-phenyl-3-butyn-2-one, resp. Both of the structures of 2 and 3 are clearly established as N(2)-bound. Alkylation of 2 with organic halides affords a series of N(1)-bound N(3)-alkyl-4-acetyl triazolato complexes {[Ru]N3(CH2R)C2H(COCH3)}[X] (4a, R = H, X = I; 4b, R = C6F5, X = Br; 4c, R = Ph, X = Br; 4d, R = 2,6-F2-C6H3, X = Br; 4e, R = 4-CN-C6H4, X = Br). Treatment of 4a with CH3I in refluxing CHCl3 afforded [Ru]-I (5). The structures of complexes 2, 3, 4a and 5 have been determined by single-crystal x-ray diffraction anal. The results came from multiple reactions, including the reaction of 4-Cyanobenzyl bromide(cas: 17201-43-3Reference of 4-Cyanobenzyl bromide)

4-Cyanobenzyl bromide(cas: 17201-43-3) is a white solid. Its melting point is 113-117°C, and flash point is 125.1°C. It is insoluble in water at 20°C. It is stable under normal temperatures and pressures. It should be stored at 0-5°C.Reference of 4-Cyanobenzyl bromide

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Visible light driven, nickel-catalyzed aryl esterification using a triplet photosensitiser thioxanthen-9-one》 were Zhu, Da-Liang; Li, Hong-Xi; Xu, Ze-Ming; Li, Hai-Yan; Young, David J.; Lang, Jian-Ping. And the article was published in Organic Chemistry Frontiers in 2019. Application In Synthesis of 4-Bromobenzonitrile The author mentioned the following in the article:

An approach to the visible light-initiated, nickel-catalyzed esterification of carboxylic acids RC(O)OH (R = Me, Ph, 2H-1,3-benzodioxol-5-yl, adamantan-1-yl, etc.) with aryl bromides ArBr (Ar = Ph, 3-cyano-4-fluorophenyl, 6-(trifluoromethyl)pyridin-2-yl, etc) have been reported. Thioxanthen-9-one works as a triplet photosensitizer to significantly accelerate this cross-coupling to provide aryl esters ArOC(O)R in moderate to excellent yields at room temperature A mechanistic investigation indicates that this esterification undergoes the stepwise oxidative addition of an 4-bromobenzonitrile to nickel, transmetalation of an aryl-Ni(II) bromide complex I, energy transfer from thioxanthen-9-one to an excited-state aryl-Ni(II) carboxylate and reductive elimination to the 4-cyanophenyl acetate. This study contributes to the utilization of ketones as triplet photosensitizers in photochem. transformations. The results came from multiple reactions, including the reaction of 4-Bromobenzonitrile(cas: 623-00-7Application In Synthesis of 4-Bromobenzonitrile)

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,Application In Synthesis of 4-Bromobenzonitrile 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 《Halogen Atom and Position Dependent Strong Enhancement of Solid-State Fluorescence and Stimuli Responsive Reversible Fluorescence Switching》 were Gayathri, Parthasarathy; Karthikeyan, Subramanian; Moon, Dohyun; Anthony, Savarimuthu Philip. And the article was published in ChemistrySelect in 2019. Synthetic Route of C8H6BrN The author mentioned the following in the article:

Halogen (F, Cl and Br) substituted triphenylamine (TPA)-phenylacetonitrile donor-acceptor aggregation enhanced emissive (AEE) compounds have been synthesized and investigated halogen atom and substitution position dependent solid-state fluorescence. Interestingly, para position substituted compounds exhibited stronger fluorescence compared to meta position substituted compounds Further, strong enhancement of fluorescence efficiency was observed with increase of at. size from H to Br (Φf=11.81 to 33.05%). Solid state structural studies revealed formation of halogen-H and halogen-π interactions in the crystal lattice that rigidified the fluorophores and enhanced the fluorescence. Computational studies have been performed to get insight on the fluorescence efficiency modulation by halogen. Integration of propeller shaped TPA lead to external stimuli induced reversible/self-reversible fluorescence switching. PXRD studies confirmed self-recovering of crystalline state after crushing. Fluorescent PMMA polymer thin films of halogen derivatives showed off-on fluorescence switching upon exposure of acid and base/heating. Thus, the present studies indicate that halogen could be employed for strongly enhancing fluorescence efficiency of organic compounds that might be of potential interest for optoelectronic device application. In the part of experimental materials, we found many familiar compounds, such as 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Synthetic Route of C8H6BrN)

2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione or a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands.Synthetic Route of C8H6BrN

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The author of 《Magnetic MCM-41 nanoparticles as a support for the immobilization of a palladium organometallic catalyst and its application in C-C coupling reactions》 were Tahmasbi, Bahman; Ghorbani-Choghamarani, Arash. And the article was published in New Journal of Chemistry in 2019. Application of 623-00-7 The author mentioned the following in the article:

In this study, the surface of magnetic MCM-41 nanoparticles (MCM-41/Fe3O4) was modified by 3-aminopropyltriethoxysilane (APTES) and further, 1-methylimidazole was anchored on their surface using cyanuric chloride as a linker. Then, Pd2+ ions were immobilized on the surface of the modified MCM-41/Fe3O4 (Pd-imi-CC@MCM-41/Fe3O4), and its application was studied as a magnetically recyclable nanocatalyst in carbon-carbon coupling reactions between a wide range of aryl halides and Bu acrylate, Me acrylate, acrylonitrile, phenylboronic acid, or 3,4-difluorophenylboronic acid under the conditions of a phosphine-free ligand and an air atm. This catalyst has the advantages of both the Fe3O4 nanoparticles and mesoporous MCM-41. The structure of the catalyst was characterized via TEM, SEM, EDS, WDX, N2 adsorption-desorption isotherm, XRD, TGA, FT-IR, and AAS. Also, the recovered catalyst was characterized via SEM, AAS and FT-IR. All the products from the carbon-carbon coupling reaction were obtained with excellent yields and high TON and TOF values, which indicate the high efficiency and activity of this catalyst. The selectivity of this catalyst was studied with various aryl halides bearing different functional groups. Furthermore, the heterogeneity and stability of Pd-imi-CC@MCM-41/Fe3O4 was studied via AAS, and leaching and poisoning tests. According to the results, this heterogeneous catalyst can be reused several times. In the experiment, the researchers used many compounds, for example, 4-Bromobenzonitrile(cas: 623-00-7Application of 623-00-7)

4-Bromobenzonitrile(cas: 623-00-7) has been used in the synthesis of 4-iodobenzonitrile via photo-induced aromatic Finkelstein iodination reaction.Application 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.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Nucleophilic Acylation with Aromatic Aldehydes to 2 Bromoacetonitrile: An Umpolung Strategy for the Synthesis of Active Methylene Compounds》 was published in Current Organic Synthesis in 2020. These research results belong to Singh, Shailesh; Tiwari, Jyoti; Jaiswal, Deepali; Sharma, Amit Kumar; Singh, Jaya; Singh, Vandana; Singh, Jagdamba. Related Products of 614-16-4 The article mentions the following:

A novel one-pot N-heterocyclic carbene (NHC)-catalyzed acylation of 2-bromoacetonitrile with aromatic aldehydes ArCHO (Ar = Ph, 2-chlorophenyl, furan-2-yl, etc.) is reported. The protocol involves carbonyl umpolung reactivity of aldehydes in which the carbonyl carbon attacks nucleophilically (as d1 nucleophile) on the electrophilic terminal of 2-bromoacetonitrile to afford 3-aryl-3-oxopropanenitriles ArC(O)CH2CN. The salient features of this procedure are short reaction time, operational simplicity, ambient temperature, no byproduct formation and high yields. After reading the article, we found that the author used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Related Products of 614-16-4)

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.Related Products of 614-16-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《Identification of a potent heme oxygenase-2 (HO-2) inhibitor by targeting the secondary hydrophobic pocket of the HO-2 western region》 was published in Bioorganic Chemistry in 2020. These research results belong to Floresta, Giuseppe; Fallica, Antonino N.; Romeo, Giuseppe; Sorrenti, Valeria; Salerno, Loredana; Rescifina, Antonio; Pittala, Valeria. HPLC of Formula: 17201-43-3 The article mentions the following:

The enzymic family of heme oxygenase (HO) is accountable for heme breakdown. Among the two isoforms characterized to date, HO-2 is poorly investigated due to the lack of potent HO-2 chem. modulators and the greater attentiveness towards HO-1 isoform. In the present paper, we report the rational design and synthesis of HO-2 inhibitors achieved by modulating the volume of known HO-1 inhibitors. The inhibition preference has been moved from HO-1 to HO-2 by merely increasing the volume of the substituent in the western region of the inhibitors. Docking studies demonstrated that new derivatives soak differently in the two binding pockets, probably due to the presence of a Tyr187 residue in HO-2. These findings could be useful for the design of new selective HO-2 compounds The experimental process involved the reaction of 4-Cyanobenzyl bromide(cas: 17201-43-3HPLC of Formula: 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.HPLC of Formula: 17201-43-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

《One-pot synthesis of bio-supported Pd nanoparticles by using clove leaf and their catalytic performance for Suzuki coupling reaction》 was published in Journal of Molecular Structure in 2020. These research results belong to Wang, Zhen; Bai, Xuefeng. Electric Literature of C7H4BrN The article mentions the following:

Bio-supported palladium nanoparticles (PdNPs/RCL-b) were synthesized by one-pot method without adding any chem. reducing and stabilizing agents. In the preparation process, Clove leaf (CL) was used as carrier, reducing and stabilizing agents. The extraction of reducing compounds from CL, the reduction and stabilization of Pd2+, and palladium nanoparticles (PdNPs) loading on the extraction residue of CL (RCL) were accomplished simultaneously, avoiding the agglomeration of PdNPs and ensuring PdNPs loading evenly on RCL. The prepared PdNPs/RCL-b catalysts were characterized by XRD, UV-Vis, Micro-IR spectroscopy, FT-IR and TEM. The hydroxyl groups and other reductive groups which exist in polyphenols and flavonoids reduced Pd2+ to PdNPs, while the C=O, C-O and other groups containing O served as good protective agents and stabilizers for the formation of PdNPs. The PdNPs had a face-centered cubic structure with a particle size distribution of 1.26-8.78 nm and an average particle size of 4.49 nm, and uniformly dispersed on the surface of RCL. The results of catalytic Suzuki coupling reaction between 4-bromonitrobenzene and phenylboronic acid over PdNPs/RCL-b at 60°C showed that the yield was 96.22% for 20 min and the value of TOF was 5773.2 h-1. After the reaction between 4-bromotoluene and phenylboronic acid repeated for 8 times, the yield remains above 91%. This method provides a more facile, efficient and green approach to the preparation of supported nano-palladium catalysts. After reading the article, we found that the author used 4-Bromobenzonitrile(cas: 623-00-7Electric Literature of 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,Electric Literature of 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

Liu, Hui; Yan, Yingkun; Li, Min; Zhang, Xiaomei published an article in 2021. The article was titled 《An enantioselective aza-Friedel-Crafts reaction of 5-aminoisoxazoles with isatin-derived N-Boc ketimines》, and you may find the article in Organic & Biomolecular Chemistry.Electric Literature of C9H7NO The information in the text is summarized as follows:

By employing a chiral phosphoric acid as a catalyst, an enantioselective aza-Friedel-Crafts reaction of 5-aminoisoxazoles with isatin-derived N-Boc ketimines was realized. The reaction provided a wide variety of novel 3-isoxazole 3-amino-oxindoles I (R1 = C6H5, 4-OMeC6H4, 4-FC6H4, etc.; R2 = Me, Et, Bn, Allyl; R3 = H, 5-Me, 5-Cl, etc.; R4 = H, Me, Et, Bn, Boc) with good yields (up to 99%) and moderate to good enantioselectivities (up to 99%). The absolute configuration of one product was assigned by X-ray crystal structural anal. and a plausible reaction mechanism was proposed. In addition, a scale-up reaction was performed successfully. Finally, one product was subjected to Suzuki-Miyaura coupling with phenylboronic acid to afford the product in a moderate yield without erosion of the enantioselectivity. The experimental process involved the reaction of 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Electric Literature of C9H7NO)

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.Electric Literature of C9H7NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

In 2022,Lai, Nang Duy; Nguyen, Thu Trang; Nguyen, Nhu Ngan Ha; Retailleau, Pascal; Mac, Dinh Hung; Nguyen, Thanh Binh published an article in Organic Chemistry Frontiers. The title of the article was 《Direct access to 2-aryl-3-cyanothiophenes by a base-catalyzed one-pot two-step three-component reaction of chalcones with benzoylacetonitriles and elemental sulfur》.Quality Control of 3-Oxo-3-phenylpropanenitrile The author mentioned the following in the article:

Herein, unexpected results on the formation of 3-cyanothiophene derivatives as the major products via a three-component reaction of chalcones, benzoylacetonitriles and elemental sulfur along with the minor products 2-aminothiophenes was reported. The ratios between these two thiophene products is 4 : 3 and could be varied by simply changing the promoting base as well as its stoichiometric ratio. The method was successfully extended to benzoylacetate in place of benzoylacetonitrile to provide thiophene-3-carboxylates. In the experimental materials used by the author, we found 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Quality Control of 3-Oxo-3-phenylpropanenitrile)

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.Quality Control of 3-Oxo-3-phenylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts