Month: January 2023

Redox-Divergent Construction of (Dihydro)thiophenes with DMSO was written by Liu, Heng;He, Gu-Cheng;Zhao, Chao-Yang;Zhang, Xiang-Xin;Ji, Ding-Wei;Hu, Yan-Cheng;Chen, Qing-An. And the article was included in Angewandte Chemie, International Edition in 2021.Formula: C14H21BO4 This article mentions the following:

Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing mols. Inspired by the redox diversity of these features in nature, herein a redox-divergent construction of dihydrothiophenes, thiophenes, and bromothiophenes from the resp. readily available allylic alcs., DMSO (DMSO), and HBr is reported. The redox-divergent selectivity could be manipulated mainly by controlling the dosage of DMSO and HBr. Mechanistic studies suggest that DMSO simultaneously acts as an oxidant and a sulfur donor. The synthetic potentials of the products as platform mols. were also demonstrated by various derivatizations, including the preparation of bioactive and functional mols. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4Formula: C14H21BO4).

2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4) belongs to ethers. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Formula: C14H21BO4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Convenient and flexible syntheses of gem-dimethyl carboxylic triggers via mono-selective β-C(sp³)-H arylation of pivalic acid with ortho-substituted aryl iodides was written by Huang, Yongliang;Du, Yu;Su, Weiping. And the article was included in Organic Chemistry Frontiers in 2022.Safety of 4-Iodo-1-methoxy-2-methylbenzene This article mentions the following:

This work presents a palladium(II)-catalyzed mono-selective C(sp³)-H arylation of pivalic acid for rapid construction of an important library of 3-aryl-2,2-dimethylpropanoic acids, especially ortho-substituted-aryl compounds The strategy greatly streamlines access to a series of trimethyl-lock-type triggers – arylated gem-di-Me carboxylic acids bearing ortho-activatable substituents, which was used as a self-immolative spacer for selective chem. release initiated under specific conditions. Flexible transformation and derivatization of these activatable carboxylic triggers were also showcased. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2Safety of 4-Iodo-1-methoxy-2-methylbenzene).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Safety of 4-Iodo-1-methoxy-2-methylbenzene

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Lithium-Metal Batteries Using Sustainable Electrolyte Media and Various Cathode Chemistries was written by Marangon, Vittorio;Minnetti, Luca;Adami, Matteo;Barlini, Alberto;Hassoun, Jusef. And the article was included in Energy & Fuels in 2021.HPLC of Formula: 112-49-2 This article mentions the following:

Lithium-metal batteries employing concentrated glyme-based electrolytes and two different cathode chemistries are herein evaluated in view of a safe use of the highly energetic alkali-metal anode. Indeed, diethylene-glycol dimethyl-ether (DEGDME) and triethylene-glycol dimethyl-ether (TREGDME) dissolving lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) and lithium nitrate (LiNO₃) in concentration approaching the solvents saturation limit are used in lithium batteries employing either a conversion sulfur-tin composite (S:Sn 80:20 weight/weight) or a Li⁺ (de)insertion LiFePO₄ cathode. Cyclic voltammetry (CV) and electrochem. impedance spectroscopy (EIS) clearly show the suitability of the concentrated electrolytes in terms of process reversibility and low interphase resistance, particularly upon a favorable activation. Galvanostatic measurements performed on lithium-sulfur (Li/S) batteries reveal promising capacities at room temperature (25°C) and a value as high as 1300 mAh g_S^-1 for the cell exploiting the DEGDME-based electrolyte at 35°C. On the other hand, the lithium-LiFePO₄ (Li/LFP) cells exhibit satisfactory cycling behavior, in particular when employing an addnl. reduction step at low voltage cutoff (i.e., 1.2 V) during the first discharge to consolidate the solid electrolyte interphase (SEI). This procedure allows a Coulombic efficiency near 100%, a capacity approaching 160 mAh g^-1, and relevant retention particularly for the cell using the TREGDME-based electrolyte. Therefore, this work suggests the use of concentrated glyme-based electrolytes, the fine-tuning of the operative conditions, and the careful selection of active materials chem. as significant steps to achieve practical and safe lithium-metal batteries. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2HPLC of Formula: 112-49-2).

2,5,8,11-Tetraoxadodecane (cas: 112-49-2) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).HPLC of Formula: 112-49-2

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Nitro derivatives of N-alkylbenzoaza-15-crown-5: synthesis, structures, and complexation with metal and ammonium cations was written by Dmitrieva, S. N.;Churakova, M. V.;Kurchavov, N. A.;Vedernikov, A. I.;Kuz’mina, L. G.;Freidzon, A. Ya.;Bagatur’yants, A. A.;Strelenko, Yu. A.;Howard, J. A. K.;Gromov, S. P.. And the article was included in Russian Chemical Bulletin in 2010.Application In Synthesis of 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

A number of N-alkylnitrobenzoaza-15-crown-5 with the macrocycle N atom conjugated with the benzene ring were obtained. The structural and complexing properties of these compounds were compared with those of model nitrobenzo- and N-(4-nitrophenyl)aza-15-crown-5 using X-ray diffraction, ¹H NMR spectroscopy, and DFT calculations The macrocyclic N atom of benzoazacrown ethers are characterized by a considerable contribution of the sp³-hybridized state and a pronounced pyramidal geometry; the crownlike conformation of the macrocycle is preorganized for cation binding, which facilitates complexation. The stability constants of the complexes of crown ethers with the NH₄⁺, EtNH₃⁺, Na⁺, K⁺, Ca²⁺, and Ba²⁺ ions were determined by ¹H NMR titration in MeCN-d₃. The most stable complexes were obtained with alk.-earth metal cations, which is due to the higher charge d. at these cations. The characteristics of the complexing ability of N-alkylnitrobenzoaza-15-crown-5 toward alk. earth metal cations are comparable with analogous characteristics of nitrobenzo-15-crown-5 and are much better than those of N-(4-nitrophenyl)aza-15-crown-5. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Application In Synthesis of 1,4,7,10-Tetraoxa-13-azacyclopentadecane).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.Application In Synthesis of 1,4,7,10-Tetraoxa-13-azacyclopentadecane

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Investigation of the relationship between the inhibitory activity of glycolic acid oxidase (GAO) and its chemical structure: electron-topological approach was written by Guzel, Y.. And the article was included in Journal of Molecular Structure: THEOCHEM in 1996.Synthetic Route of C9H10O4 This article mentions the following:

Rules for the occurrence of the inhibitory activity of glycolic acid oxidase are formulated and discussed in terms of the so-called electron-topol. approach. It is shown that the mol. fragment responsible for this kind of activity possesses fixed electronic and geometrical characteristics caused by a definite spatial arrangement of an oxygen atom and a group of carbon atoms. A series of 85 compounds including 36 active and 49 inactive compounds was studied. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Synthetic Route of C9H10O4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Synthetic Route of C9H10O4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Cucurbit[n]urils (n = 7, 8) can strongly bind neutral hydrophilic molecules in water was written by Li, Ming-Shuang;Quan, Mao;Yang, Xi-Ran;Jiang, Wei. And the article was included in Science China: Chemistry in 2022.Synthetic Route of C8H18O4 This article mentions the following:

It is challenging to recognize neutral hydrophilic mols. in water. Effective use of hydrogen bonds in water is generally accepted to be the key to success. In contrast, hydrophobic cavity is usually considered to play an insignificant role or only to provide a nonpolar microenvironment for hydrogen bonds. Herein, we report that hydrophobic cavity alone can also strongly bind neutral, highly hydrophilic mols. in water. We found that cucurbit[n]urils (n = 7, 8) bind 1,4-dioxane, crown ethers and monosaccharides in water with remarkable affinities. The best binding constant reaches 10⁷ M^-1 for cucurbit[8]uril, which is higher than its binding affinities to common organic cations. D. functional theory (DFT) calculations and control experiments reveal that the hydrophobic effect is the major contributor to the binding through releasing the cavity water and/or properly occupying the weakly hydrated cavity. However, hydrophobic cavity still prefers nonpolar guests over polar guests with similar size and shape. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2Synthetic Route of C8H18O4).

2,5,8,11-Tetraoxadodecane (cas: 112-49-2) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Synthetic Route of C8H18O4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Scope and limitations of the dual-gold-catalysed hydrophenoxylation of alkynes was written by Gomez-Suarez, Adrian;Oonishi, Yoshihiro;Martin, Anthony R.;Nolan, Steven P.. And the article was included in Beilstein Journal of Organic Chemistry in 2016.Application In Synthesis of 1,4-Dimethoxy-2-butyne This article mentions the following:

Due to the synthetic advantages presented by the dual-gold-catalyzed hydrophenoxylation of alkynes RCCR¹ (R = Et, Ph, 2-thienyl, etc.; R¹ = H, Ph, 2-thienyl, naphth-1-yl, etc.), a thorough study of this reaction was carried out in order to fully define the scope and limitations of the methodol. The protocol tolerates a wide range of functional groups, such as nitriles, ketones, esters, aldehydes, ketals, naphthyls, allyls or polyphenols, in a milder and more efficient manner than the previously reported methodologies. The highly steric hindered phenols XOH (X = 2-naphthyl, 2-HOC₆H₄, 2H-1,3-benzodioxol-5-yl, etc.) can be used has been identified, small changes on the steric bulk of the alkynes have a dramatic effect on the reactivity. More importantly, the use of substrates that facilitate the formation of diaurated species such as gem-diaurated or σ,π- digold-acetylide species, hinder the catalytic activity has been observed Moreover, the use of directing groups in unsym. alkynes can help to achieve high regioselectivity in the hydrophenoxylation has been identified. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Application In Synthesis of 1,4-Dimethoxy-2-butyne).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. But on the other hand, ethers undergo cleavage by reaction with acids. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Application In Synthesis of 1,4-Dimethoxy-2-butyne

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Prediction of acidity constant for substituted acetic acids in water using artificial neural networks was written by Habibi-Yangjeh, Aziz;Danandeh-Jenagharad, Mohammad. And the article was included in Indian Journal of Chemistry in 2007.Category: ethers-buliding-blocks This article mentions the following:

Linear and non-linear quant. structure-activity relationships have been successfully developed for the modeling and prediction of acidity constant (pK_a) of 87 substituted acetic acids with diverse chem. structures. The descriptors appearing in the multi-parameter linear regression (MLR) model are considered as inputs for developing the back-propagation artificial neural network (BP-ANN). ANN model is constructed using two mol. descriptors; the most pos. charge of acidic hydrogen atom (Q⁺) and most neg. charge of the carboxylic oxygen atom (q^–) as inputs and its output is pK_a. It has been found that properly selected and trained neural network with 53 substituted acetic acids could fairly represent dependence of the acidity constant on mol. descriptors. For evaluation of the predictive power of the generated ANN, an optimized network has been applied for prediction pK_a values of 17 compounds in the prediction set. Mean percentage deviation (MPD) for prediction set using the MLR and ANN models are 9.135 and 1.362, resp. These improvements are due to the fact that the pK_a of substituted acetic acids demonstrates non-linear correlations with the mol. descriptors. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Category: ethers-buliding-blocks).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.Category: ethers-buliding-blocks

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

High-Throughput Optimization of Ir-Catalyzed C-H Borylation: A Tutorial for Practical Applications was written by Preshlock, Sean M.;Ghaffari, Behnaz;Maligres, Peter E.;Krska, Shane W.;Maleczka, Robert E.;Smith, Milton R.. And the article was included in Journal of the American Chemical Society in 2013.Product Details of 365564-07-4 This article mentions the following:

With the aid of high-throughput screening, the efficiency of Ir-catalyzed C-H borylations has been assessed as functions of precatalyst, boron reagent, ligand, order of addition, temperature, solvent, and substrate. This study not only validated some accepted practices but also uncovered unconventional conditions that were key to substrate performance. Authors anticipate that insights drawn from these findings will be used to design reaction conditions for substrates whose borylations are difficult to impossible using standard catalytic conditions. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4Product Details of 365564-07-4).

2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. Ethyl ether is an excellent solvent for extractions and for a wide variety of chemical reactions. It is also used as a volatile starting fluid for diesel engines and gasoline engines in cold weather. Dimethyl ether is used as a spray propellant and refrigerant. Methyl t-butyl ether (MTBE) is a gasoline additive that boosts the octane number and reduces the amount of nitrogen-oxide pollutants in the exhaust. The ethers of ethylene glycol are used as solvents and plasticizers.Product Details of 365564-07-4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

2-(4-Methoxyphenoxy)acetohydrazide was written by Liu, Gang;Gao, Jie. And the article was included in Acta Crystallographica, Section E: Structure Reports Online in 2012.Application In Synthesis of 2-(4-Methoxyphenoxy)acetic acid This article mentions the following:

The title compound, C₉H₁₂N₂O₃, was synthesized by the reaction of Et 2-(4-methoxyphenoxy)acetate with hydrazine hydrate in ethanol. In the acetohydrazide group, the N-N bond is relatively short [1.413 (2) Å], suggesting some degree of electronic delocalization in the mol. In the crystal, mols. are linked into sheets lying parallel to the ab plane by N-H···N and N-H···O hydrogen bonds. Crystallog. data are given. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Application In Synthesis of 2-(4-Methoxyphenoxy)acetic acid).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Application In Synthesis of 2-(4-Methoxyphenoxy)acetic acid

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem