Category: ethers-buliding-blocks

2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide as a novel ligand for the copper-catalyzed coupling reaction of phenols and aryl halides was written by Qiu, Yatao;Jia, Weijun;Yao, Zhiyi;Wu, Fanhong;Jiang, Sheng. And the article was included in Organic & Biomolecular Chemistry in 2013.Electric Literature of C15H14O3 This article mentions the following:

2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide was identified as an efficient novel ligand for the copper-catalyzed coupling of aryl halides with various phenols under mild conditions. The catalytic system shows great functional-group tolerance and excellent reactive selectivity. In the experiment, the researchers used many compounds, for example, 1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8Electric Literature of C15H14O3).

1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8) 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. 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.Electric Literature of C15H14O3

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

Carboxylic Acid-Catalyzed Highly Efficient and Selective Hydroboration of Alkynes with Pinacolborane was written by Ho, Hon Eong;Asao, Naoki;Yamamoto, Yoshinori;Jin, Tienan. And the article was included in Organic Letters in 2014.Electric Literature of C6H10O2 This article mentions the following:

We have demonstrated for the first time that carboxylic acids are able to catalyze the direct hydroboration of various terminal and internal alkynes with pinacolborane, HB(pin), without using any metal catalysts. For example, PhCCB(pin) reacts with HB(pin) in the presence of 4-Me₂NC₆H₄CO₂H giving PhCH:C[B(pin)]₂ in 99% yield. This unprecedented catalytic hydroboration exhibits a broad functional groups compatibility, giving the corresponding alkenyl diboronates and monoboronates in good to high yields with exclusive regio- and stereoselectivities. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Electric Literature of C6H10O2).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) 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 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.Electric Literature of C6H10O2

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

Synthesis of tris-(azacrown) ethers for carboxylic acid recognition was written by Lee, Michael;Zali-Boeini, Hassan;Li, Feng;Lindoy, Leonard F.;Jolliffe, Katrina A.. And the article was included in Tetrahedron in 2013.Formula: C10H21NO4 This article mentions the following:

The synergistic enhancement of metal ion extraction by azacrown ethers in the presence of carboxylic acids has been attributed to a ligand assembly effect in which these two ligands form a complex, facilitated by proton transfer, prior to complexation of the metal ion. In order to investigate the first steps in this multi-component complexation procedure, six tris-(azacrown) ethers I [n = 1, 2; R = H, Me, Et] were synthesized in high yields and their ability to complex mono- and tri-carboxylic acids was investigated by ¹H NMR in methanol-d₄. All six compounds bound to benzoic acid with 1:3 host-guest stoichiometry and four of them bound tricarboxylic acids with 1:1 host-guest stoichiometry, providing good support for the proposed first step in the ligand assembly effect. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Formula: C10H21NO4).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) 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).Formula: C10H21NO4

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

Control of peroxyoxalate chemiluminescence by nitrogen-containing ligand quenching: turning off and on by ligand-metal ion host-guest interactions was written by Maruyama, Takayuki;Fujie, Yasuyuki;Oya, Noriyuki;Hosaka, Eisuke;Kanazawa, Aki;Tanaka, Daisuke;Hattori, Yoshiyuki;Motoyoshiya, Jiro. And the article was included in Tetrahedron in 2011.Quality Control of 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

The control of peroxyoxalate chemiluminescence (PO-CL) by the coordination of nitrogen-containing ligands and metal cations was investigated. Turning the CL off and on was done by PO-CL using 15-monoazacrown-5-tethered anthracene and alkali metal ions. CL quenching and regeneration was also observed in the separated mol. system of 15-monoazacrown-5 and the fluorophores. CL quenching by a number of ligands bearing dipicolylamino groups was evaluated by these PO-CL reactions and found to be closely related to their oxidation potentials, which is dependent on the Weller rate law for electron exchange and this provides strong support for the existence of the CIEEL PO-CL process. When Zn²⁺ or Cu²⁺ are added to the PO-CL system quenched by the ligand, N-[2-(2,2′-dipicolylamino)ethyl]aniline, CL was turned on because the electron donating ability of the ligands was modulated. This was controlled by the coordination of the studied metal ions and, therefore, this system results in CL because of host-guest interactions. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Quality Control of 1,4,7,10-Tetraoxa-13-azacyclopentadecane).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) 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. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Quality Control of 1,4,7,10-Tetraoxa-13-azacyclopentadecane

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

Influence of Porosity of Sulfide-Based Artificial Solid Electrolyte Interphases on Their Performance with Liquid and Solid Electrolytes in Li and Na Metal Batteries was written by Lim, Kyungmi;Fenk, Bernhard;Kuester, Kathrin;Acartuerk, Tolga;Weiss, Juergen;Starke, Ulrich;Popovic, Jelena;Maier, Joachim. And the article was included in ACS Applied Materials & Interfaces in 2022.SDS of cas: 112-49-2 This article mentions the following:

Realization of all-solid-state batteries combined with metallic Li/Na is still hindered due to the unstable interface between the alkali metal and solid electrolytes, especially for highly promising thiophosphate materials. Artificial and uniform solid-electrolyte interphases (SEIs), serving as thin ion-conducting films, have been considered as a strategy to overcome the issues of such reactive interfaces. Here, we synthesized sulfide-based artificial SEIs (Li_xS_y and Na_xS_y) on Li and Na by solid/gas reaction between the alkali metal and S vapor. The synthesized films are carefully characterized with various chem./electrochem. techniques. We show that these artificial SEIs are not beneficial from an application point of view since they either contribute to addnl. resistances (Li) or do not prevent reactions at the alkali metal/electrolyte interface (Na). We show that Na_xS_y is more porous than Li_xS_y, supported by (i) its rough morphol. observed by focused ion beam-SEM, (ii) the rapid decrease of R_interface (interfacial resistance) in Na_xS_y-covered-Na sym. cells with liquid electrolyte upon aging under open-circuit potential, and (iii) the increase of R_interface in Na_xS_y-covered-Na solid-state sym. cells with Na₃PS₄ electrolyte. The porous SEI allows the penetration of liquid electrolyte or alkali metal creep through its pores, resulting in a continuous chem. reaction. Hence, porosity of SEIs in general should be carefully taken into account in the application of batteries containing both liquid electrolyte and solid electrolyte. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2SDS of cas: 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. 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.SDS of cas: 112-49-2

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

Highly dispersed palladium nanoparticles supported on an imidazolium-based ionic liquid polymer: an efficient catalyst for oxidation of alcohols was written by Karimi, Z.;Hassanpour, A.;Kangari, S.;Marjani, A.. And the article was included in Russian Chemical Bulletin in 2022.Recommanded Product: 105-13-5 This article mentions the following:

An efficient and stable nanocatalyst for selective oxidation of alcs. was developed. It contains palladium nanoparticles, which are well distributed throughout the network of a copolymer based on an ionic liquid The synthesized nanomaterials were characterized by various techniques such as nitrogen adsorption-desorption anal., thermal gravimetric anal., TEM, and FTIR spectroscopy. A high surface area and the appropriate pore size of the nanocatalyst make active metal sites accessible to reagents, whereas the presence of an ionic liquid in the network of the polymer structure creates a good environment for the leaching protection and stabilization of extremely dispersed palladium nanoparticles. The availability and abundance of active sites of highly dispersed palladium nanoparticles make the synthesized nanocatalyst very promising for oxidation of alcs. The nanocatalyst has a number of features such as a high surface area, an appropriate size of pores with high catalytic activity, high thermal stability of the nanostructures, and low amounts of the ionic liquid needed for its synthesis. Using this nanocatalyst, carbonyl compounds were prepared from the corresponding alcs. in high yields. Addnl., the prepared nanocatalyst can easily be recovered by centrifugation after completion of the reactions and was reused five times without a significant loss in its catalytic activity. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Recommanded Product: 105-13-5).

(4-Methoxyphenyl)methanol (cas: 105-13-5) 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. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Recommanded Product: 105-13-5

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

Multiple Hydrogen Bond Channel Structural Electrolyte for an Enhanced Carbon Fiber Composite Battery was written by Choi, Jaehoon;Zabihi, Omid;Varley, Russell;Zhang, Jane;Fox, Bronwyn L.;Naebe, Minoo. And the article was included in ACS Applied Energy Materials in 2022.COA of Formula: C8H18O4 This article mentions the following:

Structural batteries made of carbon fiber composites have been receiving great attention for automotive application in the last decade. However, a structural battery electrolyte (SBE) for the structural batteries is conventionally dependent on utilizing highly volatile carbonate-derivative liquid electrolytes to provide moderate ionic conduction. This study introduces a SBE which fabricates as a two-phase system via reaction-induced phase transition as well as includes a hybridized electrolyte, consisting of a low flammability electrolyte with a solid additive-inducing multihydrogen bond. The proposed SBE is composed of a vinyl ester polymer containing triethylene glycol di-Me ether (TriG) and cyclohexanedimethanol (CHDM) as a quasi-solid additive. Confirmed by Fourier transform IR, Raman, and ⁷Li-NMR results, the contents of CHDM in the SBE structure play a crucial role not only through the plasticizing effect but also through the formation of a multidimension channel via a hydrogen bond, thereby contributing to enhancing the motion of the cation in the SBE. The optimized SBE (Li-TriG-CHDM10) shows an ionic conductivity of 2.0 x 10^-4 S cm^-1 with an E’ of ~300 MPa at ambient temperature To exhibit the possibility for a structural battery, the carbon fiber composite lamina was fabricated using an optimized SBE and evaluated as a battery half-cell, showing the potential of a high bearing mech. load and ion transport between the carbon fibers and the electrolytes. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2COA of Formula: C8H18O4).

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. But on the other hand, ethers undergo cleavage by reaction with acids. 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.COA of Formula: C8H18O4

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

Mesomorphic substances. III. Nematic tolans was written by Malthete, Jacques;Leclercq, Martine;Dvolaitzky, Maya;Gabard, Jacqueline;Billard, Jean;Pontikis, Vassilis;Jacques, Jean. And the article was included in Molecular Crystals and Liquid Crystals in 1973.Quality Control of 1-Methoxy-4-((4-propylphenyl)ethynyl)benzene This article mentions the following:

p,p’-Disubstituted diphenylacetylenes p-ROC6H4CCC6H4R’p are prepared Sym. and nonsym. diethers (R’ = OR and R’ = OR”) and p’-alkylated monoethers are described. Most of these compounds are nematic at temperatures <50%. The temperatures and heats of transition and electrooptical characteristics (εâŠ?and εâ€? of the compounds are given. The preparation of mesomorphic mixtures at room temperature is discussed. In the experiment, the researchers used many compounds, for example, 1-Methoxy-4-((4-propylphenyl)ethynyl)benzene (cas: 39969-26-1Quality Control of 1-Methoxy-4-((4-propylphenyl)ethynyl)benzene).

1-Methoxy-4-((4-propylphenyl)ethynyl)benzene (cas: 39969-26-1) 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. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Quality Control of 1-Methoxy-4-((4-propylphenyl)ethynyl)benzene

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

An O-Benzyl Phosphonamidate Prodrug of Tenofovir for the Treatment of Hepatitis B Virus Infection was written by Zhang, Qianqian;Peng, Youmei;Hou, Jiao;Chen, Yanhong;Liu, Bingjie;Zhang, Pinghu;Yu, Wenquan;Chang, Junbiao. And the article was included in Journal of Medicinal Chemistry in 2022.Quality Control of (4-Methoxyphenyl)methanol This article mentions the following:

A series of new O-(substituted benzyl) phosphoramidate prodrugs of tenofovir for the treatment of hepatitis B virus (HBV) infections have been designed and synthesized. An investigation of structure-activity relationships revealed that the compound bearing an o-methylbenzyl group (1a) has the most potent in vitro anti-HBV activity. This prodrug (1a) was well-tolerated in KM mice via intragastric administration at a dosage of up to 1.5 g/kg. In DHBV-infected ducks, prodrug 1a displayed a good inhibitory effect on the viral DNA replication in both the serum and the liver in a time- and dose-dependent manner and did not cause any necrosis, hemorrhage, or inflammatory response in the animal livers. Further investigation demonstrated that prodrug 1a achieved a higher exposure of the bioactive metabolite (tenofovir diphosphate, TFV-DP) in the liver, the target organ for the treatment of HBV infection, than tenofovir alafenamide fumarate (TAF) did at an equimolar dose. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Quality Control of (4-Methoxyphenyl)methanol).

(4-Methoxyphenyl)methanol (cas: 105-13-5) 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. 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.Quality Control of (4-Methoxyphenyl)methanol

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

Palladium-catalyzed aryl amination- heck cyclization cascade: a one-flask approach to 3-substituted indoles was written by Jensen, Thomas;Pedersen, Henrik;Bang-Andersen, Benny;Madsen, Robert;Joergensen, Morten. And the article was included in Angewandte Chemie, International Edition in 2008.HPLC of Formula: 56619-93-3 This article mentions the following:

A Pd/dppf-based catalyst provides access to the title compounds from 1,2-dihalogenated aromatic compounds and allylic amines in a single reaction flask. The initial aryl amination step occurs with excellent selectivity for the aryl iodide to ensure the formation of a single indole regioisomer, which can be functionalized in situ by N-arylation. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3HPLC of Formula: 56619-93-3).

N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) 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 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.HPLC of Formula: 56619-93-3

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