Balakrishnan, Venkadesh et al. published their research in Organic Letters in 2022 | CAS: 105-13-5

(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. But on the other hand, ethers undergo cleavage by reaction with acids. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O閳ユ椊 or N閳ユ椊 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.Category: ethers-buliding-blocks

Interception of Nickel Hydride Species and Its Application in Multicomponent Reactions was written by Balakrishnan, Venkadesh;Ganguly, Anirban;Rasappan, Ramesh. And the article was included in Organic Letters in 2022.Category: ethers-buliding-blocks This article mentions the following:

The hydrogen borrowing strategy is an economical method for the 浼?functionalization of ketones. While this strategy is extremely advantageous, it does not lend itself to the synthesis of 灏?灏?disubstituted ketones. This can be achieved, if the in situ generated metal hydride can be intercepted with a nucleophilic coupling partner. Authors present a multicomponent strategy for the coupling of alcs., ketones, and boronic acids using only 1 mol % nickel catalyst and without the need for added ligands. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Category: ethers-buliding-blocks).

(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. But on the other hand, ethers undergo cleavage by reaction with acids. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O閳ユ椊 or N閳ユ椊 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.Category: ethers-buliding-blocks

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

Wang, Donglei et al. published their research in Angewandte Chemie, International Edition in 2022 | CAS: 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. 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.Product Details of 105-13-5

Enantioselective Synthesis of Planar-Chiral Macrocycles through Asymmetric Electrophilic Aromatic Amination was written by Wang, Donglei;Shao, Ying-Bo;Chen, Yunrong;Xue, Xiao-Song;Yang, Xiaoyu. And the article was included in Angewandte Chemie, International Edition in 2022.Product Details of 105-13-5 This article mentions the following:

An efficient approach for asym. synthesis of planar-chiral macrocycles (paracyclophanes) has been disclosed through enantioselective electrophilic aromatic aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. A wide range of chiral macrocycles bearing varied ring sizes (16 to 23-membered) and functional group-containing ansa chains were readily afforded using this method, with excellent yields and high enantioselectivities (23 examples, up to 99.5 : 0.5 er). Exptl. studies and DFT calculations were performed to elucidate the mechanism and origin of stereoselectivities of these reactions. Preliminary utilization of the planar-chiral macrocycle as chiral organocatalyst showcased the potential applications of these novel chiral skeletons. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Product Details of 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. 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.Product Details of 105-13-5

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

de Kruijff, Goswinus H. M. et al. published their research in ChemElectroChem in 2019 | CAS: 1877-75-4

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) 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. 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).Product Details of 1877-75-4

Electrochemical Synthesis of Aryl Methoxymethyl Ethers was written by de Kruijff, Goswinus H. M.;Waldvogel, Siegfried R.. And the article was included in ChemElectroChem in 2019.Product Details of 1877-75-4 This article mentions the following:

Methoxymethyl protected phenols/thiophenols ArXCH2OCH3 [X = O, S; Ar = Ph, 4-ClC6H4, 2,6-di-ClC6H3, etc.] were synthesized by safe, reagent- and reagent waste-free anodic decarboxylation protocol. High current efficiencies and good functional group tolerance made this methodol. a useful tool for the preparation of these valuable and protected phenol building blocks. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Product Details of 1877-75-4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) 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. 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).Product Details of 1877-75-4

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

Al-Awadi, Nouria A. et al. published their research in International Journal of Chemical Kinetics in 2001 | CAS: 1877-75-4

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) 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. 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.Application In Synthesis of 2-(4-Methoxyphenoxy)acetic acid

Kinetics and mechanism of thermal gas-phase elimination of 2-aryloxyacetic acid was written by Al-Awadi, Nouria A.;Kumar, Ajith;Chuchani, Gabriel;Herize, Armando. And the article was included in International Journal of Chemical Kinetics in 2001.Application In Synthesis of 2-(4-Methoxyphenoxy)acetic acid This article mentions the following:

Rates of thermal gas-phase elimination of eleven 2-aryloxyacetic acid have been measured over a 45鎺矯 temperature range for each compound Hammett correlation of the present kinetic data with the literature 锜?sup>0 values of the given substituents gave a reaction 锜?constant of 0.69 at 600 K; this is more than that for the gas-phase elimination parameter of 2-aryloxypropanoic acid (锜?= 0.26) and consistent with a transition state with some charge separation, suggesting a partial formation of carbocation. The implications of this observation for the thermal gas-phase elimination of 浼?aryloxycarboxylic acids are considered. 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. 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. 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.Application In Synthesis of 2-(4-Methoxyphenoxy)acetic acid

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

Thi Bach Tuyet Lam et al. published their research in Phytochemistry in 1992 | CAS: 3929-47-3

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) 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, 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. 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.Related Products of 3929-47-3

Cinnamic acid bridges between cell wall polymers in wheat and phalaris internodes was written by Thi Bach Tuyet Lam;Iiyama, Kenji;Stone, Bruce A.. And the article was included in Phytochemistry in 1992.Related Products of 3929-47-3 This article mentions the following:

A method has been devised for the quant. determination of cinnamic acids participating in ester-ether bridges between cell wall polymers based on the different reactivities of free carboxylic acids and their esters towards borohydride reductants and the different susceptibilities of cinnamic acid ester and benzyl ether linkages to alk. treatments. Lignin-polysaccharide containing fractions extracted with dioxane-H2O from cell walls of wheat (Triticum鑱?em>aestivum) and phalaris (Phalaris鑱?em>aquatica) internodes are hydrogenated using a Pd/C catalyst at room temperature to convert cinnamic acids to their corresponding dihydrocinnamic acids. The sample is subsequently reduced with LiBH4 in ether-toluene to convert ester-linked dihydrocinnamates to their corresponding alcs. and hydrolyzed with 4M NaOH at 170鎺? and the dihydrocinnamic acid derivatives released from their etherified forms were determined by GC. Using model compounds it was shown that these reactions proceeded quant. The results indicate that all of the etherified ferulic acid in the dioxane-H2O-soluble fractions of walls of wheat and phalaris internodes is also ester-linked. It has been calculated that there are nine to 10 ferulic acid ester-ether bridges for every 100 C6-C3 lignin monomers. p-Coumaric acid is not involved in ester-ether bridges. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Related Products of 3929-47-3).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) 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, 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. 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.Related Products of 3929-47-3

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

Ghafuri, Hossein et al. published their research in Scientific Reports in 2022 | CAS: 105-13-5

(4-Methoxyphenyl)methanol (cas: 105-13-5) 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.Recommanded Product: (4-Methoxyphenyl)methanol

Copper(II)-灏?cyclodextrin immobilized on graphitic carbon nitride nanosheets as a highly effective catalyst for tandem oxidative amidation of benzylic alcohols was written by Ghafuri, Hossein;Rashidizadeh, Afsaneh;Gorab, Mostafa Ghafori;Jafari, Ghazaleh. And the article was included in Scientific Reports in 2022.Recommanded Product: (4-Methoxyphenyl)methanol This article mentions the following:

In this study, an efficient catalyst based on graphitic carbon nitride nanosheets (CN) and copper(II) supported 灏?cyclodextrin (灏綜D/Cu(II)) was synthesized and used for tandem oxidative amidation of benzylic alcs. using amine hydrochloride salts to form aryl-amides R1C(O)NR2R3 [R1 = H, 4-Cl, 4-OMe, etc.; R2 = H, Ph, Bn, etc.]. In this regard, CN was functionalized by 灏?CD/Cu(II) via 1,3-dibromopropane linker (CN-Pr-灏?CD/Cu(II)). The prepared catalyst was characterized using FT-IR, XRD, FE-SEM, EDS, TGA, ICP-OES, BET and TEM analyses. CN-Pr-灏?CD/Cu(II) could be recycled and reused five times without significant reduction in reaction efficiency. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Recommanded Product: (4-Methoxyphenyl)methanol).

(4-Methoxyphenyl)methanol (cas: 105-13-5) 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.Recommanded Product: (4-Methoxyphenyl)methanol

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

Sagane, Fumihiro et al. published their research in Electrochemistry (Tokyo, Japan) in 2022 | CAS: 112-49-2

2,5,8,11-Tetraoxadodecane (cas: 112-49-2) 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. Ethers feature bent C閳ユ彊閳ユ弲 linkages. In dimethyl ether, the bond angle is 111鎺?and C閳ユ彊 distances are 141 pm. The barrier to rotation about the C閳ユ彊 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.Synthetic Route of C8H18O4

The effect of Mg morphology on the irregular behavior of the electrochemical quartz crystal microbalance in Mg[N(CF3SO2)2]2/glyme solutions was written by Sagane, Fumihiro;Muramatsu, Akiya. And the article was included in Electrochemistry (Tokyo, Japan) in 2022.Synthetic Route of C8H18O4 This article mentions the following:

Mg plating/stripping reaction in Mg[N(CF3SO2)2]2/glyme based solution is studied by electrochem. quartz crystal microbalance method. During the cyclic voltammetry, the apparent mass decrease is observed in spite of the neg. scan. The irregular response also appears in the Mg plating reaction with low constant c.d. apply. In the cases, Mg plating takes place locally and the size of each plating is relatively large of about 50娓璵. The cross-sectional image of the plated Mg is tree-like structure, i.e., the large Mg crystal connects to the substrate with small contact area. From the results, we conclude that the specific Mg morphol. causes the restoring force to the quartz substrate, resulting in the apparent mass decrease. 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. 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. Ethers feature bent C閳ユ彊閳ユ弲 linkages. In dimethyl ether, the bond angle is 111鎺?and C閳ユ彊 distances are 141 pm. The barrier to rotation about the C閳ユ彊 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.Synthetic Route of C8H18O4

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

Driscoll, Darren M. et al. published their research in Journal of the Electrochemical Society in 2020 | 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. 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.Formula: C8H18O4

Rationalizing calcium electrodeposition behavior by quantifying ethereal solvation effects on Ca2+ coordination in well-dissociated electrolytes was written by Driscoll, Darren M.;Dandu, Naveen K.;Hahn, Nathan T.;Seguin, Trevor J.;Persson, Kristin A.;Zavadil, Kevin R.;Curtiss, Larry A.;Balasubramanian, Mahalingam. And the article was included in Journal of the Electrochemical Society in 2020.Formula: C8H18O4 This article mentions the following:

Ca-ion electrochem. systems have been pushed to the forefront of recent multivalent energy storage advances due to their use of earth-abundant redox materials and their high theor. specific densities in relation to monovalent or even other more widely explored multivalent-charge carriers. However, significant pitfalls in metal plating and stripping arise from electrolyte decomposition and can be related to the coordination environment around Ca2+ with both the neg. charged anion and the organic-aprotic solvent. In this study, we apply multiple spectroscopic techniques in conjunction with d. functional theory to evaluate the coordination environment of Ca2+ across a class of ethereal solvents. Through the combination of X-ray absorption fine structure and time-dependent d. functional theory, descriptive measures of the local geometry, coordination, and electronic structure of Ca-ethereal complexes provide distinct structural trends depending on the extent of the Ca2+-solvent interaction. Finally, we correlate these findings with electrochem. measurements of calcium tetrakis(hexafluoroisopropoxy)borate (CaBHFIP2) salts dissolved within this class of solvents to provide insight into the preferred structural configuration of Ca2+ electrolytic solutions for optimized electrochem. plating and stripping. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2Formula: 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. 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.Formula: C8H18O4

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

Peng, Xiaomei et al. published their research in Advanced Optical Materials in 2022 | CAS: 111-77-3

2-(2-Methoxyethoxy)ethanol (cas: 111-77-3) 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. 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).Computed Properties of C5H12O3

Near-Infrared OLEDs Based on Functional Pyrazinyl Azolate Os(II) Phosphors and Deuteration was written by Peng, Xiaomei;Yeh, Chia-Hsiu;Wang, Sheng Fu;Yan, Jie;Gan, Shifeng;Su, Shi-Jian;Zhou, Xiuwen;Zhang, Ye-Xin;Chi, Yun. And the article was included in Advanced Optical Materials in 2022.Computed Properties of C5H12O3 This article mentions the following:

Near-IR (NIR) emitting Os(II) complexes [Os(L1)2(PPhMe2)2] (tz1), [Os(L2)2(PPhMe2)2] (tz2), and [Os(L3)2(PPhMe2)2] (tz3), bearing dual (1H-1,2,4-triazol-5-yl)pyrazine chromophoric chelates, are successfully developed. These pyrazine chelates tzn (n = 1, 2, 3) differ by the location and number of 4-(trifluoromethyl)phenyl appendage(s) on pyrazine, and the associated Os(II) complexes exhibit bathochromic shifted emission, higher quantum yield, and increased radiative lifetime in comparison to parent complex [Os(fprtz)2(PMe2Ph)2] (tz0). Moreover, partially deuterated pyrazine chelate L1-d is prepared using post-synthetic deuteration, from which the Os(II) complex tz1 shows a photoluminescence quantum yield (PLQY) of 12.2% in co-doped 4,4閳?bis(N-carbazolyl)biphenyl (CBP) thin film at 3 wt%. Further, the partially deuterated tz1-d exhibits a notable increase in PLQY to 17.8% upon co-deposited into CBP thin film, confirming the influence of C-H(D) stretching vibrations on the non-radiative transition processes. Finally, tz1-d is demonstrated to be suitable in the fabrication of efficient NIR organic light-emitting diodes (OLEDs), from which maximum external quantum efficiency of 3.77% and maximum radiance of 24.1 W sr-1 m-2 are recorded for emission with peak maximum at 776 nm. These experiments confirm the suppression of C-H vibration caused quenching by deuteration, which should be broadly applicable to the OLED emitters, especially in the NIR region. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3Computed Properties of C5H12O3).

2-(2-Methoxyethoxy)ethanol (cas: 111-77-3) 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. 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).Computed Properties of C5H12O3

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

Horwitz, Gabriela et al. published their research in Physical Chemistry Chemical Physics in 2020 | CAS: 112-49-2

2,5,8,11-Tetraoxadodecane (cas: 112-49-2) 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. 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.SDS of cas: 112-49-2

Electrochemical stability of glyme-based electrolytes for Li-O2 batteries studied by in situ infrared spectroscopy was written by Horwitz, Gabriela;Calvo, Ernesto J.;Mendez De Leo, Lucila P.;de la Llave, Ezequiel. And the article was included in Physical Chemistry Chemical Physics in 2020.SDS of cas: 112-49-2 This article mentions the following:

In situ subtractively normalized Fourier transform IR spectroscopy (SNIFTIRS) experiments were performed simultaneously with electrochem. experiments relevant to Li-air battery operation on gold electrodes in two glyme-based electrolytes: diglyme (DG) and tetraglyme (TEGDME), tested under different operational conditions. The results show that TEGDME is intrinsically unstable and decomposes at potentials between 3.6 and 3.9 V vs. Li+/Li even in the absence of oxygen and lithium ions, while DG shows a better stability, and only decomposes at 4.0 V vs. Li+/Li in the presence of oxygen. The addition of water to the DG based electrolyte exacerbates its decomposition, probably due to the promotion of singlet oxygen formation. 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. 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.SDS of cas: 112-49-2

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