Ethers-buliding-blocks

Water behavior of current jet fuel versus operating conditions: Storage time, temperature, relative humidity and anti-icing agent was written by Chen, Teng;Xu, Xin;Hu, Jianqiang;Guo, Li;Yang, Shizhao;Zhao, Tianxiang;Ma, Jun. And the article was included in Fuel in 2022.Quality Control of 2-(2-Methoxyethoxy)ethanol This article mentions the following:

Water contamination in aviation jet fuel has been a particular concern throughout the aviation industry for many decades on account of any contaminating water may accelerate the corrosion of the aircraft fuel systems, diminish the lubricative properties of the fuel, promote microorganism growth, and more importantly, pose threat to flight safety. However, the water behavior of jet fuel has not been studied systematically so far, especially for the free water, which is the main factor that causes the hazards mentioned above. Herein, the water behaviors, including dissolved and free water behaviors vs. storage time, temperature, relative humidity and anti-icing agent are investigated. Compared with storage time, temperature and relative humidity have a greater influence on the water solubility, and the resp. exponential and linear relationships between the solubility of water and temperature and relative humidity are identified in this paper. Furthermore, a complete discussion is carried out on the effect of anti-icing agent on the solubility of water and free water content in jet fuel. More importantly, the real water behavior of jet fuel with anti-icing agent is also studied through simulating the variation in temperature during flight. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3Quality Control of 2-(2-Methoxyethoxy)ethanol).

2-(2-Methoxyethoxy)ethanol (cas: 111-77-3) 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.Quality Control of 2-(2-Methoxyethoxy)ethanol

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

2-Substituted-5-nitropyrimidines by the condensation of sodium nitromalonaldehyde with amidines was written by Fanta, Paul E.;Hedman, Edward A.. And the article was included in Journal of the American Chemical Society in 1956.Application of 51488-33-6 This article mentions the following:

p-MeC₆H₄C(:NH)NH₂ (I) (1.86 g.) and 1.57 g. Na[C(NO₂)(CHO)₂] (II) mixed in 25 cc. H₂O at room temperature gave I-II salt, fine white needles, m. 148-50° (from H₂O), which, heated 2 h. at 70° in aqueous Triton B, yielded 5-nitro-2-p-tolylpyrimidine (III), m. 217°. PhC(:NH)NH₂.HCl (IIIa) and II mixed in H₂O at room temperature darkened and resinified on standing and the product was characterized only by conversion to 5-nitro-2-phenylpyrimidine (IV) on heating in aqueous Triton B. IIIa.2H₂O and II.H₂O heated 4 h. with aqueous Triton B at 70° gave 79% IV; IIIa and II heated similarly with aqueous K₂CO₃ gave 66% IV and with aqueous NaOH 42% IV (NH₃ evolved during the reaction); II and IIIa refluxed 4 h. with aqueous NaOH gave no IV but NH₃ was evolved during the reaction and BzOH was isolated from the mixture II and IIIa heated 15 min. at 80° with Ac₂O-pyridine yielded 85% IV; a similar run but without the pyridine gave only 40% IV. II and IIIa refluxed 2 h. with EtOH and NaOEt, or kept 12 h. at 0° with alc. HCl gave no IV. IIIa.2H₂O.HCl (1.94 g.) and 1.57 g. II in 25 cc. H₂O treated with 1 cc. Triton B, heated 4 h. at 65-70°, and refrigerated overnight yielded 1.50 g. IV, pale tan microcrystals, m. 222-3.5°. II (2.8 g.) mixed intimately with 1.8 g. MeC(:NH)NH₂.HCl, treated with a few drops piperidine, heated 1 h. on the steam bath, treated with 1 g. Na₂CO₃, heated 0.5 h., dissolved in a small amount of H₂O, the solution cooled, filtered, and the residue extracted with ligroine gave less than 1% 2-methyl-5-nitropyrimidine, m. 186-7° (from ligroine); a similar run with NaOH in EtOH gave no better yields. II treated with concentrated NH₄OH or with NH₄Cl, NH₄OAc, or AcNH₂ in the presence of Triton B gave an intractable resin. The appropriate nitrile (0.5 mol) and 0.5 mol absolute MeOH treated with a slight excess of dry HCl in 25 cc. absolute Et₂O, and the resulting solid imidic ester HCl salt decomposed with 10% NH₃ in absolute MeOH gave the corresponding amidines which were isolated as their HCl salts and converted by the method described for the preparation of III to the corresponding 2-substituted-5-nitropyrimidines (V); in this manner were prepared the following arylamidine HCl salts and V (aryl group of amidine = 2-substituent of V, m.p. of amidine HCl salt, m.p. and % yield of V given): Ph, 70-3°, 222-3.5°, 79; p-MeC₆H₄, 215-16°, 249-50°, 87; p-MeOC₆H₄, 216-18°, 216-18°, 30; p-BrC₆H₄, 261-3°, 225-7°, 89; p-ClC₆H₄, 240-4°, 170-1.5°, 81; p-FC₆H₄, 209-11°, 154-5°, 71; p-O₂NC₆H₄, 294-5°, 235-7°, 48; p-H₂NO₂SC₆H₄, 207-9°, 268-70°, 41; p-PhC₆H₄, 245-9°, 253-4°, 85; m-O₂NC₆H₄, 238-42°, 133-4°, 79; 3,4-(MeO)₂C₆H₃, 234°, 182-3°, 67; 3-C₅H₄N, 190-4°, 202-3°, 36; PhCH₂, 151-3°, 170°, 77 (picrate, m. 228-30°); 3,4-(MeO)₂C₆H₃CH₂, 153-5°, 235°, 38; PhCH:CH, 68-70°, 219-20°, 81; BzCH₂, -, 210-11°, 70 (free amidine, m. 185-7°). The following aliphatic amidine HCl salts (alkyl group and m.p. given) did not condense with II: Me, 164-6°; Bu, oil (picrate, m. 193-5°); C₁₁H₂₃, 125-7°; MeCH(OH), 162-6°; HOCH₂CH₂, 81-2°. IV (0.20 g.) in 0.40 g. NaOH in 10 cc. H₂O treated with warming and stirring with 1.05 g. Na₂S₂O₄, centrifuged to remove a small amount of brown solid, cooled to 5°, and treated with 2 cc. Ac₂O yielded the 5-AcNH analog of IV, shiny white platelets, m. 208-9° (from 20% aqueous EtOH). IV (2.00 g.) in 200 cc. absolute EtOH hydrogenated 0.5 h. at room temperature and 3 atm. pressure over 0.6 g. 5% Pd-C, the suspension evaporated to dryness in vacuo on the steam bath, the residue extracted with boiling C₆H₆, and the extract cooled yielded 1.50 g. 5-amino-2-phenylpyrimidine (VI), m. 90.5-92°. Similarly was obtained 5-amino-2-(p-tolyl)pyrimidine, 95%, m. 183.5-84°. VI diazotized under various conditions and each reaction mixture tested for the presence of aromatic diazonium salt with an alk. solution of 2-C₁₀H₇OH in no case gave a color. In the experiment, the researchers used many compounds, for example, 3,4-Dimethoxybenzimidamide hydrochloride (cas: 51488-33-6Application of 51488-33-6).

3,4-Dimethoxybenzimidamide hydrochloride (cas: 51488-33-6) 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.Application of 51488-33-6

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

High hypolipidemic activity of saturated side-chain α-asarone analogs was written by Cruz, Adriana;Garduno, Leticia;Salazar, Maria;Martinez, Elizdath;Diaz, Francisco;Chamorro, German;Tamariz, Joaquin. And the article was included in Medicinal Chemistry Research in 2001.SDS of cas: 3929-47-3 This article mentions the following:

With the aim of evaluating the pharmacophore potential of the side chain of α-asarone regarding its high hypolipidemic activity, α-asarone analogs (I) were evaluated pharmacol. For I, with a variable-size side chain, significant decreases in serum cholesterol, LDL-cholesterol, and triglyceride levels and significant increases in HDL-cholesterol levels were observed in mice. I were even more active than α-asarone in reducing cholesterol. The results suggested that the length and saturated character of the side chain seem to be a key feature in improving hypolipidemic activity of I. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3SDS of cas: 3929-47-3).

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

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

Ru-Catalyzed Hydrogenolysis of Lignin: Base-Dependent Tunability of Monomeric Phenols and Mechanistic Study was written by Li, Helong;Song, Guoyong. And the article was included in ACS Catalysis in 2019.Electric Literature of C11H16O3 This article mentions the following:

Substantial attention has been given to depolymerization of lignin into monomeric phenols in recent years because lignin is a renewable and CO₂-natural aromatic resource. Recent results indicated that the base can shift the selectivity from C3-fragmented phenols to C2-fragmented phenols partially in transition metal-catalyzed lignin hydogenolysis, while reaction mechanisms have remained elusive. Using a series of dimeric, trimeric, and polymeric β-O-4 lignin mimics, as well as their deuterated analogs, we now report an in-depth exptl. study on the mechanism of Ru/C-catalyzed hydogenolysis lignin. Exptl. evidence based on substrate probes, reactivity examination of possible intermediates, and isotopic labeling experiments confirmed that the reported pathways, such as enol ether generated via α,β-dehydration reaction or C_α carbonyl compounds generated via dehydrogenation or consecutive C_β-O and C_γ-OH bonds hydrogenolysis, are irrelevant to current reactions. For C3-fragmented phenols with Ru/C catalyst under neutral condition, we deduced that the monolignol such as coniferyl alc. is formed primarily through a concerted hydrogenolysis process, where C_α-O and C_β-O bonds are ruptured synchronously. For C2-fragmented phenols generated by the combination of Ru/C and Cs₂CO₃, the reaction should start from quinone methide specie generated from the dehydration (or demethanolization) reaction between phenolic proton and C_α-OH (or C_α-OMe). The followed deprotonation of C_γ-OH and the coordination of oxygen with Ru results in a Ru specie, which undergoes C_β-H, C_β-O, and C_β-C_γ bonds cleavage to release 4-vinylphenol. In the case of Ru/C-catalyzed hydrogenolysis of an enzymic mild acidolysis lignin (EMAL) derived from birch tree, the effects of some key parameters such as temperature, reaction time, as well as the type and dosage of base were also examined in terms of monomer yields and selectivity. We found the formation of C2-phenols is a base-dependent process, which is in line with the proposed mechanism. Under optimized conditions, a high proportion of C2-phenols (44%) could be obtained with 26.6 weight % total monomers yield. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Electric Literature of C11H16O3).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) 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.Electric Literature of C11H16O3

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

Synthesis of analogs of the Gwt1 inhibitor manogepix (APX001A) and in vitro evaluation against Cryptococcus spp was written by Trzoss, Michael;Covel, Jonathan A.;Kapoor, Mili;Moloney, Molly K.;Soltow, Quinlyn A.;Webb, Peter J.;Shaw, Karen Joy. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.Formula: C14H15BO4 This article mentions the following:

Fosmanogepix (APX001) is a first-in-class prodrug mol. that is currently in Phase 2 clin. trials for invasive fungal infections. The active moiety manogepix (APX001A) inhibits the novel fungal protein Gwt1. Gwt1 catalyzes an early step in the GPI anchor biosynthesis pathway. Here we describe the synthesis and evaluation of 292 new and 24 previously described analogs that were synthesized using a series of advanced intermediates to allow for rapid analoging. Several compounds demonstrated significantly (8- to 32-fold) improved antifungal activity against both Cryptococcus neoformans and C. gattii as compared to manogepix. Further in vitro characterization identified three analogs with a similar preliminary safety and in vitro profile to manogepix and superior activity against Cryptococcus spp. In the experiment, the researchers used many compounds, for example, (4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4Formula: C14H15BO4).

(4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4) 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. 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.Formula: C14H15BO4

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

Amidines in the Diels-Alder synthesis was written by Martinez, Joaquin Royo. And the article was included in Rev. real. acad. cienc. exact. fís. y nat. Madrid in 1952.SDS of cas: 51488-33-6 This article mentions the following:

Several amidines were prepared as follows. CH₂(OH)CH₂Cl + NaCN → CH₂(OH)CH₂CN (I), b₁₅ 110° (84%); I + finely divided Al (hydroquinone to eliminate polymerization) → CH₂:CHCN (II), b. 77.6-79.0° (69.3%); II + EtOH (distilled from Na), saturated with gaseous HCl → CH₂:CHC(:NH₂Cl)OEt (III), m. 104-4.5° (decomposition), stable in bottles with airtight stoppers; III in absolute EtOH + NH₃ in absolute EtOH (3 hr. agitation, followed by standing 2 days) → CH₂:CHC(:NH₂Cl)NH₂. Similarly, vanillin + NaOH + MeI → (MeO)₂C₆H₃CHO → (MeO)₂C₆H₃CH:NOH → (MeO)₂C₆H₃CN, m. 67°, → (MeO)₂C₆H₃C(:NH₂Cl)OEt, m. 141° (decomposition) → (MeO)₂C₆H₃C(:NH₂Cl)NH₂, m. 237°. Piperonal → oxime, m. 110°, → piperonylonitrile, m. 94.5°, → Et piperonylimidate-HCl, m. 122-3°, → piperonylamidine-HCl, m. 238° (decomposition) → piperonylamidine, m. 167°, → picrate, m. 257°. PhCN → m-O₂NC₆H₄CN, m. 117.5°, → m-O₂NC₆H₄C(:NH₂Cl)OEt → m-O₂NC₆H₄(:NH₂Cl)NH₂, m. 250° (decomposition). There was no reaction comparable to a Diels-Alder, between these amidines and styrene, anethole, or maleic anhydride. MeNO₂ and CH₂(OH)CN, used as solvents, were prepared by the decarboxylation of CH₂(NO₂)CO₂H and by the addition of HCN to CH₂O, resp. In the experiment, the researchers used many compounds, for example, 3,4-Dimethoxybenzimidamide hydrochloride (cas: 51488-33-6SDS of cas: 51488-33-6).

3,4-Dimethoxybenzimidamide hydrochloride (cas: 51488-33-6) 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. 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.SDS of cas: 51488-33-6

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

A novel and direct synthesis of chroman derivatives using a hypervalent iodine(III) reagent was written by Hamamoto, Hiromi;Hata, Kayoko;Nambu, Hisanori;Shiozaki, Yukiko;Tohma, Hirofumi;Kita, Yasuyuki. And the article was included in Tetrahedron Letters in 2004.SDS of cas: 3929-47-3 This article mentions the following:

The direct aromatic carbon-oxygen bond-formation reaction was described and the novel and simple synthetic method for chroman derivatives involving aromatic cation radical intermediates was developed using the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA). In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3SDS of cas: 3929-47-3).

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

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

Synthesis of substituted 2-[bis(4-hydroxyphenyl)methyl]pyridines was written by Schulz, Otto Erich;Fedders, Soenke. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 1977.Safety of (6-Methoxypyridin-2-yl)methanol This article mentions the following:

The title compounds I (R = H, R1 = 5-Me, 4-Me, 3-Me, 4-OMe, 4-Cl, 4-OCH2Ph, 4-OH, 6-OMe; R = Ac, R1 = 3-Me, 4-OMe, 4-Cl) were prepared by treating 2-methylpyridine N-oxides with Ac2O, hydrolyzing 2-acetoxymethylpyridines, oxidizing 2-hydroxymethylpyridines with SeO2, and treating 2-formylpyridines with PhOH in the presence of H2SO4. In the experiment, the researchers used many compounds, for example, (6-Methoxypyridin-2-yl)methanol (cas: 63071-12-5Safety of (6-Methoxypyridin-2-yl)methanol).

(6-Methoxypyridin-2-yl)methanol (cas: 63071-12-5) 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. 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.Safety of (6-Methoxypyridin-2-yl)methanol

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

Natural Hyperbolic Dispersion with Anisotropic Epsilon-Near-Zero and Epsilon-Near-Pole in Squaraine Molecular Film was written by Kim, Minjae;Choi, Kyu Ri;Lee, Yeon Ui;Heinrich, Benoit;Ko, Soo Young;Mathevet, Fabrice;Ribierre, Jean-Charles;D′Aleo, Anthony;Wu, Jeong Weon;Placide, Virginie. And the article was included in Advanced Optical Materials in 2021.SDS of cas: 111-77-3 This article mentions the following:

Epsilon-near-zero (ENZ) optical material has been employed in a number of novel linear and nonlinear optical applications, owing to the vanishing polarization upon an incident optical wave. In a uniaxial medium possessing hyperbolic energy-momentum dispersion of optical wave, ENZ can take place at ordinary and extraordinary permittivities. Organic thin films presenting a lamellar structure have been reported to exhibit a transverse neg. hyperbolic dispersion with ENZ at ordinary permittivity. Here, organic thin film with ENZ at extraordinary permittivity is demonstrated. Newly synthesized polymethine dye (i.e., squaraine indolenine triethyleneglycol mol.) self-organizes to form a layered structure in a pristine film, and both transverse neg. and pos. hyperbolic dispersions are observed at visible wavelengths. Anal. of tens-nanometer-thick pristine film shows that both ENZ and epsilon-near-pole (ENP) occur at longitudinal as well as transverse component of dielec. permittivity. Optical characterization of squaraine pristine film is presented, and the importance of transverse pos. hyperbolic dispersion in such monolithic thin film is discussed. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3SDS of cas: 111-77-3).

2-(2-Methoxyethoxy)ethanol (cas: 111-77-3) 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. But on the other hand, ethers undergo cleavage by reaction with acids. 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.SDS of cas: 111-77-3

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