Category: ethers-buliding-blocks

Jin, Ke;Sun, Qiangsheng;Feng, Yudi;Guo, Jia;Xu, Jiangtao;Wang, Changchun published 《Significant Influence of Alkyl Substituents in the Alicyclic Rigid Backbone on Solubility and Thermal Stability of Polyarylamide Copolymers》 in 2021. The article was appeared in 《ACS Applied Polymer Materials》. They have made some progress in their research.Safety of 3-(4-Aminophenoxy)aniline The article mentions the following:

Incorporation of alicyclic structural units in a polymer backbone holds great promises for preparing polyarylamides with superior phys. properties (solubility, optical transparency, thermal stability, etc.). In this study, the alicyclic-containing building block, tetraethyl-substituted dibenzocyclooctadiene (TE-DBCOD), was integrated into the backbone of polyarylamides through a unique diamine monomer, TE-DBCOD-NH₂. The TE-DBCOD-containing polyarylamides were synthesized first through polycondensation with different contents of TE-DBCOD units. Compared to the control polymers without DBCOD or Et side-chain units, the polyarylamides with TE-DBCOD units showed better solubility in less polar solvents (m-cresol, pyridine, and tetrahydrofuran) and higher glass transition temperature (T_g), which provides an opportunity to fabricate polyarylamides with both improved solubility and T_g. Meanwhile, we also prepared the poly(amide-imide)s with TE-DBCOD by a two-step method for comparison. In contrast, the aromatic poly(amide-imide)s showed better solubility and lower T_gs than the corresponding aromatic poly(amide-imide)s without TE-DBCOD contents, which revealed the complex influence of structure parameters on different polymers. Addnl., the synthesized polymers possessed high thermal stability (5% weight loss temperature > 440°C) verified by thermogravimetric anal. The strategy of introducing short side chains in polymer backbones opens a window for exploration of polymers with improved solubility and increased T_g simultaneously, which also facilitates the understanding of the structure-property relationship of polymers with alicyclic structural units. And 3-(4-Aminophenoxy)aniline (cas: 2657-87-6) was used in the research process.

3-(4-Aminophenoxy)aniline is one of ethers-buliding-blocks. 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. Safety of 3-(4-Aminophenoxy)aniline The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.

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

Formula: C15H16O2In 1995, Mori, Yuji;Asai, Motoya;Okumura, Akiko;Furukawa, Hiroshi published 《Total synthesis of the polyene macrolide antibiotic roxaticin. I. Synthesis of the polyol fragment of roxaticin using a four-carbon chain extension strategy》. 《Tetrahedron》published the findings. The article contains the following contents:

The C11-C26 polyol fragment, I, of roxaticin containing eight chiral centers has been prepared in a reiterative manner using coupling reactions of chiral dithianes and epoxides followed by stereoselective reductionDimethoxydiphenylmethane (cas: 2235-01-0) were involved in the experimental procedure.

For example, the most common synthesis of ethers involves the attack of an alkoxide ion on an alkyl halide. This method is called Williamson ether synthesis.Formula: C15H16O2

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

Zaitsev, B. A.;Kleptsova, L. G.;Shvabskaya, I. D. published 《Heat-resistant network copolymers based on rolivsans modified with aromatic diamines》 in 2017. The article was appeared in 《Russian Journal of Applied Chemistry》. They have made some progress in their research.Application In Synthesis of 3-(4-Aminophenoxy)aniline The article mentions the following:

Thermochem. transformations of rolivsans with aromatic diamines were studied by IR and NMR (¹H, ¹³C) spectroscopy and by dynamic mech., thermal, and elemental anal. The heat resistance of rolivsans is considerably enhanced by their modification with small additions (10±5%) of an aromatic diamine with curing at 150-300 (320)°C. The experimental procedure involved many compounds, such as 3-(4-Aminophenoxy)aniline (cas: 2657-87-6) .

3-(4-Aminophenoxy)aniline is one of ethers-buliding-blocks. Ethers lack the hydroxyl groups of alcohols. Without the strongly polarized O―H bond, ether molecules cannot engage in hydrogen bonding with each other. Application In Synthesis of 3-(4-Aminophenoxy)anilineEthers do have nonbonding electron pairs on their oxygen atoms, however, and they can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds.

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

Winters, Jonas;Dehaen, Wim;Binnemans, Koen published 《γ-Valerolactone-based organic electrolyte solutions: a benign approach to polyaramid dissolution and processing》. The research results were published in《Green Chemistry》 in 2020.Computed Properties of C12H12N2O The article conveys some information:

Polyaramids are polymers that consist of aromatic repeating units that are connected via amide bonds. From their chem. structure, an extensive intermol. hydrogen-bond network arises, which makes them very difficult to dissolve in conventional organic solvents. A commonly used solvent system is N-methylpyrrolidone (NMP) mixed with CaCl2, where the chloride ions can break up the intermol. hydrogen bonds. Organic electrolyte solutions (OESs) are proposed as a green alternative solvent system. OESs are created by diluting ionic liquids (ILs) with an organic co-solvent. gamma-Valerolactone (GVL) was selected as a green, renewable co-solvent. The solubility in OESs was tested for three commonly produced polyaramids: poly-p-phenylene terephthalamide (PPTA), poly-m-phenylene isophthalamide (PMIA) and copoly(p-phenylene/3,4′-diphenylether terephthalamide) (ODA/PPTA). Some OESs were excellent solvents for PMIA and ODA/PPTA, with [C8MIm][Cl]/GVL yielding solubilities as high as 23.7 wt% and 7.4 wt%, resp., rivalling the currently used solvent systems. PPTA, on the other hand, was completely insoluble in all OESs. GVL was found to work synergistically with ILs, while acetonitrile and ethanol acted as a non-solvent and anti-solvent, resp. OESs made from GVL and imidazolium ILs were suitable solvents for fiber spinning, as was demonstrated using a 3D-printed spinning setup. The Kamlet-Taft parameters of the OES were determined from which boundary conditions for dissolution To complete the study, the researchers used 3-(4-Aminophenoxy)aniline (cas: 2657-87-6) .

3-(4-Aminophenoxy)aniline is one of ethers-buliding-blocks. Ethers lack the hydroxyl groups of alcohols. Without the strongly polarized O―H bond, ether molecules cannot engage in hydrogen bonding with each other. Computed Properties of C12H12N2OEthers do have nonbonding electron pairs on their oxygen atoms, however, and they can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds.

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

Jiang, Yan;Yin, Hong-liang;Wang, Li-li;Sun, Xiao-qiang published 《Synthesis of heterocyclic ethers chiral ligands》 in 2014. The article was appeared in 《Huaxue Shiji》. They have made some progress in their research.Application In Synthesis of Dimethoxydiphenylmethane The article mentions the following:

Using L-tartaric acid and benzophenone as reactants, a family of heterocyclic ether chiral ligands ((4S,5S)-2,2-diphenyl-5-((pyridin-2-ylmethoxy) methyl)-1,3-dioxolane-4-yl) methanol I and 2,2′-((((4S, 5S)-2,2-dip-henyl-1,3-dioxolane-4,5-diyl) bis (methylene)) bis (oxy) bis (methylene)) dipyridine II were synthesized via esterification, ketal and reduction reactions. There were two methene groups between the chiralcenter and the ligand atoms, this increased the flexible of chiral ligands, and the catalytic performance was primarily discussed. The experimental procedure involved many compounds, such as Dimethoxydiphenylmethane (cas: 2235-01-0) .

Dimethoxydiphenylmethane is one of ethers-buliding-blocks. 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. Application In Synthesis of Dimethoxydiphenylmethane The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.

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

Synthetic Route of C12H12N2O《Studies of formation mechanism, structure, and properties of network copolymers obtained by cocuring of rolivsan thermosetting resins with aromatic diamines》 was published in 2019. The authors were Zaitsev, B. A.;Kleptsova, L. G.;Shvabskaya, I. D., and the article was included in《International Journal of Polymer Science》. The author mentioned the following in the article:

Rolivsan thermosetting resins (ROLs) demonstrate high glass-transition temperatures and excellent processability. In our work, high-temperature properties of ROLs were significantly improved using a novel technique for structural and chem. modification of microheterogeneous network polymers. This technique involves, among other procedures, cocuring of rolivsan resins with aromatic diamines (ADA). The most noticeable increase in storage moduli and glass transition temperatures (T_g) of these copolymers was achieved when ROLs were modified with 10-15 weight% of ADA and the resulting blends were subjected to thermal treatment in air in the temperature range 180 to 320°C for several hours. FTIR, ¹³C NMR spectroscopy, and dynamic mech. and thermal analyzes were used for studying the structure and properties of the obtained products. It was demonstrated that the mechanism of formation of ROL-ADA copolymers includes the following high-temperature reactions: (i) three-dimensional radical copolymerization of unsaturated ROL components and (ii) cleavage of heat-sensitive methacrylate crosslinking units inside the polymer network. The second process is accompanied by formation of pending units of methacrylic acid and methacrylic anhydride, which participate in condensation reactions with ADA.3-(4-Aminophenoxy)aniline (cas: 2657-87-6) were involved in the experimental procedure.

3-(4-Aminophenoxy)aniline is one of ethers-buliding-blocks. 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. Synthetic Route of C12H12N2O The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.

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

Franchini, Silvia;Sorbi, Claudia;Linciano, Pasquale;Carnevale, Gianluca;Tait, Annalisa;Ronsisvalle, Simone;Buccioni, Michela;Del Bello, Fabio;Cilia, Antonio;Pirona, Lorenza;Denora, Nunzio;Iacobazzi, Rosa Maria;Brasili, Livio published 《1,3-Dioxane as a scaffold for potent and selective 5-HT_1AR agonist with in-vivo anxiolytic, anti-depressant and anti-nociceptive activity》. The research results were published in《European Journal of Medicinal Chemistry》 in 2019.Application of 2235-01-0 The article conveys some information:

A series of compounds generated by ring expansion/opening and mol. elongation/simplification of the 1,3-dioxolane scaffold were prepared and tested for binding affinity at 5-HT_1AR and α₁ adrenoceptors. The compounds with greater affinity were selected for further functional studies. N-((2,2-diphenyl-1,3-dioxan-5-yl)methyl)-2-(2-methoxyphenoxy)ethan-1-ammonium hydrogen oxalate I emerged as highly potent full agonist at the 5-HT_1AR (pKi 5-HT_1A = 8.8; pD₂ = 9.22, %E_max = 92). The pharmacokinetic data in rats showed that the orally administered I has a high biodistribution in the brain compartment. Thus, I was further investigated in-vivo, showing an anxiolytic and antidepressant effect. Moreover, in the formalin test, the above compound was able to decrease the late response to the noxious stimulus, indicating a potential use in the treatment of chronic pain. And Dimethoxydiphenylmethane (cas: 2235-01-0) was used in the research process.

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.Application of 2235-01-0

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

SDS of cas: 2235-01-0《Product subclass 7: organometallic compounds of potassium》 was published in 2006. The authors were Mordini, Alessandro;Valacchi, M., and the article was included in《Science of Synthesis》. The author mentioned the following in the article:

A review of the preparation and application of potassium organometallic compounds in organic synthesis. To complete the study, the researchers used Dimethoxydiphenylmethane (cas: 2235-01-0) .

Dimethoxydiphenylmethane is one of ethers-buliding-blocks. 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. SDS of cas: 2235-01-0 The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.

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

Hasegawa, Masatoshi;Fujii, Mari;Wada, Yuriko published 《Approaches to improve the film ductility of colorless cycloaliphatic polyimides》 in 2018. The article was appeared in 《Polymers for Advanced Technologies》. They have made some progress in their research.Application In Synthesis of 3-(4-Aminophenoxy)aniline The article mentions the following:

This study described approaches for improving the film ductility of colorless cycloaliphatic polyimides (PIs). An unexpected toughening effect was observed when a PI derived from pyromellitic dianhydride (PMDA) and 4,4′-methylenebis(cyclohexylamine) was modified by copolymerization with a low isophoronediamine (IPDA) content of 5 to 30 mol%, despite there being no film-forming ability in the homo PMDA/IPDA system. For example, at an IPDA content of 20 mol%, the copolymer showed significantly improved film toughness (maximum elongation at break, ε_b max = 57%), excellent optical transparency (light transmittance at 400 nm, T₄₀₀ = 83.7%), and a high glass transition temperature (T_g = 317°C). This toughening effect can be interpreted on the basis of the concept of chain slippage. In this study, the PIs derived from bicyclo[2.2.2]octane-2,3,5,6-tetracarboxylic dianhydride (H-BTA) with various diamines were also systematically investigated to evaluate the potential of H-BTA-derived systems. The combinations of H-BTA with ether-containing diamines led to highly tough PI films (ε_b max > 100%) with very high T_gs, strongly contrasting with the results of an earlier study. The observed excellent properties are related to the steric structure of H-BTA. Our interest also extended to the solution processability. A copolyimide derived from H-BTA with a sulfone-containing diamine and an ether-containing diamine achieved a very high optical transparency (T₄₀₀ = 86.8%), a very high T_g (313°C), and good ductility (ε_b max = 51%) while maintaining solution processability. Thus, these approaches enabled us to dramatically improve the ductility of cycloaliphatic PI films that have, to date, been considered brittle. To complete the study, the researchers used 3-(4-Aminophenoxy)aniline (cas: 2657-87-6) .

3-(4-Aminophenoxy)aniline is one of ethers-buliding-blocks. Ethers lack the hydroxyl groups of alcohols. Without the strongly polarized O―H bond, ether molecules cannot engage in hydrogen bonding with each other. Application In Synthesis of 3-(4-Aminophenoxy)anilineEthers do have nonbonding electron pairs on their oxygen atoms, however, and they can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds.

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

Safety of DimethoxydiphenylmethaneIn 2017, Wu, Zhiyong;Leboeuf, David;Retailleau, Pascal;Gandon, Vincent;Marinetti, Angela;Voituriez, Arnaud published 《Enantioselective gold(I)-catalyzed rearrangement of cyclopropyl-substituted 1,6-enynes into 2-oxocyclobutyl-cyclopentanes》. 《Chemical Communications (Cambridge, United Kingdom)》published the findings. The article contains the following contents:

A gold(I)-catalyzed cycloisomerization/ring expansion sequence allows the highly enantioselective synthesis of 2-oxocyclobutylcyclopentane derivatives from cyclopropyl-substituted enynes [e.g., I → cis-II + trans-III (87%, cis/trans = 4.9/1, 99% ee cis) when conducted in wet toluene]. The bimetallic [(R)-MeO-DTBM-BIPHEP-(AuCl)₂] complex was found to be the best precatalyst, affording the desired cyclobutanones in high yields and enantioselectivities (up to 99% ee). The usefulness of the method was further demonstrated by preparing the tricyclic core scaffold of russujaponol D (IV). And Dimethoxydiphenylmethane (cas: 2235-01-0) was used in the research process.

For example, the most common synthesis of ethers involves the attack of an alkoxide ion on an alkyl halide. This method is called Williamson ether synthesis.Safety of Dimethoxydiphenylmethane

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