Month: February 2023

A Mild and Ligand-Free Ni-Catalyzed Silylation via C-OMe Cleavage was written by Zarate, Cayetana;Nakajima, Masaki;Martin, Ruben. And the article was included in Journal of the American Chemical Society in 2017.SDS of cas: 365564-07-4 This article mentions the following:

Metal-catalyzed transformations that forge carbon-heteroatom bonds are of central importance in organic synthesis. Despite the formidable potential of aryl Me ethers as coupling partners, the scarcity of metal-catalyzed C-heteroatom bond formations via C-OMe cleavage is striking, with isolated precedents requiring specialized, yet expensive, ligands, high temperatures, and π-extended backbones. Authors report an unprecedented catalytic ipso-silylation of aryl Me ethers under mild conditions and without recourse to external ligands. The method is distinguished by its wide scope, which includes the use of benzyl Me ethers, vinyl Me ethers, and unbiased anisole derivatives, thus representing a significant step forward for designing new C-heteroatom bond formations via C-OMe scission. Applications of this transformation in orthogonal silylation techniques as well as in further derivatizations are also described. Preliminary mechanistic experiments suggest the intermediacy of Ni(0)-ate complexes, leaving some doubt that a canonical catalytic cycle consisting of an initial oxidative addition of the C-OMe bond to Ni(0) species comes into play. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4SDS of cas: 365564-07-4).

2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4) 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).SDS of cas: 365564-07-4

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

Friedlander synthesis of substituted quinolines from N-pivaloylanilines was written by Ubeda, J. Ignacio;Villacampa, Mercedes;Avendano, Carmen. And the article was included in Synthesis in 1998.Product Details of 56619-93-3 This article mentions the following:

Quinolines were synthesized by lithiation of N-pivaloylanilines with sec-BuLi, formylation with DMF, and subsequent condensation with active methylene groups of aldehydes or ketones (KHMDS). The pivaloyloxy group is eliminated during the 1-pot procedure in most cases. The scope of the reaction was studied, showing that the method is limited by the nature of intermediate compounds In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Product Details of 56619-93-3).

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

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

A bagasse-supported magnetic manganese dioxide nanoparticle: applications in the selective aerobic oxidation of alcohols and one-pot tandem oxidative synthesis of quinazolinones was written by Rashidi Vahid, Adina;Hajishaabanha, Fatemeh;Shaabani, Shabnam;Farhid, Hassan;Shaabani, Ahmad. And the article was included in Journal of the Iranian Chemical Society in 2022.HPLC of Formula: 105-13-5 This article mentions the following:

Magnetic manganese dioxide nanoparticles (MnO₂-Fe₃O₄) were coated on sugarcane bagasse as a sugar industrial waste and bio-support (MnO₂-Fe₃O₄@bagasse) via an in situ reduction strategy, in which potassium permanganate was used as the precursor of MnO₂ and sugarcane bagasse as a bio-support and reducing agent of KMnO4. The synthesized bio-based catalyst was characterized by X-ray diffraction, thermogravimetric anal., inductively coupled plasma optical emission spectroscopy, SEM, energy dispersive spectroscopy, Brunauer-Emmett-Teller surface area anal., and vibrating sample magnetometer anal. The catalyst was successfully utilized in the selective aerobic oxidation of primary and secondary benzylic alcs. R¹CH(OH)R² (R¹ = Ph, 4-nitrophenyl, 2,4-dichlorophenyl, 3-phenylpropyl, etc.; R² = H, Me, Ph, 2-oxo-2-phenylethyl) to their corresponding carbonyl compounds R¹C(O)R² and one-pot tandem oxidative synthesis of 2-(substituted)quinazoline-4(3H)-ones I (R³ = Ph, 3-methoxyphenyl, 4-nitrophenyl, 2,4-dichlorophenyl, etc.) from the o-aminobenzamide and aromatic alcs. R³CH₂OH in the absence of oxidizing reagent or initiator. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5HPLC of Formula: 105-13-5).

(4-Methoxyphenyl)methanol (cas: 105-13-5) 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 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.HPLC of Formula: 105-13-5

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

Reducing Cellulose Crystallinity with a Noncellulose-Dissolving Solid Zwitterion and Its Application for Biomass Pretreatment was written by Hachisu, Ayumi;Tobe, Hitomi;Ninomiya, Kazuaki;Takahashi, Kenji;Kuroda, Kosuke. And the article was included in ACS Sustainable Chemistry & Engineering in 2022.Category: ethers-buliding-blocks This article mentions the following:

One-pot ethanol production from plant biomass (successive biomass pretreatment, enzymic hydrolysis, and fermentation in a single vessel) is necessary for the practical production of second-generation bioethanol because multipot procedures require large energy inputs. One-pot ethanol production requires low-toxicity cellulose solvents, and liquid zwitterions are the most promising candidates. However, liquid zwitterions have complex synthetic procedures, which significantly increases the energy cost. Here, the applicability of low-toxic simple zwitterions was investigated from the viewpoint of pretreatment ability for one-pot ethanol production In this study, a simple solid noncellulose dissolving zwitterion was able to reduce the crystallinity of microcrystalline cellulose. The pretreatment of cellulose was performed in a zwitterion/water mixture at 100° while removing water. The imidazolium cation and carboxylate anion are key structures for an efficient pretreatment. Cellulose pretreated with the solid zwitterion was susceptible to hydrolysis, and the hydrolysis efficiency was comparable to that of the liquid zwitterion, which dissolves cellulose. The simple solid zwitterion was also effective for biomass pretreatment. The zwitterion delignified as well as reduced crystallinity, resulting in the pretreatment of bagasse. The pretreatment ability for bagasse was comparable to that of liquid zwitterions. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3Category: ethers-buliding-blocks).

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. 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.Category: ethers-buliding-blocks

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

Synthesis of Et quininate from m-cresol was written by Koelsch, C. F.. And the article was included in Journal of the American Chemical Society in 1944.Related Products of 5367-32-8 This article mentions the following:

m-MeC₆H₄OH (54 g.) in 150 ml. AcOH and 20 ml. H₂SO₄, treated at 8-10° with 35 g. NaNO₂ in a little H₂O, gives the NO compound; this was added to 50 ml. HNO₃ and 150 ml. H₂O at 40-50° and the crude NO₂ compound was treated with Me₂SO₄ and NaOH to give 50-6 g. of 3,4-Me(O₂N)C₆H₃OMe (I), m. 55°. I and (CO₂Et)₂ with EtONa in ether, heated 4 hrs. at 45°, treated with ice H₂O and then with 30% NaOH and H₂O₂, give 71-6% of 5-methoxy-2-nitro-α-toluic acid (II); reduction of the K salt of II in H₂O with Raney Ni at 30-lb. H pressure gives the the corresponding amino acid, m. 122-4° (decomposition), distillation of which yields 5-methoxyoxindole (III), pale pink, m. 152-4°. II with EtOH-HCl gives 55% of the Et ester (IV), pale yellow, b₁ 185°, m. 57-9°. Reduction of IV with Raney Ni and H at 30-lb. pressure gives Et 2-amino-5-methoxy-α-toluate (V), whose Ac derivative m. 104-5°; distillation of IV gives III. V with (CHO)₂ at 25° gives 88% of glyoxal bis(2-carbethoxymethyl)-4-methoxyanil (VI), yellow, m. 108-9°. VI (7 g.) and 1 g. Na in 20 ml. EtOH, boiled 5 min. and acidified with 3 ml. AcOH, give 0.3 g. of Et quininate (VII), m. 65-7°. The action of C₅H₅N, piperidine or K₂CO₃ in hot quinoline yields no VII. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Related Products of 5367-32-8).

3-Methyl-4-nitroanisole (cas: 5367-32-8) 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. 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.Related Products of 5367-32-8

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

[1,3,4]Thiadiazolo[2,3-c][1,2,4]triazines was written by Gakhar, H. K.;Prabha, Usha;Gill, J. K.. And the article was included in Journal of the Indian Chemical Society in 1984.Product Details of 57179-35-8 This article mentions the following:

The cyclocondensation of aminotriazinethiones I (R = Me, Ph) with R¹CHO [R¹ = Ph, O₂NC₆H₄, (un)substituted 3,4-(methylenedioxy)phenyl, HO(MeO)C₆H₃] gave thiadiazolotriazines II. I (R = Me) in ether was treated with HCl gas, the ether was decanted, the residue was placed in EtOH, PhCHO and NaOAc were added, and the mixture was refluxed to give II (R = Me, R¹ = Ph). In the experiment, the researchers used many compounds, for example, 3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8Product Details of 57179-35-8).

3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8) 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).Product Details of 57179-35-8

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

Palladium(II)-Catalyzed Direct ortho-C-H Acylation of Anilides by Oxidative Cross-Coupling with Aldehydes using tert-Butyl Hydroperoxide as Oxidant was written by Chan, Chun-Wo;Zhou, Zhongyuan;Yu, Wing-Yiu. And the article was included in Advanced Synthesis & Catalysis in 2011.Quality Control of N-(3-Methoxyphenyl)pivalamide This article mentions the following:

An efficient palladium-catalyzed C-H acylation with aldehydes using tert-Bu hydroperoxide (TBHP) transforms various anilides into synthetically useful 2-aminobenzophenone derivatives under mild conditions (40°, 3 h). The acylation reaction exhibits excellent regioselectivity and functional group tolerance, and simple aromatic aldehydes, functionalized aliphatic aldehydes and heteroaromatic aldehydes are effective coupling partners. The acylation reaction is probably initiated by a rate-limiting electrophilic C-H cyclopalladation (k_H/k_D=3.6; ρ⁺=-0.74) to form an arylpalladium complex, followed by acyl radical functionalization. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Quality Control of N-(3-Methoxyphenyl)pivalamide).

N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) 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 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.Quality Control of N-(3-Methoxyphenyl)pivalamide

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

Cross-Coupling in Flow using Supported Catalysts: Mild, Clean, Efficient and Sustainable Suzuki-Miyaura Coupling in a Single Pass was written by Munoz, Juan de M.;Alcazar, Jesus;de la Hoz, Antonio;Diaz-Ortiz, Angel. And the article was included in Advanced Synthesis & Catalysis in 2012.Recommanded Product: 365564-07-4 This article mentions the following:

A mild, clean, practical, sustainable and high yielding procedure for Suzuki-Miyaura cross-coupling in a single pass using a silica-supported palladium catalyst is described. The catalyst can be used in more than 30 reactions and for more than 8 h of continuous processing without a decrease in reactivity due to the low leaching observed Different halides/pseudo-halides and organoboron compounds can be used without modifying the standard procedure. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4Recommanded Product: 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. 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: 365564-07-4

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

A One-Pot Synthesis of “K(hfa) glyme” Adducts: Effect of the Polyether Length on the Ion Coordination Sphere was written by Peddagopu, Nishant;Sanzaro, Salvatore;Rossi, Patrizia;Paoli, Paola;Malandrino, Graziella. And the article was included in European Journal of Inorganic Chemistry in 2021.SDS of cas: 112-49-2 This article mentions the following:

Potassium complexes are starting to gather more and more interest from academia and industry because of their intriguing application possibilities. Novel adducts of potassium hexafluoroacetylacetonato [K(hfa)] with polyethers (monoglyme, diglyme, triglyme, and tetraglyme) were synthesized through a single step reaction and characterized through FTIR spectroscopy as well as ¹H and ¹³C NMR spectroscopy. Single crystal x-ray diffraction studies enabled the identification of fascinating K coordination polymeric networks. 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. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. 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.SDS of cas: 112-49-2

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

Synthesis and characterization of aryloxy derivatives of bis-azetinone for anticancer activity was written by Pramila, T.. And the article was included in Journal of Pharmaceutical Sciences and Research in 2020.Related Products of 1877-75-4 This article mentions the following:

A series of novel aryloxy bis azetinones have been synthesized using benzocaine as a starting compound Benzocaine reacted with benzyl bromide to give N-benzylated benzocaine which underwent nucleophillic addition reaction with hydrazine hydrate to yield 4-(benzylamino)benzohydrazide, further treatment with palladium catalyst gave 4-aminobenzohydrazide. 4-Aminobenzohydrazide was reacted with benzaldehyde to yield (4E,10E)-N’-benzylidene-4-(benzylideneamino)benzohydrazide, which on further reacting with different substituted phenoxyacetyl chlorides gave aryloxy bis azetinone derivatives I (R = H, 4-OMe, 3-Br, etc.). The synthesized compounds were screened for in-vitro anticancer activity and were found to be active. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Related Products of 1877-75-4).

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. 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).Related Products of 1877-75-4

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