Month: October 2022

《Borylation of Unactivated Aryl Chlorides under Mild Conditions by Using Diisopropylaminoborane as a Borylating Reagent》 was written by Guerrand, Helene D. S.; Marciasini, Ludovic D.; Jousseaume, Melissa; Vaultier, Michel; Pucheault, Mathieu. Synthetic Route of C14H21BO3 And the article was included in Chemistry – A European Journal in 2014. The article conveys some information:

The synthesis of arylboronic ester derivatives from aryl chlorides by using aryl(amino)boranes is described. Palladium-catalyzed coupling between aryl chlorides and diisopropylaminoborane leads to the formation of a C-B bond under mild conditions. A wide range of functional groups are tolerated, making this method particularly useful for the borylation of functionalized aromatics In the experiment, the researchers used many compounds, for example, 2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1Synthetic Route of C14H21BO3)

2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1) belongs to ethers.Ethers do have nonbonding electron pairs on their oxygen atoms, and they 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.Synthetic Route of C14H21BO3

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

《Cleavage of ether, ester, and tosylate C(sp3)-O bonds by an iridium complex, initiated by oxidative addition of C-H bonds. Experimental and computational studies》 was written by Kundu, Sabuj; Choi, Jongwook; Wang, David Y.; Choliy, Yuriy; Emge, Thomas J.; Krogh-Jespersen, Karsten; Goldman, Alan S.. Application of 203245-16-3 And the article was included in Journal of the American Chemical Society on April 3 ,2013. The article conveys some information:

A pincer-ligated iridium complex, [(PCP)Ir] (1, PCP = κ3-C6H3-2,6-[CH2P(tBu)2]2), is found to undergo oxidative addition of C(sp3)-O bonds of Me esters (MeO2CR’), Me tosylate (MeOTs), and certain electron-poor Me aryl ethers (MeOAr). DFT calculations and mechanistic studies indicate that the reactions proceed via oxidative addition of C-H bonds followed by oxygenate migration, rather than by direct C-O addition Thus, Me aryl ethers react via addition of the methoxy C-H bond, followed by α-aryloxide migration to give cis-[(PCP)Ir(H)(CH2)(OAr)], followed by iridium-to-methylidene hydride migration to give [(PCP)Ir(Me)(OAr)]. Me acetate undergoes C-H bond addition at the carbomethoxy group to give [(PCP)Ir(H)[κ2-CH2OC(O)Me]] which then affords [(PCP-CH2)Ir(H)(κ2-O2CMe)] (6-Me) in which the methoxy C-O bond has been cleaved, and the methylene derived from the methoxy group has migrated into the PCP Cipso-Ir bond. Thermolysis of 6-Me ultimately gives [(PCP)Ir(CH3)(κ2-O2CR)], the net product of methoxy group C-O oxidative addition Reaction of [(PCP)Ir] with species of the type ROAr, RO2CMe or ROTs, where R possesses β-C-H bonds (e.g., R = Et or isopropyl), results in formation of [(PCP)Ir(H)(OAr)], [(PCP)Ir(H)(O2CMe)], or [(PCP)Ir(H)(OTs)], resp., along with the corresponding olefin or [(PCP)Ir(olefin)] complex. Like the C-O bond oxidative additions, these reactions also proceed via initial activation of a C-H bond; in this case, C-H addition at the β-position is followed by β-migration of the aryloxide, carboxylate, or tosylate group. Calculations indicate that the β-migration of the carboxylate group proceeds via an unusual six-membered cyclic transition state in which the alkoxy C-O bond is cleaved with no direct participation by the iridium center. In the experiment, the researchers used 1,2,3-Trifluoro-4-methoxybenzene(cas: 203245-16-3Application of 203245-16-3)

1,2,3-Trifluoro-4-methoxybenzene(cas: 203245-16-3) is a member of aromaticfluorinated building blocks. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine-free commercial end products.Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials).Application of 203245-16-3

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

Recommanded Product: 324017-21-2On September 20, 2021 ,《Fluorosulfuryl Isocyanate Enabled SuFEx Ligation of Alcohols and Amines》 was published in Angewandte Chemie, International Edition. The article was written by Sun, Shoujun; Gao, Bing; Chen, Junyu; Sharpless, K. Barry; Dong, Jiajia. The article contains the following contents:

Fluorosulfuryl isocyanate (FSI, FSO2NCO) is established as a reliable bis-electrophilic linker for stepwise attachment of an alc. bearing module to an amine bearing module and thence a new module RO-C(=O)-NH-SO2-NR1R2 e.g., I is created. FSI’s isocyanate motif fuses directly and quickly with alcs. and phenols, affording fluorosulfuryl carbamates in nearly quant. yield. A new reagent and process to deliver the FSI-derived fluorosulfuryl carbamate fragment to amines are also developed. The resulting SVI-F motifs from step-1 are remarkably stable, given the great structural complexities in diverse products. In the step-2 reaction with amines, the best yield of the S-N linked products arise with water alone. This “”on water”” interfacial reactivity phenomenon is crucial, revealing the latent reactivity of SVI-F probe for potential covalent capture of proteins in vivo which is important in today’s drug discovery. The scope of the SuFEx chem. is largely expanded thereby and the facile entry to these phosphate-like connections should prove useful to click chem. across diverse fields. In the part of experimental materials, we found many familiar compounds, such as Fmoc-D-Phe(4-NH2)-OH(cas: 324017-21-2Recommanded Product: 324017-21-2)

Fmoc-D-Phe(4-NH2)-OH(cas: 324017-21-2) belongs to ethers.Although ethers resist hydrolysis, they are cleaved by hydrobromic acid and hydroiodic acid. Hydrogen chloride cleaves ethers only slowly. Recommanded Product: 324017-21-2

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

Electric Literature of C12H10O2On November 28, 2012 ,《Trimethylsilyl-Terminated Oligo(phenylene ethynylene)s: An Approach to Single-Molecule Junctions with Covalent Au-C σ-Bonds》 appeared in Journal of the American Chemical Society. The author of the article were Hong, Wenjing; Li, Hui; Liu, Shi-Xia; Fu, Yongchun; Li, Jianfeng; Kaliginedi, Veerabhadrarao; Decurtins, Silvio; Wandlowski, Thomas. The article conveys some information:

A new and efficient approach using cleaving of trimethylsilyl groups to create covalent Au-C anchoring sites was developed for single-mol. junction conductance measurements. Employing the mech. controllable break junction (MCBJ) technique in liquid, the authors demonstrate the formation of highly conducting single mol. junctions of several OPE derivatives The created junctions are mech. stable and exhibit conductances around one order of magnitude higher than those of their dithiol analogs. Extended assembly and reaction times lead to oligomerization. Combined STM imaging and gap-mode Raman experiments provide structure evidence to support the formation of covalent Au-C contacts and further oligomerization. The experimental process involved the reaction of 1,4-Diethynyl-2,5-dimethoxybenzene(cas: 74029-40-6Electric Literature of C12H10O2)

1,4-Diethynyl-2,5-dimethoxybenzene(cas: 74029-40-6) belongs to ethers.Although ethers resist hydrolysis, they are cleaved by hydrobromic acid and hydroiodic acid. Hydrogen chloride cleaves ethers only slowly. Electric Literature of C12H10O2

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

SDS of cas: 74029-40-6On November 5, 2021 ,《Butterfly-Like Triarylamines with High Hole Mobility and On/Off Ratio in Bottom-Gated OFETs》 appeared in Chemistry – A European Journal. The author of the article were Devibala, Panneerselvam; Balambiga, Balu; Mohamed Imran, Predhanekar; Bhuvanesh, Nattamai S. P.; Nagarajan, Samuthira. The article conveys some information:

Highly π-extended butterfly-shaped triarylamine dyads with aryleneethynylene spacer were constructed using an efficient synthetic route. These aryleneethynylene-bridged dyads were highly fluorescent and exhibited high HOMO levels, and low bandgaps, which are suitable for high-performance p-type OFETs. The field-effect transistors were fabricated through a solution-processable method and exhibited promising p-type performance with field-effect mobility up to 4.3 cm2/Vs and high Ion/off of 108 under ambient conditions. In the part of experimental materials, we found many familiar compounds, such as 1,4-Diethynyl-2,5-dimethoxybenzene(cas: 74029-40-6SDS of cas: 74029-40-6)

1,4-Diethynyl-2,5-dimethoxybenzene(cas: 74029-40-6) belongs to ethers. Ethers lack the hydroxyl groups of alcohols. Without the strongly polarized O―H bond, ether molecules cannot engage in hydrogen bonding with each other. SDS of cas: 74029-40-6

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

Herdman, Christine A.; Devkota, Laxman; Lin, Chen-Ming; Niu, Haichan; Strecker, Tracy E.; Lopez, Ramona; Liu, Li; George, Clinton S.; Tanpure, Rajendra P.; Hamel, Ernest; Chaplin, David J.; Mason, Ralph P.; Trawick, Mary Lynn; Pinney, Kevin G. published their research in Bioorganic & Medicinal Chemistry on December 15 ,2015. The article was titled 《Structural interrogation of benzosuberene-based inhibitors of tubulin polymerization》.Related Products of 33797-34-1 The article contains the following contents:

The discovery of 3-methoxy-9-(3′,4′,5′-trimethoxyphenyl)-6,7-dihydro-5H-benzo[7]annulen-4-ol (a benzosuberene-based analog referred to as KGP18) was originally inspired by the natural products colchicine and combretastatin A-4 (CA4). The relative structural simplicity and ease of synthesis of KGP18, coupled with its potent biol. activity as an inhibitor of tubulin polymerization and its cytotoxicity (in vitro) against human cancer cell lines, has resulted in studies focused on new analog design and synthesis. The goal was to probe the relationship of structure to function in this class of anticancer agents. A series of twenty-two new benzosuberene-based analogs of KGP18 was designed and synthesized. These compounds vary in their methoxylation pattern and sep. incorporate trifluoromethyl groups around the pendant aryl ring for the evaluation of the effect of functional group modifications on the fused six-membered aromatic ring. In addition, the 8,9-saturated congener of KGP18 has been synthesized to assess the necessity of unsaturation at the carbon atom bearing the pendant aryl ring. Six of the mols. from this benzosuberene-series of compounds were active (IC50 < 5 μM) as inhibitors of tubulin polymerization while four analogs were comparable (IC50 approx. 1 μM) in their tubulin inhibitory activity to CA4 and KGP18. The potency of a bis-trifluoromethyl analog I and the unsaturated KGP18 derivative II as inhibitors of tubulin assembly along with their moderate cytotoxicity suggested the potential utility of these compounds as vascular disrupting agents (VDAs) to selectively target microvessels feeding tumors. Accordingly, water-soluble and DMSO-soluble phosphate prodrug salts of each were synthesized for preliminary in vivo studies to assess their potential efficacy as VDAs. In the part of experimental materials, we found many familiar compounds, such as (3-Methoxy-2-methylphenyl)methanol(cas: 33797-34-1Related Products of 33797-34-1)

(3-Methoxy-2-methylphenyl)methanol(cas: 33797-34-1) belongs to ethers.Ethers do have nonbonding electron pairs on their oxygen atoms, and they can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. Related Products of 33797-34-1 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.

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

In 2014,Angewandte Chemie, International Edition included an article by Wang, Fengyan; Liu, Zhang; Wang, Bing; Feng, Liheng; Liu, Libing; Lv, Fengting; Wang, Yilin; Wang, Shu. Safety of 1,4-Diethynyl-2,5-dimethoxybenzene. The article was titled 《Multi-Colored Fibers by Self-Assembly of DNA, Histone Proteins, and Cationic Conjugated Polymers》. The information in the text is summarized as follows:

The development of biomol. fiber materials with imaging ability has become more and more useful for biol. applications. Cationic conjugated polymers (CCPs) were used to construct inherent fluorescent microfibers with natural biol. macromols. (DNA and histone proteins) through the interfacial polyelectrolyte complexation (IPC) procedure. Isothermal titration microcalorimetry results show that the driving forces for fiber formation are electrostatic and hydrophobic interactions, as well as the release of counterions and bound water mols. Color-encoded IPC fibers were also obtained based on the co-assembly of DNA, histone proteins, and blue-, green-, or red- (RGB-) emissive CCPs by tuning the fluorescence resonance energy-transfer among the CCPs at a single excitation wavelength. The fibers could encapsulate GFP-coded Escherichia coli BL21, and the expression of GFP proteins was successfully regulated by the external environment of the fibers. These multi-colored fibers show a great potential in biomedical applications, such as biosensor, delivery, and release of biol. mols. and tissue engineering. The experimental process involved the reaction of 1,4-Diethynyl-2,5-dimethoxybenzene(cas: 74029-40-6Safety of 1,4-Diethynyl-2,5-dimethoxybenzene)

1,4-Diethynyl-2,5-dimethoxybenzene(cas: 74029-40-6) belongs to ethers.Ethers do have nonbonding electron pairs on their oxygen atoms, and they 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.Safety of 1,4-Diethynyl-2,5-dimethoxybenzene

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

In 2019,Angewandte Chemie, International Edition included an article by Pitts, Cody Ross; Bornemann, Dustin; Liebing, Phil; Santschi, Nico; Togni, Antonio. Quality Control of 1,2-Diphenyldisulfane. The article was titled 《Making the SF5 Group More Accessible: A Gas-Reagent-Free Approach to Aryl Tetrafluoro-λ6-sulfanyl Chlorides》. The information in the text is summarized as follows:

A series of aryl tetrafluoro-λ6-sulfanyl chlorides R-X [R = Ph, 4-BzOC6H4, 5-Br-2-pyridyl, 5-Br-2-pyrimidinyl, etc.; X = SF4Cl] was synthesized via trifluoroacetic acid catalyzed gas-reagent-free oxidative polyfluorination of aryl disulfides. This approach overcame the reliance on hazardous fluorinating reagents and/or gas reagents (e.g. Cl2) by employing easy-to-handle trichloroisocyanuric acid, potassium fluoride and catalytic amounts of acid. Furthermore, the same approach provided an access to compounds R-X [X = SF3, SF5, SeF3] which extended the applications of this chem. beyond arene SF5-functionalization and demonstrated its ability to address a more general oxidative fluorination problem. In the experiment, the researchers used many compounds, for example, 1,2-Diphenyldisulfane(cas: 882-33-7Quality Control of 1,2-Diphenyldisulfane)

1,2-Diphenyldisulfane(cas: 882-33-7) belongs to ethers.The C-O bonds that comprise simple ethers are strong. Quality Control of 1,2-Diphenyldisulfane They are unreactive toward all but the strongest bases. Although generally of low chemical reactivity, they are more reactive than alkanes.

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

In 2019,European Journal of Organic Chemistry included an article by Elinson, Michail N.; Vereshchagin, Anatoly N.; Anisina, Yuliya E.; Fakhrutdinov, Artem N.; Goloveshkin, Alexander S.; Egorov, Mikhail P.. Application of 673-22-3. The article was titled 《Pot-, Atom- and Step-Economic (PASE) Multicomponent Approach to the 5-(Dialkylphosphonate)-Substituted 2,4-Diamino-5H-chromeno[2,3-b]pyridine Scaffold》. The information in the text is summarized as follows:

A new multicomponent reaction is reported: the one-pot transformation of salicylaldehydes, 2-aminoprop-1-ene-1,1,3-tricarbonitrile (malononitrile dimer), and trialkylphosphites results in the efficient formation of (2,4-diamino-3-cyano-5H-chromeno[2,3-b]pyridin-5-yl)phosphonates. The scope of this one-pot reaction was investigated. The isolation of substituted phosphonates is very easy. The optimized reaction conditions and a mechanistic rationale for the complex multicomponent transformation are presented. This facile PASE approach offers a powerful tool for the selective formation of new types of functionalized 5-P-substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine scaffolds containing the phosphonate fragment, which are promising compounds for various biomedical applications, among them the treatment of human inflammatory diseases and cancer therapy. After reading the article, we found that the author used 2-Hydroxy-4-methoxybenzaldehyde(cas: 673-22-3Application of 673-22-3)

2-Hydroxy-4-methoxybenzaldehyde(cas: 673-22-3) is employed in the synthesis of Schiff base ligand. It is applied as a reactant in the synthesis of LPA1R antagonists used in the inhibition of LPA-induced proliferation and contraction of normal human lung fibroblasts. Also used in the synthesis of tyrosine kinase 6 proteinase inhibitors.Application of 673-22-3

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

《Chalcogen Bonding of SO2 and s-Block Metal Iodides Near Room Temperature: A Remarkable Structural Diversity》 was published in European Journal of Inorganic Chemistry in 2020. These research results belong to Dankert, Fabian; Feyh, Anne; von Haenisch, Carsten. Electric Literature of C10H20O5 The article mentions the following:

In this contribution the authors have systematically explored the coordination chem. of the iodide anion towards SO2. While employing large organocations like s-block metal complexes of crown-ethers, the authors discovered a remarkable structural diversity within the herein characterized compounds together with novel architectures of SO2 solvates. The observed O2S···I- interactions are strong enough to determine the crystal packing and dimensionality. In the light of chalcogen bonding, the small mol. SO2 is introduced as a supramol. synthon. In the light of a chem. in non-aqueous solutions, the ISO2- anion is revisited. Chalcogen bonding was established to form one-dimensional networks in the compounds [Li([12]crown-4)H2O]I·SO2 (1), [Na([15]crown-5)(SO2)I] (2), [K([18]crown-6)(SO2)I] (4), [NH4([18]crown-6)]I·SO2 (5), [Rb([18]crown-6)I(SO2)]·2SO2 (6) and [Cs([18]crown-6)(SO2)2I] (7) all of which were obtained by 1:1 complexation of the resp. iodide salt and resp. crown-ether in SO2 solution Two-dimensional networks were obtained within the alk. earth metal compounds [Mg([12]crown-4)2]I2·4SO2 (9) and [Ba2([18]crown-6)2(SO2I)(SO2)2I3]·SO2 (11). The iodosulfite ion ISO2- was obtained either by shielding Na+ ions with [12]crown-4, conversion of MgI2 with [15]crown-5, conversion of CaI2 with [18]crown-6 or conversion of BaI2 with [18]crown-6 (11, as aforementioned). [Na([12]crown-4)2]ISO2 (3), [Mg([15]crown-5)(ISO2)2] (8) and [Ca2([18]crown-6)(SO2I)3]I3 (10) were characterized. In these resp. compounds the S···I atom distances are considerably shorter than those previously reported. Exptl. data around the chem. of halosulfites is provided. Besides network structures and the iodosulfite formation, an SO2-rich aggregate could be observed An SO2 adduct of the composition [I2(SO2)5]2- is present in [Na([12]crown-4)2]I·2.75SO2 (3a). After reading the article, we found that the author used 1,4,7,10,13-Pentaoxacyclopentadecane(cas: 33100-27-5Electric Literature of C10H20O5)

1,4,7,10,13-Pentaoxacyclopentadecane(cas: 33100-27-5) is a member of crown ether Ligands. Crown-ethers are macrocyclic polyethers capable of forming host-guest complexes, especially with inorganic and organic cations. Crown-ethers can incorporate protonated primary amine compounds by formation of ion-dipole bonds with the oxygen atoms of the chiral selector. Crown-ethers have been widely used for the separation of several pharmaceuticals both in aqueous and non-aqueous media. Electric Literature of C10H20O5

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