Month: October 2022

Tien, Chieh-Hung; Trofimova, Alina; Holownia, Aleksandra; Kwak, Branden S.; Larson, Reed T.; Yudin, Andrei K. published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Carboxyboronate as a Versatile In Situ CO Surrogate in Palladium-Catalyzed Carbonylative Transformations》.Formula: C7H5BrO2 The article contains the following contents:

The application of carboxy-MIDA-boronate (MIDA=N-methyliminodiacetic acid) as an in situ CO surrogate for various palladium-catalyzed transformations is described. Carboxy-MIDA-boronate was previously shown to be a bench-stable boron-containing building block for the synthesis of borylated heterocycles. The present study demonstrates that, in addition to its utility as a precursor to heterocycle synthesis, carboxy-MIDA-boronate is an excellent in situ CO surrogate that is tolerant of reactive functionalities such as amines, alcs., and carbon-based nucleophiles. Its wide functional-group compatibility is highlighted in the palladium-catalyzed aminocarbonylation, alkoxycarbonylation, carbonylative Sonogashira coupling, and carbonylative Suzuki-Miyaura coupling of aryl halides. A variety of amides, esters, (hetero)aromatic ynones, and bis(hetero)aryl ketones were synthesized in good-to-excellent yields in a one-pot fashion. The experimental part of the paper was very detailed, including the reaction process of 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4Formula: C7H5BrO2)

Furthermore, the coupling of 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4) with β-methallyl alcohol was catalyzed by Pd(OAc)2 in combination with P(t-Bu)3.Formula: C7H5BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhang, Mingming; Wei, Wei; Peng, Chengjun; Ma, Xiaodong; He, Xiao; Zhang, Heng; Zhou, Mingkang published their research in Bioorganic & Medicinal Chemistry Letters in 2021. The article was titled 《Discovery of novel pyrazolopyrimidine derivatives as potent mTOR/HDAC bi-functional inhibitors via pharmacophore-merging strategy》.Category: bromides-buliding-blocks The article contains the following contents:

The mTOR and HDAC dual suppression is meaningful for counteracting drug resistance resulted from kinase mutation and bypass mechanisms. Herein, we communicate our recent discovery of a novel structural series of mTOR/HDAC bi-functional inhibitors featuring the pyrazolopyrimidine core via pharmacophore-merging strategy. More than half of them exerted potent dual-target inhibitory activities. In particular, compound 50 exhibited IC50 values of 0.49 and 0.91 nM against mTOR and HDAC1, resp., along with remarkably enhanced anti-proliferative activity (IC50 = 1.74μM) against MV4-11 cell line than mTOR inhibitor MLN-0128 (IC50 = 5.84μM) and HDAC inhibitor SAHA (IC50 = 8.44μM). Its intracellular intervention of both mTOR signaling and HDAC was validated by the Western blot anal. Moreover, as the first disclosed mTOR/HDAC dual inhibitor with selectivity for some specific HDAC subtypes, it has the potential to alleviate the adverse effects resulted from pan-HDAC inhibition. Attributed to its favorable in vitro performance, compound 50 is valuable for further functional investigation as a polypharmacol. anti-cancer agent. The experimental process involved the reaction of Ethyl 5-bromovalerate(cas: 14660-52-7Category: bromides-buliding-blocks)

Ethyl 5-bromovalerate(cas: 14660-52-7) belongs to bromides. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhang, Zhongchao; Chen, Sijia; Tang, Fu; Guo, Kai; Liang, Xin-Ting; Huang, Jun; Yang, Zhen published their research in Journal of the American Chemical Society in 2021. The article was titled 《Total Synthesis of (+)-Cyclobutastellettolide B》.Quality Control of Ethyltriphenylphosphonium bromide The article contains the following contents:

A convenient enantioselective total synthesis of (+)-cyclobutastellettolide B (I) via a strategy that involves a diastereoselective Johnson-Claisen rearrangement, a regioselective cyclopropoxytrimethylsilane ring-opening reaction, and a Norrish-Yang cyclization is described. The results of computational and exptl. studies indicate that the regio- and stereoselectivity of the Norrish-Yang reaction are controlled by the C-H bond dissociation energy and restricted rotation of the C13-C14 bond. In the experiment, the researchers used many compounds, for example, Ethyltriphenylphosphonium bromide(cas: 1530-32-1Quality Control of Ethyltriphenylphosphonium bromide)

Ethyltriphenylphosphonium bromide(cas: 1530-32-1) is a phase transfer catalyst, used to accelerate the cure of phenolic-based epoxy resins, certain fluoroelastomer resins and thermosetting powder coatings. It is also used as catalysts in the synthesis of certain organic compounds and as a pharmaceutical intermediate.Quality Control of Ethyltriphenylphosphonium bromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Fernandes, Debora da S. M.; Lago, Aline de F. S.; Thomasi, Sergio S.; Freitas, Matheus P. published an article in 2021. The article was titled 《Conformational analysis of halobenzaldehydes: A theoretical and spectroscopic study》, and you may find the article in Journal of Molecular Structure.HPLC of Formula: 6630-33-7 The information in the text is summarized as follows:

Rotation of the formyl group in halobenzaldehydes (halo = F, Cl, and Br) has been studied through high-level d. functional theory (DFT) calculations and natural bond orbital (NBO) anal. The isomeric and conformational energies are dictated by non-Lewis and Lewis-type interactions. The 4-substituted benzaldehydes the most stable isomer due especially to an effective electron resonance and small dipole moment, while destabilizing Lewis-type interactions slightly override the non-Lewis electron delocalization both in the syn and anti conformers of meta isomer. No significant halogen effect is observed on stabilities, excepting for the least stable ortho isomer, where the halogen interacts with the formyl group. Such interaction is more repulsive in the syn conformer (where the halogen and oxygen atoms face one another), but the nature of this interaction changes from predominantly electrostatic to steric contribution on going from F to Br. IR stretching vibrations, as well as NMR chem. shifts and spin-spin coupling constants, provided valuable insight into through-bond and through-space effects influencing the stabilities of these compounds In the part of experimental materials, we found many familiar compounds, such as o-Bromobenzaldehyde(cas: 6630-33-7HPLC of Formula: 6630-33-7)

o-Bromobenzaldehyde(cas: 6630-33-7) is used in L-threonine aldolase-catalyzed enantio/diastereoselective aldol reactions.HPLC of Formula: 6630-33-7Synthetic applications of o-Bromobenzaldehyde include: synthesis of aza-fused polycyclic quinolines through copper-catalyzed cascade reaction, preparation of 1-substituted indazoles by CuI-catalyzed coupling with N-aryl hydrazides.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Herrera-Luna, Jorge C.; Diaz, David Diaz; Jimenez, M. Consuelo; Perez-Ruiz, Raul published an article in 2021. The article was titled 《Highly Efficient Production of Heteroarene Phosphonates by Dichromatic Photoredox Catalysis》, and you may find the article in ACS Applied Materials & Interfaces.SDS of cas: 3141-27-3 The information in the text is summarized as follows:

A new strategy to achieve efficient aerobic phosphorylation of five-membered heteraroenes with excellent yields using dichromatic photoredox catalysis in a gel-based nanoreactor is described here. The procedure involves visible aerobic irradiation (cold white LEDs) of a mixture containing the heteroarene halide, trisubstituted phosphite, N,N-diisopropylethylamine (DIPEA) as sacrificial agent, and catalytic amounts of 9,10-dicyanoanthracene (DCA) in the presence of an adequate gelator, which permits a faster process than at the homogeneous phase. The methodol., which operates by a consecutive photoinduced electron transfer (ConPET) mechanism, was successfully applied to the straightforward and clean synthesis of a number of different heteroarene (furan, thiophene, selenophene, pyrrole, oxazole, or thioxazole) phosphonates, extending to the late-stage phosphonylation of the anticoagulant rivaroxaban. Strategically, employment of cold white light is critical since it provides both selective wavelengths for exciting 1st DCA (blue region) and subsequently its corresponding radical anion DCA•- (green region). The resultant strongly reducing excited agent DCA•-* is capable of even activate five-membered heteroarene halides (Br, Cl) with high reduction potentials (~-2.7 V) to effect the C(sp2)-P bond formation. Spectroscopic and thermodn. studies have supported the proposed reaction mechanism. The rate of product formation was clearly enhanced in gel media because reactants can be presumably localized not only in the solvent pools but also through to the fibers of the viscoelastic gel network. This was confirmed by field-emission SEM images where a marked densification of the network was observed, modifying its fibrillary morphol. Finally, rheol. measurements showed the resistance of the gel network to the incorporation of the reactants and the formation of the desired products. In the part of experimental materials, we found many familiar compounds, such as 2,5-Dibromothiophene(cas: 3141-27-3SDS of cas: 3141-27-3)

2,5-Dibromothiophene(cas: 3141-27-3) , is mainly used as pharmaceutical intermediate and synthesis intermediate. 2,5-Dibromothiophene may be used as starting reagent for the synthesis of α,α′-didecylquater-, -quinque- and -sexi-thiophenes.SDS of cas: 3141-27-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Murphy, Manoharan; Theyagarajan, K.; Thenmozhi, Kathavarayan; Senthilkumar, Sellappan published an article in 2021. The article was titled 《Direct electrochemistry of covalently immobilized hemoglobin on a naphthylimidazolium butyric acid ionic liquid/MWCNT matrix》, and you may find the article in Colloids and Surfaces, B: Biointerfaces.Application of 2623-87-2 The information in the text is summarized as follows:

Monitoring the concentration levels of hydrogen peroxide (H2O2) is significant in both clin. and industrial applications. Herein, we develop a facile biosensor for the detection of H2O2 based on direct electron transfer of Hb (Hb), which was covalently immobilized on a hydrophobic naphthylimidazolium butyric acid ionic liquid (NIBA-IL) over a multiwalled carbon nanotube (MWCNT) modified glassy carbon electrode (GCE) to obtain an Hb/NIBA-IL/MWCNT/GCE. Highly water-soluble Hb protein was firmly immobilized on NIBA-IL via stable amide bonding between the free -NH2 groups of Hb and -COOH groups of NIBA-IL via EDC/NHS coupling. Thus fabricated biosensor showed a well resolved redox peak with a cathodic peak potential (Epc) at -0.35 V and anodic peak potential (Epa) at -0.29 V with a formal potential (E°’) of -0.32 V, which corresponds to the deeply buried FeIII/FeII redox center of Hb, thereby direct electrochem. of Hb was established. Further, the modified electrode demonstrated very good electrocatalytic activity towards H2O2 reduction and showed a wide linear range of detection from 0.01 to 6.3 mM with a limit of detection and sensitivity of 3.2μM and 111μA mM-1 cm-2, resp. Moreover, the developed biosensor displayed high operational stability under dynamic conditions as well as during continuous potential cycles and showed reliable reproducibility. The superior performance of the fabricated biosensor is attributed to the effective covalent immobilization of Hb on the newly developed highly conducting and biocompatible NIBA-IL/MWCNT/GCE platform. In the experimental materials used by the author, we found 4-Bromobutanoic acid(cas: 2623-87-2Application of 2623-87-2)

4-Bromobutanoic acid(cas: 2623-87-2) belongs to carboxylic acids. The chief chemical characteristic of the carboxylic acids is their acidity. They are generally more acidic than other organic compounds containing hydroxyl groups but are generally weaker than the familiar mineral acids (e.g., hydrochloric acid, HCl, sulfuric acid, H2SO4, etc.).Application of 2623-87-2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Heinen, Flemming; Reinhard, Dominik L.; Engelage, Elric; Huber, Stefan M. published an article in 2021. The article was titled 《A bidentate iodine(III)-based halogen-bond donor as a powerful organocatalyst》, and you may find the article in Angewandte Chemie, International Edition.Recommanded Product: 2,5-Dibromothiophene The information in the text is summarized as follows:

In contrast to iodine(I)-based halogen bond donors, iodine(III)-derived ones have only been used as Lewis acidic organocatalysts in a handful of examples, and in all cases they acted in a monodentate fashion. Herein, we report the first application of a bidentate bis(iodolium) salt as organocatalyst in a Michael and a nitro-Michael addition reaction as well as in a Diels-Alder reaction that had not been activated by noncovalent organocatalysts before. In all cases, the performance of this bidentate XB donor distinctly surpassed the one of arguably the currently strongest iodine(I)-based organocatalyst. Bidentate coordination to the substrate was corroborated by a structural anal. and by DFT calculations of the transition states. Overall, the catalytic activity of the bis(iodolium) system approaches that of strong Lewis acids like BF3. In the experiment, the researchers used many compounds, for example, 2,5-Dibromothiophene(cas: 3141-27-3Recommanded Product: 2,5-Dibromothiophene)

2,5-Dibromothiophene(cas: 3141-27-3) , is mainly used as pharmaceutical intermediate and synthesis intermediate. 2,5-Dibromothiophene may be used as starting reagent for the synthesis of α,α′-didecylquater-, -quinque- and -sexi-thiophenes.Recommanded Product: 2,5-Dibromothiophene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Takahashi, Yusuke; Seki, Masahiko published an article in 2021. The article was titled 《Finkelstein Reaction in Non-polar Organic Solvents: A Streamlined Synthesis of Organic Iodides》, and you may find the article in Organic Process Research & Development.Electric Literature of C7H13BrO2 The information in the text is summarized as follows:

The Finkelstein reaction of organic halides was found to proceed smoothly in non-polar organic solvents other than acetone when operated in the presence of a catalytic amount of tetra-n-butylammonium bromide and water. The new protocol was successfully applied to a preparation of Et 5-iodopentanoate from the corresponding bromide which was used directly for zinc reagent formation and Fukuyama coupling to enable the formation of the (+)-biotin side chain in a streamlined manner. Rate acceleration by microwave irradiation and an application to the synthesis of trimethylsilyl iodide was described as well. In the experiment, the researchers used Ethyl 5-bromovalerate(cas: 14660-52-7Electric Literature of C7H13BrO2)

Ethyl 5-bromovalerate(cas: 14660-52-7) belongs to bromides. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact.Electric Literature of C7H13BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tomasic, Tihomir; Rabbani, Said; Jakob, Roman P.; Reisner, Andreas; Jakopin, Ziga; Maier, Timm; Ernst, Beat; Anderluh, Marko published an article in 2021. The article was titled 《Does targeting Arg98 of FimH lead to high affinity antagonists?》, and you may find the article in European Journal of Medicinal Chemistry.Product Details of 14660-52-7 The information in the text is summarized as follows:

Bacterial resistance has become an important challenge in the treatment of urinary tract infections. The underlying resistance mechanisms can most likely be circumvented with an antiadhesive approach, antagonizing the lectin FimH located at the tip of fimbriae of uropathogenic E. coli. Here we report on a novel series of FimH antagonists based on the 1-(α-D-mannopyranosyl)-4-phenyl-1,2,3-triazole scaffold, designed to incorporate carboxylic acid or ester functions to interact with FimH Arg98. The most potent representative of the series, ester I, displayed a Kd value of 7.6 nM for the lectin domain of FimH with a general conclusion that all esters outperform carboxylates in terms of affinity. Surprisingly, all compounds from this new series exhibited improved binding affinities also for the R98A mutant, indicating another possible interaction contributing to binding. Our study on 1-(α-D-mannopyranosyl)-4-phenyl-1,2,3-triazole-based FimH antagonists offers proof that targeting Arg98 side chain by a “”chem. common sense””, i.e. by introduction of the acidic moiety to form ionic bond with Arg98 is most likely unsuitable approach to boost FimH antagonists’ potency. After reading the article, we found that the author used Ethyl 5-bromovalerate(cas: 14660-52-7Product Details of 14660-52-7)

Ethyl 5-bromovalerate(cas: 14660-52-7) belongs to bromides. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact.Product Details of 14660-52-7

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Dilauro, Giuseppe; Azzollini, Claudia S.; Vitale, Paola; Salomone, Antonio; Perna, Filippo M.; Capriati, Vito published an article in 2021. The article was titled 《Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands》, and you may find the article in Angewandte Chemie, International Edition.Computed Properties of C7H5BrO2 The information in the text is summarized as follows:

Pd-catalyzed Negishi cross-coupling reactions between organozinc compounds and (hetero)aryl bromides have been reported when using bulk water as the reaction medium in the presence of NaCl or the biodegradable choline chloride/urea eutectic mixture Both C(sp3)-C(sp2) and C(sp2)-C(sp2) couplings have been found to proceed smoothly, with high chemoselectivity, under mild conditions (room temperature or 60°C) in air, and in competition with protonolysis. Addnl. benefits include very short reaction times (20 s), good to excellent yields (up to 98%), wide substrate scope, and the tolerance of a variety of functional groups. The proposed novel protocol is scalable, and the practicability of the method is further highlighted by an easy recycling of both the catalyst and the eutectic mixture or water. The experimental process involved the reaction of 4-Bromobenzoic acid(cas: 586-76-5Computed Properties of C7H5BrO2)

4-Bromobenzoic acid(cas: 586-76-5) has been used to study the metabolic fate of 2-,3-and 4-bromo benzoic acids in rat hepatocytes incubation using high temperature liquid chromatography. It was used in bromine-specific detection of the metabolites of 2-,3-and 4-bromobenzoic acid in the urine and bile of rats by inductively coupled plasma mass spectrometry.Computed Properties of C7H5BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary