Month: October 2022

Usutani, Hirotsugu; Cork, David G. published an article in Organic Process Research & Development. The title of the article was 《Effective Utilization of Flow Chemistry: Use of Unstable Intermediates, Inhibition of Side Reactions, and Scale-Up for Boronic Acid Synthesis》.Formula: C12H15BrO The author mentioned the following in the article:

Flow chem. processes for boronic acid syntheses utilizing lithiation-borylation have been developed. The side reactions in the lithiation step that occur in batch were suppressed, and unstable lithium intermediates were handled safely. Flow technol. was applied to several kinds of boronic acid syntheses, and scale-up was successfully conducted to allow kilogram-scale production Some of the key benefits of flow flash chem. were utilized, both to avoid side reactions and to enable dianion chem. that is difficult to perform successfully in batch reactions. The examples showed further perspectives on the utility of flow technologies for process development. In the experimental materials used by the author, we found 1-Bromo-4-(cyclohexyloxy)benzene(cas: 30752-31-9Formula: C12H15BrO)

1-Bromo-4-(cyclohexyloxy)benzene(cas: 30752-31-9) belongs to organobromine compounds.Most of the natural organobromine compounds are produced by marine organisms , and several brominated metabolites with antibacterial , antitumor , antiviral , and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. Formula: C12H15BrO In contrast, terrestrial plants account only for a few bromine-containing compounds.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2015,Schweighauser, Luca; Strauss, Marcel A.; Bellotto, Silvia; Wegner, Hermann A. published 《Attraction or Repulsion? London Dispersion Forces Control Azobenzene Switches》.Angewandte Chemie, International Edition published the findings.Recommanded Product: 3,5-Dibromoaniline The information in the text is summarized as follows:

Large substituents are commonly seen as entirely repulsive through steric hindrance. Such groups have addnl. attractive effects arising from weak London dispersion forces between the neutral atoms. Steric interactions are recognized to have a strong influence on isomerization processes, such as in azobenzene-based mol. switches. Textbooks indicate that steric hindrance destabilizes the Z isomers. Herein, increasing the bulkiness of electronically equal substituents in the meta-position decreases the thermal reaction rates from the Z to the E isomers. DFT computations revealed that attractive dispersion forces essentially lower the energy of the Z isomers. In the experimental materials used by the author, we found 3,5-Dibromoaniline(cas: 626-40-4Recommanded Product: 3,5-Dibromoaniline)

3,5-Dibromoaniline(cas: 626-40-4) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.Recommanded Product: 3,5-Dibromoaniline

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2019,European Journal of Pharmacology included an article by Wojcik-Pszczola, Katarzyna; Chlon-Rzepa, Grazyna; Jankowska, Agnieszka; Ellen, Eugenie; Swierczek, Artur; Pociecha, Krzysztof; Koczurkiewicz, Paulina; Piska, Kamil; Gawedzka, Anna; Wyska, Elzbieta; Knapik-Czajka, Malgorzata; Pekala, Elzbieta; Gosens, Reinoud. Safety of Ethyl 4-bromobutyrate. The article was titled 《Novel phosphodiesterases inhibitors from the group of purine-2,6-dione derivatives as potent modulators of airway smooth muscle cell remodelling》. The information in the text is summarized as follows:

Airway remodelling (AR) is an important pathol. feature of chronic asthma and chronic obstructive pulmonary disease. The etiol. of AR is complex and involves both lung structural and immune cells. One of the main contributors to airway remodelling is the airway smooth muscle (ASM), which is thickened by asthma, becomes more contractile and produces more extracellular matrix. As a second messenger, adenosine 3′,5′-cyclic monophosphate (cAMP) has been shown to contribute to ASM cell (ASMC) relaxation as well as to anti-remodelling effects in ASMC. Phosphodiesterase (PDE) inhibitors have drawn attention as an interesting new group of potential anti-inflammatory and anti-remodelling drugs. Recently, new hydrazide and amide purine-2,6-dione derivatives with anti-inflammatory properties have been synthesized by our team (compounds 1 and 2). The results show that both compounds have subtype specificity for several PDE isoforms (including inhibition of PDE1, PDE3, PDE4 and PDE7). Interestingly, such combined PDE subtype inhibition exerts improved anti-remodelling efficacies against several ASMC-induced responses such as proliferation, contractility, extracellular matrix (ECM) protein expression and migration when compared to other non-selective and selective PDE inhibitors. Our findings open novel perspectives in the search for new chem. entities with dual anti-inflammatory and anti-remodelling profiles in the group of purine-2,6-dione derivatives as broad-spectrum PDE inhibitors. The experimental part of the paper was very detailed, including the reaction process of Ethyl 4-bromobutyrate(cas: 2969-81-5Safety of Ethyl 4-bromobutyrate)

Ethyl 4-bromobutyrate(cas: 2969-81-5) 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.Safety of Ethyl 4-bromobutyrate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Cationic Co(I)-Intermediates for Hydrofunctionalization Reactions: Regio- and Enantioselective Cobalt-Catalyzed 1,2-Hydroboration of 1,3-Dienes》 were Duvvuri, Krishnaja; Dewese, Kendra R.; Parsutkar, Mahesh M.; Jing, Stanley M.; Mehta, Milauni M.; Gallucci, Judith C.; RajanBabu, T. V.. And the article was published in Journal of the American Chemical Society in 2019. Product Details of 1779-49-3 The author mentioned the following in the article:

Much of the recent work on catalytic hydroboration of alkenes has focused on simple alkenes and styrene derivatives with few examples of reactions of 1,3-dienes, which are reported to undergo mostly 1,4-additions to give allylic boronates. Reduced Co catalysts generated from 1,n-bis-diphenylphosphinoalkane complexes [Ph2P-(CH2)n-PPh2]CoX2; (n = 1-5) or from (2-oxazolinyl)phenyldiarylphosphine complexes [(G-PHOX)CoX2] (G = 4-substituent on oxazoline ring) effect selective 1,2-, 1,4-, or 4,3-additions of pinacolborane (HBPin) to a variety of 1,3-dienes depending on the ligands chosen. Conditions optimize the 1,2-additions The reactive catalysts can be generated from the Co(II)-complexes using trimethylaluminum, Me aluminoxane, or activated Zn in the presence of Na tetrakis[(3,5-trifluoromethyl)phenyl]borate (NaBARF). The complex, (dppp)CoCl2, gives the best results (ratio of 1,2- to 1,4-addition >95:5) for a variety of linear terminal 1,3-dienes and 2-substituted 1,3-dienes. The [(PHOX)CoX2] (X = Cl, Br) complexes give mostly 1,4-addition with linear unsubstituted 1,3-dienes, but, surprisingly, selective 1,2-additions with 2-substituted or 2,3-disubstituted 1,3-dienes. Isolated and fully characterized (x-ray crystallog.) Co(I)-complexes, (dppp)3Co2Cl2 and [(S,S)-BDPP]3Co2Cl2, do not catalyze the reaction unless activated by a Lewis acid or NaBARF, suggesting a key role for a cationic Co(I) species in the catalytic cycle. Regio- and enantioselective 1,2-hydroborations of 2-substituted 1,3-dienes are best accomplished using a catalyst prepared via activation of a chiral phosphinooxazoline-Co(II) complex with Zn and NaBARF. A number of common functional groups, among them, -OBn, -OTBS, -OTs, N-phthalimido- groups, are tolerated, and er’s > 95:5 were obtained for several dienes including 1-alkenylcycloalk-1-enes. This operationally simple reaction expands the realm of asym. hydroboration to provide direct access to a number of nearly enantiopure homoallylic boronates, which are not readily accessible by current methods. The resulting boronates were converted into the corresponding alcs., K trifluororoborate salts, N-BOC amines, and aryl derivatives by C-BPin to C-aryl transformation. The results came from multiple reactions, including the reaction of Methyltriphenylphosphonium bromide(cas: 1779-49-3Product Details of 1779-49-3)

Methyltriphenylphosphonium bromide(cas: 1779-49-3) is an organophosphorus compound, with potential use as a precursor and a solvent in organic synthesis. And it is used widely for methylenation via the Wittig reaction.Product Details of 1779-49-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Thermal behavior analysis as a valuable tool for comparing ionic liquids of different classes》 were Mezzetta, Andrea; Perillo, Vincenzo; Guazzelli, Lorenzo; Chiappe, Cinzia. And the article was published in Journal of Thermal Analysis and Calorimetry in 2019. Synthetic Route of C6H12Br2 The author mentioned the following in the article:

The thermal behavior of I [R = H, Br; X = Br, NTf2; n = 2, 6; m = 1, 4] and II ILs, belonging to two structurally related families with either bromide or Tf2N as counteranion, was analyzed. For bromide mono- I and dicationic ionic liquids II (DILs), thermal gravimetric anal. showed similar decomposition events, with only small gain in stability for a few members of the latter class. Conversely, all Tf2N DILs displayed higher stabilities (up to 34 K) than the corresponding monocations, thus highlighting the different role played by the two counteranions. Mono- and dicationic ILs bearing a reactive group on the imidazolium substituent resulted instead the least stable ILs studied. Differential scanning calorimetry anal. of most of the (D)ILs only showed glass transition temperatures, a behavior in agreement with the broad liquid range of ILs. The impact of the cationic structure and/or of the type of anion on the above-mentioned transition temperatures were studied. The apparent activation energy (Ea) and the fragility index (m) for some (D)ILs had also been obtained. Finally, a few bromide (D)ILs presented peculiar thermal events. In the experiment, the researchers used many compounds, for example, 1,6-Dibromohexane(cas: 629-03-8Synthetic Route of C6H12Br2)

1,6-Dibromohexane(cas: 629-03-8) is generally used to introduce C6 spacer in the molecular architecture. Some of the examples are: synthesis of solvent processable and conductive polyfluorene ionomers for alkaline fuel cell applications; synthesis of cross-linkable regioregular poly(3-(5-hexenyl)thiophene) (P3HNT) for stabilizing the film morphology in polymer photovoltaic cells.Synthetic Route of C6H12Br2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Synthesis and ring-opening metathesis polymerization of a new norbornene dicarboximide with a pendant carbazole moiety》 were Pragliola, Stefania; Botta, Antonio; Troiano, Rubina; Paradiso, Veronica; Grisi, Fabia. And the article was published in International Journal of Polymer Science in 2019. Recommanded Product: 623-24-5 The author mentioned the following in the article:

A new norbornene dicarboximide presenting a pendant carbazole moiety linked by a p-methylene benzyl spacer is synthesized. This carbazole-functionalized monomer is polymerized via ring-opening metathesis polymerization using Grubbs third-generation catalyst. Microstructural anal. of resulting polymers performed by NMR shows that they are stereoirregular. Wide-angle X-ray diffraction (WAXD) and thermal (DSC) anal. indicate that polymers are also amorphous. With respect to the fluorescence anal., both solution and film polymer samples exhibit only “”normal structured”” carbazole fluorescence, while excimer formation by overlap of carbazole groups is not detected. In the experiment, the researchers used many compounds, for example, 1,4-Bis(bromomethyl)benzene(cas: 623-24-5Recommanded Product: 623-24-5)

1,4-Bis(bromomethyl)benzene(cas: 623-24-5) belongs to organobromine compounds.Most of the natural organobromine compounds are produced by marine organisms , and several brominated metabolites with antibacterial , antitumor , antiviral , and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. Moreover, several studies demonstrate that the average proportion of bromine in drugs is significantly higher than that in natural products. Recommanded Product: 623-24-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Multikilogram Synthesis of a Potent Dual Bcl-2/Bcl-xL Antagonist. 2. Manufacture of the 1,3-Diamine Moiety and Improvement of the Final Coupling Reaction》 was published in Organic Process Research & Development in 2020. These research results belong to Hardouin, Christophe; Baillard, Sandrine; Bariere, Francois; Craquelin, Anthony; Grandjean, Mathieu; Janvier, Solenn; Le Roux, Stephane; Penloup, Christine; Russo, Olivier. Computed Properties of C4H7BrO2 The article mentions the following:

This paper describes the synthesis of kilogram quantities of the sulfonamide moiety I involved in a coupling reaction with acid moiety II to provide batches of drug candidate III for preclin. studies and first-in-human clin. trials. A first approach relying on a chiral separation furnished the desired enantiomer of 1,3-diamine IV, precursor of sulfonamide I. An enantiomeric synthesis of IV using the Ellman’s chiral auxiliary coupled with an aza-Reformatsky reaction to control the stereochem. is also discussed. Coupling conditions of the final step involving EDCI to provide III under a cGMP process are detailed. An alternative approach using N-(1-methanesulfonyl)benzotriazole is also presented. In the experimental materials used by the author, we found 4-Bromobutanoic acid(cas: 2623-87-2Computed Properties of C4H7BrO2)

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.).Computed Properties of C4H7BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Long-Lived Charge-Transfer State from B-N Frustrated Lewis Pairs Enchained in Supramolecular Copolymers》 was published in Journal of the American Chemical Society in 2020. These research results belong to Adelizzi, Beatrice; Chidchob, Pongphak; Tanaka, Naoki; Lamers, Brigitte A. G.; Meskers, Stefan C. J.; Ogi, Soichiro; Palmans, Anja R. A.; Yamaguchi, Shigehiro; Meijer, E. W.. Quality Control of Tris(4-bromophenyl)amine The article mentions the following:

The field of supramol. polymers is rapidly expanding; however, the exploitation of these systems as functional materials is still elusive. To become competitive, supramol. polymers must display microstructural order and the emergence of new properties upon copolymerization To tackle this, a greater understanding of the relationship between monomers’ design and polymer microstructure is required as well as a set of functional monomers that efficiently interact with one another to synergistically generate new properties upon copolymerization Here, we present the first implementation of frustrated Lewis pairs into supramol. copolymers. Two supramol. copolymers based on π-conjugated O-bridged triphenylborane and two different triphenylamines display the formation of B-N pairs within the supramol. chain. The remarkably long lifetime and the circularly polarized nature of the resulting photoluminescence emission highlight the possibility to obtain an intermol. B-N charge transfer. These results are proposed to be the consequences of the enchainment of B-N frustrated Lewis pairs within 1D supramol. aggregates. Although it is challenging to obtain a precise mol. picture of the copolymer microstructure, the formation of random blocklike copolymers could be deduced from a combination of optical spectroscopic techniques and theor. simulation. In the part of experimental materials, we found many familiar compounds, such as Tris(4-bromophenyl)amine(cas: 4316-58-9Quality Control of Tris(4-bromophenyl)amine)

In other references, Tris(4-bromophenyl)amine(cas: 4316-58-9) is often used in the synthesis of porous luminescent covalent–organic polymers (COPs)Quality Control of Tris(4-bromophenyl)amine

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Ligand-Controlled Product Selectivity in Electrochemical Carbon Dioxide Reduction Using Manganese Bipyridine Catalysts》 was written by Roenne, Magnus H.; Cho, Dasol; Madsen, Monica R.; Jakobsen, Joakim B.; Eom, Seunghwan; Escoude, Emile; Hammershoej, Hans Christian D.; Nielsen, Dennis U.; Pedersen, Steen U.; Baik, Mu-Hyun; Skrydstrup, Troels; Daasbjerg, Kim. Recommanded Product: Bromopentacarbonylmanganese(I) And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

Electrocatalysis is a promising tool for using CO2 as a feedstock in the chem. industry. However, controlling the selectivity for different CO2 reduction products remains a major challenge. The authors report Mn carbonyl complexes with elaborated bipyridine or phenanthroline ligands that can reduce CO2 to either formic acid, if the ligand structure contains strategically positioned tertiary amines, or CO, if the amine groups are absent in the ligand or are placed far from the metal center. The amine-modified complexes are benchmarked to be among the most active catalysts for reducing CO2 to formic acid, with a maximum turnover frequency of up to 5500 s-1 at an overpotential of 630 mV. The conversion even works at overpotentials ≥300 mV, although through an alternative mechanism. Mechanistically, the formation of a Mn-hydride species aided by in situ protonated amine groups is a key intermediate by cyclic voltammetry, 1H NMR, DFT calculations, and IR spectroelectrochem. The experimental part of the paper was very detailed, including the reaction process of Bromopentacarbonylmanganese(I)(cas: 14516-54-2Recommanded Product: Bromopentacarbonylmanganese(I))

Bromopentacarbonylmanganese(I)(cas: 14516-54-2) has many other uses. It is used in the formation of (eta6-arene)tricarbonylmanganese(I) by reacting with arene (arene= hexamethyl benzene, 1,2,4,5-tetramethyl benzene, mesitylene, p-xylene and toluene) in the presence silver salt.Recommanded Product: Bromopentacarbonylmanganese(I)

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Development, synthesis and biological investigation of a novel class of potent PC-PLC inhibitors》 was written by Pilkington, Lisa I.; Sparrow, Kevin; Rees, Shaun W. P.; Paulin, Emily K.; van Rensburg, Michelle; Xu, Chris Sun; Langley, Ries J.; Leung, Ivanhoe K. H.; Reynisson, Johannes; Leung, Euphemia; Barker, David. Recommanded Product: o-Bromobenzaldehyde And the article was included in European Journal of Medicinal Chemistry in 2020. The article conveys some information:

Phospholipases are enzymes that are involved in the hydrolysis of acyl and phosphate esters of phospholipids, generating secondary messengers that have implications in various cellular processes including proliferation, differentiation and motility. As such inhibitors of phospholipases have been widely studied for their use as anti-cancer therapeutics. Phosphatidylcholine-specific phospholipase C (PC-PLC) is implicated in the progression of a number of cancer cell lines including aggressing triple-neg. breast cancers. Most current studies on PC-PLC have utilized D609 as the standard inhibitor however it is known to have multiple failings, including poor stability in aqueous media. 2-Morpholinobenzoic acids were recently identified using vHTS as a potential class of lead compounds, with improvements over D609. In this work 129 analogs in this class were prepared and their PC-PLC inhibitory activity was assessed. It was found that the majority of these novel compounds had improved activity when compared to D609 with the most potent inhibitors completely inhibiting enzyme activity. It was determined that the best compound/s contained a morpholino and 2-substituted N-benzyl moieties with these findings explained using mol. modeling. The compounds reported here will allow for improved study of PC-PLC activity. After reading the article, we found that the author used o-Bromobenzaldehyde(cas: 6630-33-7Recommanded Product: o-Bromobenzaldehyde)

o-Bromobenzaldehyde(cas: 6630-33-7) is used in L-threonine aldolase-catalyzed enantio/diastereoselective aldol reactions.Recommanded Product: o-BromobenzaldehydeSynthetic 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