Category: bromides-buliding-blocks

《anti-Carbometalation of Alkynyl Sulfides Using Indium Tribromide and Ketene Silyl Acetals》 was published in Chemistry Letters in 2020. These research results belong to Kang, Kyoungmin; Sakamoto, Kosuke; Nishimoto, Yoshihiro; Yasuda, Makoto. Category: bromides-buliding-blocks The article mentions the following:

Regioselective anti-carbometalation of alkynyl sulfides via the use of InBr3 and organosilicon nucleophiles to give β-mercaptoalkenylindium compounds was developed. The structure of β-mercaptoalkenylindium was characterized by X-ray crystallog. anal. A variety of disubstituted alkenyl sulfides were regio- and stereoselectively obtained by either halogenation or Pd-catalyzed cross-coupling with aryl halides using the mercaptoalkenylindiums. In the experimental materials used by the author, we found Indium(III) bromide(cas: 13465-09-3Category: bromides-buliding-blocks)

Indium(III) bromide(cas: 13465-09-3) is used in organic synthesis as a water tolerant Lewis acid. It efficiently catalyzes the three-component coupling of β-keto esters, aldehydes and urea (or thiourea) to afford the corresponding dihydropyrimidinones.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Hydrosilylation of Esters Catalyzed by Bisphosphine Manganese(I) Complex: Selective Transformation of Esters to Alcohols》 was published in Organic Letters in 2020. These research results belong to Behera, Rakesh R.; Ghosh, Rahul; Panda, Surajit; Khamari, Subrat; Bagh, Bidraha. Safety of Bromopentacarbonylmanganese(I) The article mentions the following:

A tricarbonylruthenium Xantphos complex I was prepared and characterized by X-ray crystallog.; in the presence of I, esters underwent chemoselective hydrosilylation with phenylsilane under neat conditions (followed by workup with base) to yield esters. Aryl, alkyl, and alkenyl mono- and dicarboxylates and lactones underwent chemoselective reduction to alcs. and diols; ketoesters underwent reduction to diols. Poly(1,6-hexanediol adipate) underwent hydrosilylation to 1,6-hexanediol. The experimental process involved the reaction of Bromopentacarbonylmanganese(I)(cas: 14516-54-2Safety of 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.Safety of Bromopentacarbonylmanganese(I)

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Sustainable strategies based on glycine-betaine analogue ionic liquids for the recovery of monoclonal antibodies from cell culture supernatants》 were Capela, Emanuel V.; Santiago, Alexandre E.; Rufino, Ana F. C. S.; Tavares, Ana P. M.; Pereira, Matheus M.; Mohamadou, Aminou; Aires-Barros, M. Raquel; Coutinho, Joao A. P.; Azevedo, Ana M.; Freire, Mara G.. And the article was published in Green Chemistry in 2019. Product Details of 2969-81-5 The author mentioned the following in the article:

Monoclonal antibodies (mAbs) are of crucial interest for therapeutic purposes, particularly in vaccination and immunization, and in the treatment of life-threatening diseases. However, their downstream processing from the complex cell culture media in which they are produced still requires multiple steps, making mAbs extremely high-cost products. Therefore, the development of cost-effective, sustainable and biocompatible purification strategies for mAbs is in high demand to decrease the associated economic, environmental and health burdens. Herein, novel aqueous biphasic systems (ABS) composed of glycine-betaine analog ionic liquids (AGB-ILs) and K2HPO4/KH2PO4 at pH 7.0, the resp. three-phase partitioning (TPP) systems, and hybrid processes combined with ultrafiltration were investigated and compared in terms of performance as alternative strategies for the purification and recovery of anti-human interleukin-8 (anti-IL-8) mAbs, which are specific therapeutics in the treatment of inflammatory diseases, from Chinese Hamster Ovary (CHO) cell culture supernatants. With the studied ABS, mAbs preferentially partition to the IL-rich phase, with recovery yields up to 100% and purification factors up to 1.6. The best systems were optimized in what concerns the IL concentration, allowing to take advantage of IL-based three-phase partitioning approaches where a precipitate enriched in mAbs is obtained at the ABS interface, yielding 41.0% of IgG with a purification factor of 2.7 (purity of 60.9%). Hybrid processes combining the two previous techniques and an ultrafiltration step were finally applied, allowing the recovery of mAbs from the different fractions in an appropriate buffer solution for further biopharmaceutical formulations, while allowing the simultaneous IL removal and reuse. The best results were obtained with the hybrid process combining TPP and ultrafiltration, allowing to obtain mAbs with a purity higher than 60%. The recyclability of the IL was addnl. demonstrated, revealing no losses in the purification and recovery performance of these systems for mAbs. The biol. activity of anti-IL-8 mAbs is maintained after the several purification and recovery steps, indicating that the novel ABS, three-phase partitioning and hybrid processes comprising AGB-ILs are promising and sustainable strategies in mAbs downstream processing. The experimental process involved the reaction of Ethyl 4-bromobutyrate(cas: 2969-81-5Product Details of 2969-81-5)

Ethyl 4-bromobutyrate(cas: 2969-81-5) 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 2969-81-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《A laser driven flow chemistry platform for scaling photochemical reactions with visible light》 were Harper, Kaid C.; Moschetta, Eric G.; Bordawekar, Shailendra V.; Wittenberger, Steven J.. And the article was published in ACS Central Science in 2019. Synthetic Route of C7H4BrF3 The author mentioned the following in the article:

Visible-light-promoted organic reactions can offer increased reactivity and selectivity via unique reaction pathways to address a multitude of practical synthetic problems, yet few practical solutions exist to employ these reactions for multikilogram production We have developed a simple and versatile continuous stirred tank reactor (CSTR) equipped with a high-intensity laser to drive photochem. reactions at unprecedented rates in continuous flow, achieving kg/day throughput using a 100 mL reactor. Our approach to flow reactor design uses the Beer-Lambert law as a guideline to optimize catalyst concentration and reactor depth for maximum throughput. This laser CSTR platform coupled with the rationale for design can be applied to a breadth of photochem. reactions. The experimental process involved the reaction of 1-Bromo-4-(trifluoromethyl)benzene(cas: 402-43-7Synthetic Route of C7H4BrF3)

1-Bromo-4-(trifluoromethyl)benzene(cas: 402-43-7) belongs to organobromine compounds.The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides.Synthetic Route of C7H4BrF3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Hydrophilic quaternary ammonium-group-containing [FeFe]H2ase models prepared by quaternization of the pyridyl N atoms in pyridylazadiphosphine- and pyridylmethylazadiphosphine-bridged diiron complexes with various electrophiles》 were Song, Li-Cheng; Feng, Li; Guo, Yuan-Qiang. And the article was published in Dalton Transactions in 2019. Recommanded Product: 4-Bromobutanoic acid The author mentioned the following in the article:

The first aromatic quaternary ammonium-group-containing [FeFe]H2ase models have been prepared by a simple and convenient two-step method in high yields. Thus, on the basis of preparation of the N-pyridylazadiphosphine-bridged diiron complex (μ-PDT)Fe2(CO)4[μ-3-(Ph2P)2NC5H4N] (A) by CO substitution of parent complex (μ-PDT)Fe2(CO)6 with N-pyridylazadiphosphine 3-(Ph2P)2NC5H4N in refluxing xylene, further quaternization of the pyridyl N atom in complex A with electrophile 1,3-propanesultone, 1,3,2-dioxathiolane-2,2-dioxide, or 4-bromobutyric acid in refluxing MeCN afforded the pyridyl quaternary ammonium-group-containing models (μ-PDT)Fe2(CO)4[μ-3-(Ph2P)2NC5H4NR] (1, R = (CH2)3SO3; 2, R = (CH2)2OSO3) and (μ-PDT)Fe2(CO)4[μ-3-(Ph2P)2NC5H4N(CH2)3CO2H]Br (3). Similarly, the N-pyridylmethylazadiphosphine-bridged diiron complex (μ-PDT)Fe2(CO)4[μ-3-(Ph2P)2NCH2C5H4N] (B) could be prepared by CO substitution of parent complex (μ-PDT)Fe2(CO)6 with N-pyridylmethylazadiphosphine 3-(Ph2P)2NCH2C5H4N in refluxing xylene, while further quaternization of the pyridylmethyl N atom in complex B with 1,3-propanesultone and 3-bromo-1-propanol in MeCN at reflux gave the pyridylmethyl quaternary ammonium-group-containing models (μ-PDT)Fe2(CO)4[μ-3-(Ph2P)2NCH2C5H4N(CH2)3SO3] (4) and (μ-PDT)Fe2(CO)4[μ-3-(Ph2P)2NCH2C5H4N(CH2)3OH]Br (5), resp. All new complexes A, B, and 1-5 were characterized by elemental anal. and various spectroscopies, while the mol. structures of complexes A, B, 2 and 5 were further confirmed by x-ray crystallog. The electrochem. study on hydrophilic models 1 and 3 in MeCN and the MeCN/H2O mixed solvent indicated that the reduction potentials were shifted to less-neg. potentials as the water content increased; such an observation implies that both 1 and 3 are easily reduced in the mixed MeCN/H2O solvent than in MeCN. In addition, the electrocatalytic study demonstrated that both 1 and 3 can serve as electrocatalysts for H2 production from acetic acid with higher icat/ip and TONs in MeCN/H2O than in MeCN. In the experiment, the researchers used 4-Bromobutanoic acid(cas: 2623-87-2Recommanded Product: 4-Bromobutanoic acid)

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.).Recommanded Product: 4-Bromobutanoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Interchain doubly-bridged α-helical peptides for the development of protein binders》 were Chen, Yaqi; Liang, Jingjing; Li, Tao; Lin, Ping; Zhao, Yibing; Wu, Chuanliu. And the article was published in Chinese Chemical Letters in 2019. Computed Properties of C8H8Br2 The author mentioned the following in the article:

Constrained peptide scaffolds that are tolerant to extensive sequence manipulation and amenable to bioactive peptide design are of great value to the development of novel protein binders and peptide therapeutics. The authors reported strategies for the design and synthesis of a kind of novel interchain doubly-bridged α-helical peptides, involving mutual stabilization of two peptide α-helixes linked by two interchain bisthioether crosslinkers. By taking a MDM2-binding peptide with an α-helical tendency as a model, α-helical dimers with significantly improved structural and proteolytic stability and nanomolar binding affinity to the target protein can be obtained. By modulating the surface charges on the dimeric peptides, the authors also obtained a dimeric peptide with enhanced cell-penetrating capability, which can efficiently penetrate into cancer cells and inhibit the intracellular MDM2-p53 interactions to promote cell apoptosis. Considering that many proteins take a surface α-helical segment as the binding motif to mediate their interactions with other proteins, the authors believe that the authors’ interchain doubly-bridged α-helical peptides would provide a promising scaffold for the development of novel high-affinity protein binders.1,4-Bis(bromomethyl)benzene(cas: 623-24-5Computed Properties of C8H8Br2) was used in this study.

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. Computed Properties of C8H8Br2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《InBr3 as a self-defensed redox mediator for Li-O2 batteries: In situ construction of a stable indium-rich composite protective layer on the Li anode》 were Liu, Jia; Wu, Tong; Zhang, Siqi; Li, Dan; Wang, Ying; Xie, Haiming; Yang, Jinghai; Sun, Guiru. And the article was published in Journal of Power Sources in 2019. Formula: Br3In The author mentioned the following in the article:

One big obstacle for a redox mediator (RM)-based Li-O2 system is the redox shuttling between the diffusible RM+ and Li anode, leading to the unexpected RM degradation and continuous deterioration of Li anode, which inevitably results in a low energy efficiency and a poor cycling stability for the Li-O2 battery. Here, InBr3 as a self-defensed RM is firstly introduced into Li-O2 batteries, which can lower the cell overpotential and thus improve the cycling performance. Moreover, due to the In3+ existence, an In-rich composite protective layer can be in situ generated on the Li anode, which contributes to suppressing the redox shuttling, improving the interface stability of Li and electrolyte, and inhibiting the dendrite formation. This work gives an insight into the development of self-defensed RM and the protection of the Li anode for Li-O2 batteries. In the part of experimental materials, we found many familiar compounds, such as Indium(III) bromide(cas: 13465-09-3Formula: Br3In)

Indium(III) bromide(cas: 13465-09-3) is used in organic synthesis as a water tolerant Lewis acid. It efficiently catalyzes the three-component coupling of β-keto esters, aldehydes and urea (or thiourea) to afford the corresponding dihydropyrimidinones.Formula: Br3In

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2019,Chemistry of Materials included an article by Yuan, Yang; Li, Jiantang; Sun, Xiaodong; Li, Guanghua; Liu, Yunling; Verma, Gaurav; Ma, Shengqian. Product Details of 13465-09-3. The article was titled 《Indium-Organic Frameworks Based on Dual Secondary Building Units Featuring Halogen-Decorated Channels for Highly Effective CO2 Fixation》. The information in the text is summarized as follows:

Using a “”bifunctional ligand-directed strategy””, three isostructural indium-organic frameworks based on dual secondary building units (SBUs) were successfully constructed with targeted structures. In their frameworks, two types of unsaturated monomeric indium SBUs-[In(OOC-)2(-N-)X(H2O)] and [In(OOC-)2(-N-)X2]- (X = Cl, Br, and I; OOC- = dicarboxylphenyl-nicotinate) assemble to form 1D tubular channels with both open metal sites and weak base polarizing substituents. The trimeric indium SBUs [In3O(OOC-)6(DMA)3]+ serve as robust external linkers to extend into a 3D honeycomb double-walled framework with nanoscale channels. By changing the polarizing substituents in situ with different halogens (Cl-, Br-, and I-), three obtained isostructural MOFs show different channel characteristics, such as alkalinity of the polarizing substituents, acidity of the polarized open indium sites, extended channel sizes, and increased pore volumes (from -I to -Cl). Subsequently, the authors took the three MOFs collectively as a platform to investigate the impact of the different coordinated halide ions on channel functions, especially on CO2 adsorption and chem. conversion. Accordingly, the three nanochannel MOF catalysts exhibited highly effective performances in catalyzing cycloaddition of CO2 with large-sized epoxides, particularly styrene oxide, into value-added products-styrene carbonates with yields of 91-93% and high selectivity of 95-98%-under mild conditions. The authors speculated that the superior catalytic efficiencies of the three MOF catalysts could be ascribed to the synergistic effect of open indium sites as Lewis acid with different halide ions as weak base sites, which might enhance the catalytic selectivity through polarizing and activating CO2 mols. during the reaction process. After reading the article, we found that the author used Indium(III) bromide(cas: 13465-09-3Product Details of 13465-09-3)

Indium(III) bromide(cas: 13465-09-3) is used in organic synthesis as a water tolerant Lewis acid. It efficiently catalyzes the three-component coupling of β-keto esters, aldehydes and urea (or thiourea) to afford the corresponding dihydropyrimidinones.Product Details of 13465-09-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2019,MedChemComm included an article by Sharipova, Radmila R.; Belenok, Mayya G.; Garifullin, Bulat F.; Sapunova, Anastasiya S.; Voloshina, Alexandra D.; Andreeva, Olga V.; Strobykina, Irina Yu.; Skvortsova, Polina V.; Zuev, Yuriy F.; Kataev, Vladimir E.. Recommanded Product: (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate. The article was titled 《Synthesis and anti-cancer activities of glycosides and glycoconjugates of diterpenoid isosteviol》. The information in the text is summarized as follows:

A series of glycosides and glycoconjugates of diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) with various monosaccharide residues were synthesized and their cytotoxicity against some human cancer and normal cell lines was assayed. Most of the synthesized compounds demonstrated moderate to significant cytotoxicity against human cancer cell lines M-HeLa and MCF-7. Three lead compounds exhibited selective cytotoxic activities against M-HeLa (IC50 = 10.0-15.1μM) that were three times better than the cytotoxicity of the anti-cancer drug Tamoxifen (IC50 = 28.0μM). Moreover, the lead compounds were not cytotoxic with respect to the normal human cell line Chang liver (IC50 > 100μM), whereas Tamoxifen inhibited the viability of normal human Chang liver cells with an IC50 value of 46.0μM. It was determined that the cytotoxicity of the lead compounds was due to induction of apoptosis proceeding along the mitochondrial pathway. The cytotoxic activity of the synthesized compounds substantially depended on the nature of the monosaccharide residue and its position, i.e., whether the monosaccharide residue was attached directly to the isosteviol skeleton or was moved away from it by means of a polymethylene linker. After reading the article, we found that the author used (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3Recommanded Product: (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate)

(2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3) may be used for the synthesis of HMR1098-S-Glucuronide Methyl Ester, a new K-ATP-blocking agent being developed as a drug for prevention of sudden cardiac death.Recommanded Product: (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2019,Bioconjugate Chemistry included an article by Park, Suho; Kim, Sun Young; Cho, Jongun; Jung, Doohwan; Seo, Donghoon; Lee, Jaeho; Lee, Sangkwang; Yun, Sanghyeon; Lee, Hyangsook; Park, Okku; Seo, Beomseok; Woo, Sung Ho; Park, Tae Kyo. SDS of cas: 21085-72-3. The article was titled 《Aryl Sulfate is a Useful Motif for Conjugating and Releasing Phenolic Molecules: Sulfur Fluorine Exchange Click Chemistry Enables Discovery of Ortho-Hydroxy-Protected Aryl Sulfate Linker》. The information in the text is summarized as follows:

A new self-immolative linker motif, Ortho Hydroxy-Protected Aryl Sulfate (OHPAS), was devised, and OHPAS-containing antibody drug conjugates (ADC) were tested in vitro and in vivo. Conveniently synthesized using Sulfur Fluorine Exchange (SuFEx) chem., it is based structurally on diaryl sulfate, with one aryl acting as a payload and the other as a self-immolative sulfate unit having a latent phenol function at the ortho position. The chem. stable OHPAS linker was stable in plasma samples from 5 different species, yet it can release the payload mol. smoothly upon chem. or biol. triggering. The payload release proceeds via intramol. cyclization, producing a cyclic sulfate coproduct that eventually hydrolyzes to a catechol monosulfate. A set of OHPAS-containing ADCs based on Trastuzumab were prepared with a drug to antibody ratio of ∼2, and were shown to be cytotoxic in 5 different cancer cell lines in vitro and dose-dependently inhibited tumor growth in a NCI-N87 mouse xenograft model. We conclude that OHPAS conjugates will be of considerable use for delivering phenol-containing payloads to tissues targeted for medical intervention. The experimental process involved the reaction of (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3SDS of cas: 21085-72-3)

(2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate(cas: 21085-72-3) may be used for the synthesis of HMR1098-S-Glucuronide Methyl Ester, a new K-ATP-blocking agent being developed as a drug for prevention of sudden cardiac death.SDS of cas: 21085-72-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary