Tag: 100-200

《Systematic Investigation into the Formation of Significant Amounts of Unknown Impurity during Scale-up of NaBH4-I2 Mediated Reduction of Nitro-Amide Intermediate of Mirabegron》 was written by Deshmukh, Dattatray G.; Bangal, Mukund N.; Kalawade, Kaustubh A.; Mathad, Vijayavitthal T.. Synthetic Route of C6H11BrO2 And the article was included in Organic Process Research & Development in 2020. The article conveys some information:

After successful development of a manufacturing process for the Mirabegron (I) at the laboratory scale, a muddled situation was aroused during the scale-up batches, wherein sodium borohydride-iodine (NaBH4-I2) mediated reduction of nitro-amide II ended up with substantial amounts (∼10%) of unspecified impurity in the nitro-amine intermediate III. On the basis of the structure elucidation and meticulous investigation, a reaction path for its genesis during the process was identified and an efficient mechanism proposed to arrest its formation. In-situ generated nickel boride (Ni2B) due to reaction of NiI2 (corrosion product) with NaBH4 followed by electrophilic attack of THF (solvent) was found to be the reason for the formation of impurity (IV). Execution of subsequent batches with proper controls arrested this impurity and successfully provided the Mirabegron with the desired quality. In the experiment, the researchers used Ethyl 4-bromobutyrate(cas: 2969-81-5Synthetic Route of C6H11BrO2)

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.Synthetic Route of C6H11BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Isothiourea-Catalyzed Atropselective Acylation of Biaryl Phenols via Sequential Desymmetrization/Kinetic Resolution》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Munday, Elizabeth S.; Grove, Markas A.; Feoktistova, Taisiia; Brueckner, Alexander C.; Walden, Daniel M.; Young, Claire M.; Slawin, Alexandra M. Z.; Campbell, Andrew D.; Cheong, Paul Ha-Yeon; Smith, Andrew D.. Reference of 1-Bromo-2-isopropylbenzene The article mentions the following:

Nonracemic biaryldiol monoesters such as I were prepared by desymmetrization of racemic biaryldiols with isobutyric anhydride and diisopropylethylamine in CH2Cl2 in the presence of nonracemic imidazo- or pyrimidobenzothiazoles. The optimal catalyst depended on the substitution pattern of the biaryldiol. The kinetics of the reaction were determined to understand the enantioselectivity of the acylation; the observed enantioselectivity is a result of an enantioselective desymmetrization coupled to a chiroablative kinetic resolution The free energies and structures of potential transition states were determined using DFT calculations to understand the factors leading to high enantiocontrol; maintenance of substrate planarity to maximize a 1,5-S···O interaction within the key acyl ammonium intermediate is the major determinant of acylation selectivity and thus product enantioselectivity. In the experiment, the researchers used many compounds, for example, 1-Bromo-2-isopropylbenzene(cas: 7073-94-1Reference of 1-Bromo-2-isopropylbenzene)

1-Bromo-2-isopropylbenzene(cas: 7073-94-1) belongs to organobromine compounds.Depending on the type of carbon to which the bromine is bonded, organic bromide could be alkyl, alkenyl, alkynyl, or aryl. Reference of 1-Bromo-2-isopropylbenzene Due to the reactivity of bromide, they are used as potential precursors or important intermediates in organic synthesis.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Switchable Solvatochromic Probes for Live-Cell Super-resolution Imaging of Plasma Membrane Organization》 were Danylchuk, Dmytro I.; Moon, Seonah; Xu, Ke; Klymchenko, Andrey S.. And the article was published in Angewandte Chemie, International Edition in 2019. Name: Ethyl 4-bromobutyrate The author mentioned the following in the article:

Visualization of the nanoscale organization of cell membranes remains challenging because of the lack of appropriate fluorescent probes. Herein, we introduce a new design concept for super-resolution microscopy probes that combines specific membrane targeting, on/off switching, and environment sensing functions. A functionalization strategy for solvatochromic dye Nile Red that improves its photostability is presented. The dye is grafted to a newly developed membrane-targeting moiety composed of a sulfonate group and an alkyl chain of varied lengths. While the long-chain probe with strong membrane binding, NR12A, is suitable for conventional microscopy, the short-chain probe NR4A, owing to the reversible binding, enables first nanoscale cartog. of the lipid order exclusively at the surface of live cells. The latter probe reveals the presence of nanoscopic protrusions and invaginations of lower lipid order in plasma membranes, suggesting a subtle connection between membrane morphol. and lipid organization. In the experiment, the researchers used Ethyl 4-bromobutyrate(cas: 2969-81-5Name: Ethyl 4-bromobutyrate)

Ethyl 4-bromobutyrate(cas: 2969-81-5) belongs to bromides. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Name: Ethyl 4-bromobutyrate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

The author of 《Mechanistic Characterization of (Xantphos)Ni(I)-Mediated Alkyl Bromide Activation: Oxidative Addition, Electron Transfer, or Halogen-Atom Abstraction》 were Diccianni, Justin B.; Katigbak, Joseph; Hu, Chunhua; Diao, Tianning. And the article was published in Journal of the American Chemical Society in 2019. SDS of cas: 7051-34-5 The author mentioned the following in the article:

Ni(I)-mediated single-electron oxidative activation of alkyl halides has been extensively proposed as a key step in Ni-catalyzed cross-coupling reactions to generate radical intermediates. There are four mechanisms through which this step could take place: oxidative addition, outer-sphere electron transfer, inner-sphere electron transfer, and concerted halogen-atom abstraction. Despite considerable computational studies, there is no exptl. study to evaluate all four pathways for Ni(I)-mediated alkyl radical formation. Herein, we report the isolation of a series of (Xantphos)Ni(I)-Ar complexes that selectively activate alkyl halides over aryl halides to eject radicals and form Ni(II) complexes. This observation allows the application of kinetic studies on the steric, electronic, and solvent effects, in combination with DFT calculations, to systematically assess the four possible pathways. Our data reveal that (Xantphos)Ni(I)-mediated alkyl halide activation proceeds via a concerted halogen-atom abstraction mechanism. This result corroborates previous DFT studies on (terpy)Ni(I)- and (py)Ni(I)-mediated alkyl radical formation, and contrasts with the outer-sphere electron transfer pathway observed for (PPh3)4Ni(0)-mediated aryl halide activation. This study of a model system provides insight into the overall mechanism of Ni-catalyzed cross-coupling reactions and offers a basis for differentiating electrophiles in cross-electrophile coupling reactions. In the experiment, the researchers used (Bromomethyl)cyclopropane(cas: 7051-34-5SDS of cas: 7051-34-5)

(Bromomethyl)cyclopropane(cas: 7051-34-5) is used as a synthetic building block for the introduction of the cyclopropylmethyl group. It was also used in the synthesis of 1,4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents.SDS of cas: 7051-34-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2019,European Journal of Pharmaceutical Sciences included an article by Trivedi, Prakruti; Adhikari, Nilanjan; Amin, Sk. Abdul; Bobde, Yamini; Ganesh, Routholla; Jha, Tarun; Ghosh, Balaram. Name: Methyl 3-bromopropanoate. The article was titled 《Design, synthesis, biological evaluation and molecular docking study of arylcarboxamido piperidine and piperazine-based hydroxamates as potential HDAC8 inhibitors with promising anticancer activity》. The information in the text is summarized as follows:

Some new hydroxamate derivatives with alkylpiperidine and alkylpiperazine linker moieties were designed, synthesized and biol. evaluated. All these compounds were effective HDAC8 inhibitors comprising more or less similar cytotoxic potential against different cancer cell lines. It was observed that the piperazine scaffold containing compound was more active than the compound with piperidine scaffold for exerting HDAC8 inhibitory activity. Moreover, the 4-quinolyl cap group was better than the biphenyl group which was better than the benzyl group for producing higher HDAC8 inhibition as well as cytotoxicity. These compounds displayed selective HDAC8 inhibition over HDAC3. Moreover, these compounds showed an increased caspase3/7 activity suggesting their anticancer potential through modulation of apoptotic pathways. Mol. docking study with three potent compounds was performed with both HDAC3 and HDAC8 enzymes to understand the selectivity profile of these compounds Compound containing 4-quinolyl cap group with alkyl piperazinyl urea linker moiety was emerged out as the lead mol. that may be further modified to design more effective and selective HDAC8 inhibitors in future. In the experimental materials used by the author, we found Methyl 3-bromopropanoate(cas: 3395-91-3Name: Methyl 3-bromopropanoate)

Methyl 3-bromopropanoate(cas: 3395-91-3) 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.Name: Methyl 3-bromopropanoate

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2017,Bag, Subhendu Sekhar; Yashmeen, Afsana published 《Uracil-amino acid as a scaffold for β-sheet peptidomimetics: Study of photophysics and interaction with BSA protein》.Bioorganic & Medicinal Chemistry Letters published the findings.Recommanded Product: 3395-91-3 The information in the text is summarized as follows:

We report herein the uracil-di-aza-amino acid (UrAA) as a new family of mol. scaffold to induce β-hairpin structure with H-bonded β-sheet conformation in a short peptide. This has been demonstrated in two conceptual fluorescent pentapeptides wherein triazolylpyrenyl alanine and/or triazolylmethoxynaphthyl alanine (TPyAlaDo and/or TMNapAlaDo) are embedded into two arms of the uracil-amino acid via an intervening leucine. Conformational anal. by CD, IR, variable temperature and 2D NMR spectroscopy reveals the β-hairpin structures for both the peptides. Study of photophys. property reveals that the pentapeptide containing fluorescent triazolyl unnatural amino acids TMNapAlaDo and TPyAlaDo at the two termini exhibits dual path entry to exciplex emission-either via FRET from TMNapAlaDo to TPyAlaDo or via direct excitation of a FRET acceptor, TPyAlaDo. The other pentapeptide with TPyAlaDo/TPyAlaDo pair shows excimer emission. Furthermore, both the peptides maintaining their fundamental photophysics are found to interact with BSA as only a test biomol. In the experimental materials used by the author, we found Methyl 3-bromopropanoate(cas: 3395-91-3Recommanded Product: 3395-91-3)

Methyl 3-bromopropanoate(cas: 3395-91-3) belongs to bromides. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Recommanded Product: 3395-91-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Product Details of 3395-91-3In 2020 ,《Thermally Activated Delayed Fluorescence Benzyl Cellulose Derivatives for Nondoped Organic Light-Emitting Diodes》 was published in Macromolecules (Washington, DC, United States). The article was written by Shibano, Masaya; Ochiai, Hiroki; Suzuki, Katsuaki; Kamitakahara, Hiroshi; Kaji, Hironori; Takano, Toshiyuki. The article contains the following contents:

Thermally activated delayed fluorescence (TADF)-benzyl cellulose derivatives (TBC-X), which contained both carbazole (host) and phthalimide-based TADF dye (guest) moieties, were prepared from 2,3-di-O-benzyl cellulose in high yields. The TBC-X samples were soluble in common organic solvents such as CH2Cl2, CHCl3, THF, and toluene. The photoluminescence spectra of TBC-X spin-coated films had a single emission peak derived only from guest moieties, which indicated efficient energy transfer from the host to guest moieties. The TBC-10 (with a content of host and guest moieties of 93 and 7, resp.) in a spin-coated film had the highest photoluminescence quantum yield of 55.3% and TADF characteristics. A nondoped organic light emitting diode with TBC-10 as the emitting layer showed green emission (λEL = 517 nm) and achieved a maximum external quantum efficiency of 5.9%. The results came from multiple reactions, including the reaction of Methyl 3-bromopropanoate(cas: 3395-91-3Product Details of 3395-91-3)

Methyl 3-bromopropanoate(cas: 3395-91-3) belongs to bromides. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Product Details of 3395-91-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Safety of (Bromomethyl)cyclopropaneIn 2019 ,《Dual nickel- and photoredox-catalyzed reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides》 was published in Chemical Communications (Cambridge, United Kingdom). The article was written by Yu, Weijie; Chen, Long; Tao, Jiasi; Wang, Tao; Fu, Junkai. The article contains the following contents:

A novel reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides was realized via photoredox/nickel dual catalysis to produce vinyl arene derivatives bearing all-carbon quaternary centers with excellent E-selectivity. A stoichiometric metal reductant was avoided by employing com. available N,N,N’,N’-tetramethylethylenediamine (TMEDA) as the terminal reductant. In the experiment, the researchers used many compounds, for example, (Bromomethyl)cyclopropane(cas: 7051-34-5Safety of (Bromomethyl)cyclopropane)

(Bromomethyl)cyclopropane(cas: 7051-34-5) is used as a synthetic building block for the introduction of the cyclopropylmethyl group. It was also used in the synthesis of 1,4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents.Safety of (Bromomethyl)cyclopropane

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2022,Johnson, John Douglas; Teeples, Charles Reece; Akkawi, Nicholas Rajai; Wilkerson-Hill, Sidney M. published an article in Journal of the American Chemical Society. The title of the article was 《Efficient Synthesis of Orphaned Cyclopropanes Using Sulfones as Carbene Equivalents》.Formula: C4H7Br The author mentioned the following in the article:

Herein, a mechanistically distinct platform to transfer 1,1-dialkylcarbene units to olefins using carbometalation reactions of dialkyl sulfonyl anions was introduced. In presence of NaNH2 or n-BuLi in ethereal solvents, dialkyl sulfones reacted with styrenes and arylbutadienes between 23 and 70°C to produce corresponding 1,1-dialkylcyclopropanes, e.g., I [R1 = Me, Et, n-Bu, etc.; R2 = H, i-Bu, n-pentadecyl, etc.; R1R2 = (CH2)4, (CH2)5, (CH2)6]. Forty examples of this reactivity including 16 different styrenes (up to 89% isolated yield), 9 arylbutadienes (51-88% yield), and 13 different sulfones (46-80% yield) was reported. In addition, an example of a sequential cyclopropanation reaction using this method was reported. Preliminary mechanistic studies suggested a stepwise anionic process that was initiated by direct addition of sulfonyl anions to a carbon-carbon double bond. In the experiment, the researchers used (Bromomethyl)cyclopropane(cas: 7051-34-5Formula: C4H7Br)

(Bromomethyl)cyclopropane(cas: 7051-34-5) is used as a synthetic building block for the introduction of the cyclopropylmethyl group. It was also used in the synthesis of 1,4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents.Formula: C4H7Br

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Kretschmer, Nadine; Hufner, Antje; Durchschein, Christin; Popodi, Katrin; Rinner, Beate; Lohberger, Birgit; Bauer, Rudolf published an article in 2021. The article was titled 《Synthesis and pharmacological in vitro investigations of novel shikonin derivatives with a special focus on cyclopropane bearing derivatives》, and you may find the article in International Journal of Molecular Sciences.Application of 2623-87-2 The information in the text is summarized as follows:

In previous studies, author’s showed that the constituents of the roots of Onosma paniculata as well as a synthetic derivative of the most active constituent showed promising results in metastatic melanoma cell lines. In the current study, author’s address the question whether author’s can generate further derivatives with optimized activity by synthesis. Therefore, author’s prepared 31, mainly novel shikonin derivatives and screened them in different melanoma cell lines (WM9, WM164, and MUG-Mel2 cells) using the XTT viability assay. Author’s identified (R)-1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl 2-cyclopropyl-2-oxoacetate as a novel derivative with even higher activity. Furthermore, pharmacol. investigations including the ApoToxGloM Triplex assay, LDH assay, and cell cycle measurements revealed that this compound induced apoptosis and reduced cells in the G1 phase accompanied by an increase of cells in the G2/M phase. Moreover, it showed hardly any effects on the cell membrane integrity. However, it also exhibited cytotoxicity against non-tumorigenic cells. Nevertheless, in summary, author’s could show that shikonin derivatives might be promising drug leads in the treatment of melanoma. 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