Month: October 2022

Application In Synthesis of 9,10-DibromoanthraceneIn 2021 ,《Tackling Solubility Issues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble Aryl Halides》 was published in Journal of the American Chemical Society. The article was written by Seo, Tamae; Toyoshima, Naoki; Kubota, Koji; Ito, Hajime. The article contains the following contents:

Conventional organic synthesis generally relies on the use of liquid organic solvents to dissolve the reactants. Therefore, reactions of sparingly soluble or insoluble substrates are challenging and often ineffective. The development of a solvent-independent solid-state approach that overcomes this longstanding solubility issue would provide innovative synthetic solutions and access to new areas of chem. space. Here, we report extremely fast and highly efficient solid-state palladium-catalyzed Suzuki-Miyaura cross-coupling reactions via a high-temperature ball-milling technique. This solid-state protocol enables the highly efficient cross-couplings of insoluble aryl halides with large polyaromatic structures that are barely reactive under conventional solution-based conditions. Notably, we discovered a new luminescent organic material with a strong red emission. This material was prepared via the solid-state coupling of Pigment violet 23, a compound that has so far not been involved in mol. transformations due to its extremely low solubility This study thus provides a practical method for accessing unexplored areas of chem. space through mol. transformations of insoluble organic compounds that cannot be carried out by any other approach. After reading the article, we found that the author used 9,10-Dibromoanthracene(cas: 523-27-3Application In Synthesis of 9,10-Dibromoanthracene)

9,10-Dibromoanthracene(cas: 523-27-3) is a dibrominated polycyclic aromatic hydrocarbon (PAH). 9,10-Dibromoanthracene is often used as an energy acceptor and activator in reactions that produce chemiluminescence.Application In Synthesis of 9,10-Dibromoanthracene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of C8H8Br2In 2019 ,《Tetrameric (Bi4I16)4- Iodobismuthate Templated by 1,ω-Bis(isoquinoline)alkane cation: structure, photoluminescence and enhanced thermochromism》 was published in Chinese Journal of Structural Chemistry. The article was written by Wang, Penga; Chen, Zhi-Rong; Li, Hao-Hong. The article contains the following contents:

Using 1,1′-bis(isoquinoline)-1,4-phenyldimethylenyl (BIQPM2+) cation as template, a new tetrameric (Bi4I16)4- iodobismuthate-containing hybrid with formula of (BIQPM)2(Bi4I16)•H2O (1), has been prepared under solvothermal conditions. The centrosym. Bi4I164- tetraanion is constructed from four edge-shared slightly distorted BiI6 octahedrons. Due to the presence of larger conjugated system (isoquinoline ring), strong π•••π stacking interactions can be observed Besides, strong I•••I interactions can be monitored and extends the 0-D Bi4I164- cluster to a quasi-1-D chain. The smaller energy gap of 2.13 eV is led by these non-covalent interactions. Its IR emission might be caused by strong charge transfer between anions and cations. Furthermore, the reversible thermochromic behavior with low chromotropic temperature of 80° can be observed, whose mechanism was discussed. In the experiment, the researchers used 1,4-Bis(bromomethyl)benzene(cas: 623-24-5Synthetic Route of C8H8Br2)

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. Synthetic Route of C8H8Br2 In contrast, terrestrial plants account only for a few bromine-containing compounds.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

COA of Formula: C18H12Br3NIn 2020 ,《Effects of structural variations on π-dimer formation: long-distance multicenter bonding of cation-radicals of tetrathiafulvalene analogues》 was published in Physical Chemistry Chemical Physics. The article was written by Brown, John T.; Zeller, Matthias; Rosokha, Sergiy V.. The article contains the following contents:

The multicenter (pancake) bonding between cation-radicals of tetramethyltetraselenafulvalene, TMTSF+ ̇, tetramethyltetrathiafulvalene, TMTTF+ ̇, and bis(ethylenedithio)-tetrathiafulvalene, ET+, ̇was compared to that of tetrathiafulvalene, TTF+ ̇. To minimize counter-ion effects, the cation-radical salts with weakly coordinating anions (WCA), tetrakis(3,5-trifluoromethylphenyl)borate, dodecamethylcarborane and hexabromocarborane were prepared Solid-state (X-ray and EPR) measurements revealed diamagnetic π-dimers in the TMTSF and ET salts and the sep. monomers in the TTF salts with all WCAs, while TMTTF existed as a dimer in one and a monomer in two salts. The variable-temperature UV-Vis studies of these salts in solution showed that the thermodn. of formation of the π-bonded dimers of TMTTF+ ̇was close to that of TTF+ ̇, while TMTSF+ ̇and ET+ ̇showed a higher propensity for π-dimerization. These data indicated that the replacement of sulfur with heavier selenium or insertion of ethylenedithia-substituents into the TTF core increases the π-dimers’ stability. Yet, computational anal. indicated that the weakly covalent component of π-bonding decreases in the order TTF > TMTTF > TMTSF > ET. The higher stability of the π-dimers of TMTSF+ ̇and ET+ ̇cation-radicals was related to a decrease of the electrostatic repulsion between cationic counter-parts and an increase of dispersion components in these associations In the part of experimental materials, we found many familiar compounds, such as Tris(4-bromophenyl)amine(cas: 4316-58-9COA of Formula: C18H12Br3N)

In general, Tris(4-bromophenyl)amine(cas: 4316-58-9) is often used in the synthesis of porous luminescent covalent–organic polymers (COPs)COA of Formula: C18H12Br3N

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Application of 3141-27-3In 2021 ,《Donor-Acceptor-Donor Thienopyrazine-Based Dyes as NIR-Emitting AIEgens》 was published in European Journal of Organic Chemistry. The article was written by Goti, Giulio; Calamante, Massimo; Coppola, Carmen; Dessi, Alessio; Franchi, Daniele; Mordini, Alessandro; Sinicropi, Adalgisa; Zani, Lorenzo; Reginato, Gianna. The article contains the following contents:

Organic Near-IR luminophores have found broad application as functional materials, but the development of efficient NIR emitters is still a challenging goal. Here we report on a new class of thieno[3,4-b]pyrazine-based NIR emitting materials with Aggregation Induced Emission (AIE) properties. The dyes feature a donor-acceptor-donor (D-A-D) structure, with a thienopyrazine acceptor core connected to two triarylamine donor groups bearing a tetraphenylethylene (TPE) moiety. Fast and efficient synthesis allowed the modular preparation of three dyes of tunable absorption and emission profiles. These constructs were extensively characterized by spectroscopic studies in different solvents, which revealed intense light-harvesting ability and emissions in the deep-red and NIR region with large Stokes shift values. Remarkably, the dyes exhibited AIE properties, retaining emissive ability in the aggregate state, thus emerging as attractive materials for their potential application in the development of luminescent devices. In the experiment, the researchers used 2,5-Dibromothiophene(cas: 3141-27-3Application of 3141-27-3)

2,5-Dibromothiophene(cas: 3141-27-3) , is mainly used as pharmaceutical intermediate and synthesis intermediate. 2,5-Dibromothiophene polymerizes by debromination with magnesium catalyzed by nickel compounds to form poly(2,5- thienylene) .Application of 3141-27-3

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Design and synthesis of 7-O-1,2,3-triazole hesperetin derivatives to relieve inflammation of acute liver injury in mice》 was written by Zheng, Yan; Zhang, Yi-long; Li, Zeng; Shi, Wen; Ji, Ya-ru; Guo, Ya-Hui; Huang, Cheng; Sun, Guo-ping; Li, Jun. Name: (Bromomethyl)cyclopropaneThis research focused ontriazole hesperetin derivative preparation treatment inflammation acute liver injury; Anti-inflammatory activity introduction; Hesperetin; Structure-activity relationships; Synthesis; Triazole. The article conveys some information:

Based on the previous research results of our research group, to further improve the anti-inflammatory activity of hesperetin, we substituted triazole at the 7-OH branch of hesperetin. We also evaluated the anti-inflammatory activity of 39 new hesperetin derivatives All compounds showed inhibitory effects on nitric oxide (NO) and inflammatory factors in lipopolysaccharide-induced RAW264.7 cells. Compound I, 4-hydroxyimino-7-O-((1-propyl-1H-1,2,3-triazol-4-yl)methyl)hesperetin showed a strong inhibitory effect on NO (half maximal inhibitory concentration = 2.34 ± 0.7μM) and tumor necrosis factor-α, interleukin (IL)-1β, and (IL-6). Structure-activity relationships indicate that 7-O-triazole is buried in a medium-sized hydrophobic cavity that binds to the receptor. Compound 4-hydroxyimino-7-O-((1-propyl-1H-1,2,3-triazol-4-yl)methyl)hesperetin can also reduce the reactive oxygen species production and significantly inhibit the expression of inducible NO synthase and cyclooxygenase-2 through the nuclear factor-κB signaling pathway. In vivo results indicate that compound I can reduce liver inflammation in mice with acute liver injury (ALI) induced by CCI4, and may be a candidate drug for treating inflammation associated with ALI. In the experimental materials used by the author, we found (Bromomethyl)cyclopropane(cas: 7051-34-5Name: (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.Name: (Bromomethyl)cyclopropane

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《Identification and optimization of biphenyl derivatives as novel tubulin inhibitors targeting colchicine-binding site overcoming multidrug resistance》 was written by Cheng, Bao; Zhu, Guirong; Meng, Linghua; Wu, Guolin; Chen, Qin; Ma, Shengming. Reference of 1-Bromo-3,4,5-trimethoxybenzeneThis research focused ontubulin optimization biphenyl colchicine multidrug resistance; Anticancer activity; Biphenyl derivatives; Multidrug resistance; Tubulin inhibitors. The article conveys some information:

Microtubule targeting agents (MTAs) are among the most successful chemotherapeutic drugs, but their efficacy is often limited by the development of multidrug resistance (MDR). Therefore, the development of novel MTAs with the ability to overcome MDR is urgently needed. In this contribution, through modification of the unsym. biaryl compounds, we discovered a novel compound dxy-1-175 with potent anti-proliferative activity against cancer cells. Mechanistic study revealed that dxy-1-175 inhibited tubulin polymerization by interacting with the colchicine-binding site of tubulin, which caused cell cycle arrest at G2/M phase. Based on the predicted binding model of dxy-1-175 with tubulin, a series of new 4-benzoylbiphenyl analogs were designed and synthesized. Among them, the hydrochloride compound 12e with improved solubility and good stability in human liver microsome, exhibited the most potent anti-proliferative activity with IC50 value in the low nanomolar range, and markedly inhibited the growth of breast cancer 4T1 xenograft in vivo. Notably, 12e effectively overcame P-gp-mediated MDR and our preliminary data suggested that 12e may not be a substrate of P-glycoprotein (P-gp). Taken together, our study reveals a novel MTA 12e targeting the colchicine-binding site with potent anticancer activity and the ability to circumvent MDR. In addition to this study using 1-Bromo-3,4,5-trimethoxybenzene, there are many other studies that have used 1-Bromo-3,4,5-trimethoxybenzene(cas: 2675-79-8Reference of 1-Bromo-3,4,5-trimethoxybenzene) was used in this study.

1-Bromo-3,4,5-trimethoxybenzene(cas: 2675-79-8) is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.Reference of 1-Bromo-3,4,5-trimethoxybenzene1-Bromo-3,4,5-trimethoxybenzene can be used to synthesize analogs of HA14-1, which shows promising anticancer properties.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

《XCage: A Tricyclic Octacationic Receptor for Perylene Diimide with Picomolar Affinity in Water》 was written by Liu, Wenqi; Bobbala, Sharan; Stern, Charlotte L.; Hornick, Jessica E.; Liu, Yugang; Enciso, Alan E.; Scott, Evan A.; Stoddart, J. Fraser. Product Details of 623-24-5This research focused onXCage tricyclic octacationic receptor perylene diimide fluorescence. The article conveys some information:

The rational design of wholly synthetic receptors that bind active substrates with ultrahigh affinities is a challenging goal, especially in water. Here, we report the synthesis of a tricyclic octacationic cyclophane, which exhibits complementary stereoelectronic binding toward a widely used fluorescent dye, perylene diimide, with picomolar affinity in water. The ultrahigh binding affinity is sustained by a large and rigid hydrophobic binding surface, which provides a highly favorable enthalpy and a slightly pos. entropy of complexation. The receptor-substrate complex shows significant improvement in optical properties, including red-shifted absorption and emission, turn-on fluorescence, and efficient energy transfer. An unusual single-excitation, dual-emission, imaging study of living cells was performed by taking advantage of a large pseudo-Stokes shift, produced by the efficient energy transfer. In the experiment, the researchers used many compounds, for example, 1,4-Bis(bromomethyl)benzene(cas: 623-24-5Product Details of 623-24-5)

1,4-Bis(bromomethyl)benzene(cas: 623-24-5) 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. Product Details of 623-24-5 Dehydrobromination, Grignard reactions, reductive coupling, Wittig reaction, and several nucleophilic substitution reactions are some of the principal reactions which involve organic bromides.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2018,Physical Chemistry Chemical Physics included an article by Peyrot, David; Silly, Mathieu G.; Silly, Fabien. Application of 29102-67-8. The article was titled 《X3 synthon geometries in two-dimensional halogen-bonded 1,3,5-tris(3,5-dibromophenyl)benzene self-assembled nanoarchitectures on Au(111)-(22×sqrt.3)》. The information in the text is summarized as follows:

The self-assembly of star-shaped 1,3,5-tris(3,5-dibromophenyl)benzene mols. on Au(111)-(22×sqrt.3) in a vacuum is investigated using scanning tunneling microscopy and core-level spectroscopy. Scanning tunneling microscopy shows that the mols. self-assemble into a hexagonal porous halogen-bonded nanoarchitecture. This structure is stabilized by X3-A synthons composed of three type-II halogen-interactions (halogen-bonds). The mols. are oriented along the same direction in this arrangement. Domain boundaries are observed in the hcp region of the herringbone gold surface reconstruction. Mols. of the neighboring domains are rotated by 180°. The domain boundaries are stabilized by the formation of X3-B synthons composed of two type-II and one type-I halogen-interactions between mols. of the neighboring domains. Core-level spectroscopy confirms the existence of two types of halogen-interactions in the organic layer. These observations show that the gold surface reconstructions can be exploited to modify the long-range supramol. halogen-bonded self-assemblies. The experimental part of the paper was very detailed, including the reaction process of 3,3”,5,5”-Tetrabromo-5′-(3,5-dibromophenyl)-1,1′:3′,1”-terphenyl(cas: 29102-67-8Application of 29102-67-8)

3,3”,5,5”-Tetrabromo-5′-(3,5-dibromophenyl)-1,1′:3′,1”-terphenyl(cas: 29102-67-8) belongs to organobromine compounds.Organobromine chemicals are produced naturally by an array of biological and other chemical processes in our environment. Organobromine compounds are produced naturally by marine creatures (sponges, corals, sea slugs, tunicates, sea fans) and seaweed, plants, fungi, lichen, algae, bacteria, microbes, and some mammals. Application of 29102-67-8

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Li, Zexian; Wang, Minyan; Shi, Zhuangzhi published an article on January 4 ,2021. The article was titled 《Radical Addition Enables 1,2-Aryl Migration from a Vinyl-Substituted All-Carbon Quaternary Center》, and you may find the article in Angewandte Chemie, International Edition.Electric Literature of C4H6BrFO2 The information in the text is summarized as follows:

An efficient method for photocatalytic perfluoroalkylation of vinyl-substituted all-carbon quaternary centers involving 1,2-aryl migration was developed. The rearrangement reactions use fac-Ir(ppy)3, visible light and com. available fluoroalkyl halides and can generate valuable multisubstituted perfluoroalkylated compounds in a single step that would be challenging to prepare by other methods. Mechanistically, the photoinduced alkyl radical addition to an alkene leads to the migration of a vicinal aryl substituent from its adjacent all-carbon quaternary center with the concomitant generation of a C-radical bearing two electron-withdrawing groups that is further reduced by a hydrogen donor to complete the domino sequence. In the experiment, the researchers used Ethylbromofluoroacetate(cas: 401-55-8Electric Literature of C4H6BrFO2)

Ethylbromofluoroacetate(cas: 401-55-8) is a member of organofluorine compounds. Organofluorine compounds, which have carbon-fluorine bonds, show unique features such as high thermal and chemical stability, high surface activity, no light-absorbing ability, high pharmacological effect, and so on. Owing to their specific characters, they are indispensable chemicals for industry and our daily lives.Electric Literature of C4H6BrFO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Schneider, Leon N.; Tanzer Krauel, Eva-Maria; Deutsch, Carl; Urbahns, Klaus; Bischof, Tobias; Maibom, Kristina A. M.; Landmann, Johannes; Keppner, Fabian; Kerpen, Christoph; Hailmann, Michael; Zapf, Ludwig; Knuplez, Tanja; Bertermann, Ruediger; Ignat’ev, Nikolai V.; Finze, Maik published an article in Chemistry – A European Journal. The title of the article was 《Stable and Storable N(CF3)2 Transfer Reagents》.Application In Synthesis of 4-Bromo-1-(bromomethyl)-2-fluorobenzene The author mentioned the following in the article:

Fluorinated groups are essential for drug design, agrochems., and materials science. The bis(trifluoromethyl)amino group is an example of a stable group that has a high potential. While the number of mols. containing perfluoroalkyl, perfluoroalkoxy, and other fluorinated groups is steadily increasing, examples with the N(CF3)2 group are rare. One reason is that transfer reagents are scarce and metal-based storable reagents are unknown. Herein, a set of CuI and AgI bis(trifluoromethyl)amido complexes stabilized by N- and P-donor ligands with unprecedented stability are presented. The complexes are stable solids that can even be manipulated in air for a short time. They are bis(trifluoromethyl)amination reagents as shown by nucleophilic substitution and Sandmeyer reactions. In addition to a series of benzylbis(trifluoromethyl)amines, 2-bis(trifluoromethyl)amino acetate was obtained, which, upon hydrolysis, gives the fluorinated amino acid-N,N-bis(trifluoromethyl)glycine.4-Bromo-1-(bromomethyl)-2-fluorobenzene(cas: 76283-09-5Application In Synthesis of 4-Bromo-1-(bromomethyl)-2-fluorobenzene) was used in this study.

4-Bromo-1-(bromomethyl)-2-fluorobenzene(cas: 76283-09-5) 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. Application In Synthesis of 4-Bromo-1-(bromomethyl)-2-fluorobenzene Alkyl bromides are mainly used as alkylating agents and also find application as a solvent to extract oil from seeds and wool.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary