Month: October 2022

Bai, Hongyuan; Han, Li; Li, Wei; Li, Chao; Zhang, Songbo; Wang, Xuefei; Yin, Yu; Yan, Hong; Ma, Hongwei published their research in Macromolecules (Washington, DC, United States) in 2021. The article was titled 《C5 and C6 Polymerizations by Anion Migrated Ring-Opening of 1-Cyclopropylvinylbenzene and 1-Cyclobutylvinylbenzene》.Category: bromides-buliding-blocks The article contains the following contents:

As an emerging method, anion migrated ring-opening polymerization (AMROP) can effectively regulate the carbon skeletons of polymer backbones with specific vinyl monomers. As reported here, polymers with C5 and C6 skeletons were synthesized by AMROP of 1-cyclopropylvinylbenzene (CPVB) and 1-cyclobutylvinylbenzene (CBVB). Moreover, C4 polymerization of 1-phenyl-1,3-butadiene (1-PB) was also conducted (in a general anionic polymerization process) for comparison with C5 and C6 polymerizations Among the three base polymers prepared with the C4, C5, and C6 polymerizations, PCBVB exhibited the most flexible carbon skeleton structure and the lowest glass transition temperature (Tg = -18.8°C). Then, the resultant base polymers with different carbon skeletons were hydrogenated and cyclized. The hydrogenation of P(1-PB), PCPVB, and PCBVB resulted in the formation of products with unique alternating styrene/ethylene (alt-SE), periodic styrene/ethylene/methylene (pd-SEM), and periodic styrene/ethylene/ethylene (pd-SEE) structures. Moreover, pd-SEM and pd-SEE can be considered as sequence-defined template polymers, and these structures cannot be synthesized through general copolymerization of styrene and ethylene. Owing to the specific carbon skeletons exhibited in alt-SE, pd-SEM, and pd-SEE, their Tg values showed significant differences (24.6, 10.9, and -6.0°C, resp.). Addnl., the specific carbon skeletons of the base polymers resulted in the formation of cyclized polymers with different annular substituents. Moreover, diverse annular substitutes endowed the cyclized polymers with prominent thermal resistance and luminescence properties. Through the above investigations, it is clearly demonstrated that small changes in carbon skeleton structure can remarkably affect the polymer properties. Moreover, AMROP provides a new strategy to design novel polymers with C5 and C6 skeleton structures.Methyltriphenylphosphonium bromide(cas: 1779-49-3Category: bromides-buliding-blocks) was used in this study.

Methyltriphenylphosphonium bromide(cas: 1779-49-3) is used for methylenation through the Wittig reaction. It is utilized in the synthesis of an enyne and 9-isopropenyl -phenanthrene by using sodium amide as reagent. Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Delcaillau, Tristan; Boehm, Philip; Morandi, Bill published their research in Journal of the American Chemical Society in 2021. The article was titled 《Nickel-Catalyzed Reversible Functional Group Metathesis Between Aryl Nitriles And Aryl Thioethers》.Application In Synthesis of 5-Bromobenzo[d][1,3]dioxole The article contains the following contents:

A new functional group metathesis between aryl nitriles and aryl thioethers via nickel/dcype catalysis to achieve fully reversible transformation to afford aryl nitriles R-CN [R = 4-tBuC6H4, 3-FC6H4, 2-naphthyl, etc.] and aryl thioethers R1-SMe [R1 = 4-NCC6H4, 2-pyridyl, 4-F3CC6H4, etc.] in good to excellent yields was reported. Furthermore, the cyanide and thiol-free reaction showed high functional-group tolerance and great efficiency for late-stage derivatization of com. mols. Finally, synthetic applications demonstrated its versatility and utility in multistep synthesis. In the experimental materials used by the author, we found 5-Bromobenzo[d][1,3]dioxole(cas: 2635-13-4Application In Synthesis of 5-Bromobenzo[d][1,3]dioxole)

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.Application In Synthesis of 5-Bromobenzo[d][1,3]dioxole

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

O’Connor, Thomas J.; Mai, Binh Khanh; Nafie, Jordan; Liu, Peng; Toste, F. Dean published their research in Journal of the American Chemical Society in 2021. The article was titled 《Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination》.Recommanded Product: 1-Bromo-3,4,5-trimethoxybenzene The article contains the following contents:

Herein we report the copper-catalyzed silylation of propargylic difluorides to generate axially chiral, tetrasubstituted monofluoroallenes in both good yields (27 examples >80%) and enantioselectivities (82-98% ee). Compared to previously reported synthetic routes to axially chiral allenes (ACAs) from prochiral substrates, a mechanistically distinct reaction has been developed: the enantiodiscrimination between enantiotopic fluorides to set an axial stereocenter. DFT calculations and vibrational CD (VCD) suggest that β-fluoride elimination from an alkenyl copper intermediate likely proceeds through a syn-β-fluoride elimination pathway rather than an anti-elimination pathway. The effects of the C1-sym. Josiphos-derived ligand on reactivity and enantioselectivity were investigated. Not only does this report showcase that alkenyl copper species (like their alkyl counterparts) can undergo β-fluoride elimination, but this elimination can be achieved in an enantioselective fashion. The results came from multiple reactions, including the reaction of 1-Bromo-3,4,5-trimethoxybenzene(cas: 2675-79-8Recommanded Product: 1-Bromo-3,4,5-trimethoxybenzene)

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.Recommanded Product: 1-Bromo-3,4,5-trimethoxybenzene1-Bromo-3,4,5-trimethoxybenzene can be used to synthesize symmetric 3,3′,4,4′,5,5′-hexamethoxydiphenylacetylene via Stille-type coupling with bis-(tributylstannyl)acetylene.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Han, C. Q.; Xia, Y. Y.; Sun, Q.; Zou, Q. G. published their research in Organic Preparations and Procedures International in 2021. The article was titled 《Improved Synthesis of Bepotastine Besilate》.Computed Properties of C6H11BrO2 The article contains the following contents:

Authors have described here improvements in the preparation of bepotastine besilate. The improvements may be suitable for industrial application. The optimized conditions have the advantages of simple operation, minimizing impurities and high yield. In the experiment, the researchers used Ethyl 4-bromobutyrate(cas: 2969-81-5Computed Properties of C6H11BrO2)

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.Computed Properties of C6H11BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Palomino-Ruiz, Lucia; Rodriguez-Gonzalez, Sandra; Fallaque, Joel G.; Marquez, Irene R.; Agrait, Nicolas; Diaz, Cristina; Leary, Edmund; Cuerva, Juan M.; Campana, Araceli G.; Martin, Fernando; Millan, Alba; Gonzalez, M. Teresa published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《Single-Molecule Conductance of 1,4-Azaborine Derivatives as Models of BN-doped PAHs》.Name: 9,10-Dibromoanthracene The article contains the following contents:

The single-mol. conductance of a series of BN-acene-like derivatives has been measured by using scanning tunneling break-junction techniques. A strategic design of the target mols. has allowed us to include azaborine units in positions that unambiguously ensure electron transport through both heteroatoms, which is relevant for the development of customized BN-doped nanographenes. We show that the conductance of the anthracene azaborine derivative is comparable to that of the pristine all-carbon anthracene compound Notably, this heteroatom substitution has also allowed us to perform similar measurements on the corresponding pentacene-like compound, which is found to have a similar conductance, thus evidencing that B-N doping could also be used to stabilize and characterize larger acenes for mol. electronics applications. Our conclusions are supported by state-of-the-art transport calculations In the part of experimental materials, we found many familiar compounds, such as 9,10-Dibromoanthracene(cas: 523-27-3Name: 9,10-Dibromoanthracene)

9,10-Dibromoanthracene(cas: 523-27-3) can be sublimated and oxidized to generate anthraquinone. Soluble in hot benzene and hot toluene, slightly soluble in alcohol, ether and cold benzene, insoluble in water.Name: 9,10-Dibromoanthracene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Lanyon-Hogg, Thomas; Ritzefeld, Markus; Zhang, Leran; Andrei, Sebastian A.; Pogranyi, Balazs; Mondal, Milon; Sefer, Lea; Johnston, Callum D.; Coupland, Claire E.; Greenfield, Jake L.; Newington, Joshua; Fuchter, Matthew J.; Magee, Anthony I.; Siebold, Christian; Tate, Edward W. published an article in 2021. The article was titled 《Photochemical Probe Identification of a Small-Molecule Inhibitor Binding Site in Hedgehog Acyltransferase (HHAT)》, and you may find the article in Angewandte Chemie, International Edition.Synthetic Route of C9H9BrO2 The information in the text is summarized as follows:

The mammalian membrane-bound O-acyltransferase (MBOAT) superfamily is involved in biol. processes including growth, development and appetite sensing. MBOATs are attractive drug targets in cancer and obesity; however, information on the binding site and mol. mechanisms underlying small-mol. inhibition is elusive. This study reports rational development of a photochem. probe to interrogate a novel small-mol. inhibitor binding site in the human MBOAT Hedgehog acyltransferase (HHAT). Structure-activity relationship investigation identified single enantiomer IMP-1575, the most potent HHAT inhibitor reported to-date, and guided design of photocrosslinking probes that maintained HHAT-inhibitory potency. Photocrosslinking and proteomic sequencing of HHAT delivered identification of the first small-mol. binding site in a mammalian MBOAT. Topol. and homol. data suggested a potential mechanism for HHAT inhibition which was confirmed by kinetic anal. Our results provide an optimal HHAT tool inhibitor IMP-1575 (Ki=38 nM) and a strategy for mapping small mol. interaction sites in MBOATs.Benzyl 2-bromoacetate(cas: 5437-45-6Synthetic Route of C9H9BrO2) was used in this study.

Benzyl 2-bromoacetate(cas: 5437-45-6) belongs to benzyl acetate. Benzyl acetate is an aromatic chemical, usually appearing as a clear liquid with a moderate sweet-jasmine fragrance. This compound appears as a component of some of our fragrance blends.Synthetic Route of C9H9BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2022,Patel, Kaushalendra; Lanke, Veeranjaneyulu; Marek, Ilan published an article in Journal of the American Chemical Society. The title of the article was 《Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters》.Application of 7051-34-5 The author mentioned the following in the article:

Organoaluminum species promote a smooth nucleophilic substitution at quaternary C stereocenter of stereodefined polysubstituted cyclopropyl Me phosphate with a complete inversion of configuration, even when more reactive functional groups are present. The regio- and diastereoselectivity of the substitution is attributed to the existence of a bicyclobutonium intermediate. In the experimental materials used by the author, we found (Bromomethyl)cyclopropane(cas: 7051-34-5Application of 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.Application of 7051-34-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2022,Dallavalle, Sabrina; Musso, Loana; Cincinelli, Raffaella; Darwiche, Nadine; Gervasoni, Silvia; Vistoli, Giulio; Guglielmi, Mario B.; La Porta, Ilaria; Pizzulo, Maddalena; Modica, Elisa; Prosperi, Federica; Signorino, Giacomo; Colelli, Fabiana; Cardile, Francesco; Fucci, Alessandra; D’Andrea, Egildo Luca; Riccio, Assunta; Pisano, Claudio published an article in European Journal of Medicinal Chemistry. The title of the article was 《Antitumor activity of novel POLA1-HDAC11 dual inhibitors》.Category: bromides-buliding-blocks The author mentioned the following in the article:

Hybrid mols. targeting simultaneously DNA polymerase α (POLA1) and histone deacetylases (HDACs) were designed and synthesized to exploit a potential synergy of action. Among a library of screened mols., MIR002 and GEM144 showed antiproliferative activity at nanomolar concentrations on a panel of human solid and haematol. cancer cell lines. In vitro functional assays confirmed that these mols. inhibited POLA1 primer extension activity, as well as HDAC11. Mol. docking studies also supported these findings. Mechanistically, MIR002 and GEM144 induced acetylation of p53, activation of p21, G1/S cell cycle arrest, and apoptosis. Oral administration of these inhibitors confirmed their antitumor activity in in vivo models. In human non-small cancer cell (H460) xenografted in nude mice MIR002 at 50 mg/kg, Bid (qd x 5 x 3w) inhibited tumor growth (TGI = 61%). More interestingly, in POLA1 inhibitor resistant cells (H460-R9A), the in vivo combination of MIR002 with cisplatin showed an additive antitumor effect with complete disappearance of tumor masses in two animals at the end of the treatment. Moreover, in two human orthotopic malignant pleural mesothelioma xenografts (MM473 and MM487), oral treatments with MIR002 and GEM144 confirmed their significant antitumor activity (TGI = 72-77%). Consistently with recent results that have shown an inverse correlation between POLA1 expression and type I interferon levels, MIR002 significantly upregulated interferon-α in immunocompetent mice. In addition to this study using Ethyl 5-bromovalerate, there are many other studies that have used Ethyl 5-bromovalerate(cas: 14660-52-7Category: bromides-buliding-blocks) was used in this study.

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.Category: bromides-buliding-blocks

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

In 2022,Kaiyasuan, Chokchai; Somjit, Vetiga; Boekfa, Bundet; Packwood, Daniel; Chasing, Pongsakorn; Sudyoadsuk, Taweesak; Kongpatpanich, Kanokwan; Promarak, Vinich published an article in Angewandte Chemie, International Edition. The title of the article was 《Intrinsic Hole Mobility in Luminescent Metal-Organic Frameworks and Its Application in Organic Light-Emitting Diodes》.Electric Literature of C18H12Br3N The author mentioned the following in the article:

Most metal-organic frameworks (MOFs) lack charge mobility, which is crucial for realizing their use in optoelectronic applications. This work proposes the design of a MOF using triarylamine-based ligands (Zr-NBP) as the lone pair electron spacer to enhance the hole mobility in the MOF while maintaining its luminescent properties. Zr-NBP has strong fluorescence with a good hole mobility of 1.05×10-6 cm2 V-1 s-1, which is comparable to organic materials used in optoelectronic devices. We also employed a Zr-NBP nanofilm in the pure phase as both a non-doped emissive layer and a hole-transporting layer within organic light-emitting diodes (OLEDs). The obtained OLED device produced a bright green light with a low turn-on voltage of 3.9 V. This work presents an advance in developing the electronic properties of MOFs by modifying the chem. properties of its building blocks, and will likely inspire further design of MOF materials as active layers in optoelectronic devices. After reading the article, we found that the author used Tris(4-bromophenyl)amine(cas: 4316-58-9Electric Literature of C18H12Br3N)

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

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of C8H15BrO2In 2018 ,《Design and synthesis of potent dual inhibitors of JAK2 and HDAC based on fusing the pharmacophores of XL019 and vorinostat》 appeared in European Journal of Medicinal Chemistry. The author of the article were Chu-Farseeva, Yu-yi; Mustafa, Nurulhuda; Poulsen, Anders; Tan, Eng Chong; Yen, Jeffrey J. Y.; Chng, Wee Joo; Dymock, Brian W.. The article conveys some information:

Specifically blocking more than one oncogenic pathway simultaneously in a cancer cell with a combination of different drugs is the mainstay of the majority of cancer treatments. Being able to do this via two targeted pathways without inducing side effects through a general mechanism, such as chemotherapy, could bring benefit to patients. In this work we describe a new dual inhibitor of the JAK-STAT and HDAC pathways through designing and developing two types of mol. based on the JAK2 selective inhibitor XL019 and the pan-HDAC inhibitor, vorinostat. Both series of compounds had examples with low nanomolar JAK2 and HDAC1/6 inhibition. In some cases good HDAC1 selectivity was achieved while retaining HDAC6 activity. The observed potency is explained through mol. docking studies of all three enzymes. One example, 69c had 16-25 fold selectivity against the three other JAK-family proteins JAK1, JAK3 and TYK2. A number of compounds had sub-micromolar potencies against a panel of 4 solid tumor cell lines and 4 hematol. cell lines with the most potent compound, 45h, having a cellular IC50 of 70 nM against the multiple myeloma cell line KMS-12-BM. Evidence of both JAK and HDAC pathway inhibition is presented in Hela cells showing that both pathways are modulated. Evidence of apoptosis with two compounds in 4 sold tumor cell lines is also presented. In the part of experimental materials, we found many familiar compounds, such as 8-Bromooctanoic acid(cas: 17696-11-6Synthetic Route of C8H15BrO2)

8-Bromooctanoic acid(cas: 17696-11-6) acid is used in the synthesis of 8-(N-Methyl-4,4′-bipyridinyl)- octanoic acid. 8-Mercaptooctanoic acid was prepared from 8-bromooctanoic acid. And 8-Bromooctanoic Acid is a useful compound for sonodynamic therapy.Synthetic Route of C8H15BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary