Bromides-buliding-blocks

A highly practical and convenient halogenation of fused heterocyclic N-oxides was written by Wang, Dong;Wang, Yuxi;Zhao, Junjie;Li, Linna;Miao, Longfei;Wang, Dong;Sun, Hua;Yu, Peng. And the article was included in Tetrahedron in 2016.Synthetic Route of C12H7BrN2 This article mentions the following:

A novel, simple and practical method for the regioselective halogenation of fused heterocyclic N-oxides was developed. It employs Vilsmeier reagent, generated in situ by POX₃ and DMF, as both the activating agent and the nucleophilic halide source. The method is amenable across a broad range of substrates, including quinolines, isoquinolines and the diazine N-oxides, possessing a variety of substitution patterns. Furthermore, all of the reagents associated are cheap and easy to obtain. The potential extension of this method to a one-pot oxidation/halogenation sequence that obviates the need for isolation of the N-oxide intermediates is also presented. In the experiment, the researchers used many compounds, for example, 2-Bromo-1,10-phenanthroline (cas: 22426-14-8Synthetic Route of C12H7BrN2).

2-Bromo-1,10-phenanthroline (cas: 22426-14-8) belongs to organobromine compounds. 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. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Synthetic Route of C12H7BrN2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Evidence of an Odorant-Binding Protein in the Human Olfactory Mucus: Location, Structural Characterization, and Odorant-Binding Properties was written by Briand, Loiec;Eloit, Corinne;Nespoulous, Claude;Bezirard, Valerie;Huet, Jean-Claude;Henry, Celine;Blon, Florence;Trotier, Didier;Pernollet, Jean-Claude. And the article was included in Biochemistry in 2002.Computed Properties of C15H29BrO2 This article mentions the following:

Odorant-binding proteins (OBPs) are small abundant extracellular proteins belonging to the lipocalin superfamily. They are thought to participate in perireceptor events of odor detection by carrying, deactivating, and/or selecting odorant mols. Putative human OBP genes (hOBP) have recently been described [Lacazette et al. (2000) Hum. Mol. Genet. 9, 289-301], but the presence of the corresponding proteins remained to be established in the human olfactory mucus. This paper reports the first evidence of such expression in the mucus covering the olfactory cleft, where the sensory olfactory epithelium is located. On the contrary, hOBPs were not observed in the nasal mucus covering the septum and the lower turbinate. To demonstrate the odorant binding activity of these proteins, a corresponding recombinant protein variant, hOBP_{IIa浼?/sub>, was secreted by the yeast Pichia pastoris and thoroughly characterized. It appears as a monomer with one disulfide bond located between C59 and C151, a conservative feature of all other vertebrate OBPs. By measuring the displacement of several fluorescent probes, we show that hOBPIIa浼?/sub> is able to bind numerous odorants of diverse chem. structures, with a higher affinity for aldehydes and large fatty acids. A computed 3D model of hOBPIIa浼?/sub> is proposed and reveals that two lysyl residues of the binding pocket may account for the increased affinity for aldehydes. The relatively limited specificity of hOBPIIa浼?/sub> suggests that other human OBPs are expected to take into account the large diversity of odorant mols. In the experiment, the researchers used many compounds, for example, 15-Bromopentadecanoic acid (cas: 56523-59-2Computed Properties of C15H29BrO2).}

15-Bromopentadecanoic acid (cas: 56523-59-2) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbon鑱砨romine bond is electrophilic in nature. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Computed Properties of C15H29BrO2

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Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of phthalonitriles using a palladium catalyst was written by Iqbal, Zafar;Lyubimtsev, Alexey;Hanack, Michael. And the article was included in Synlett in 2008.Formula: C6H5Br2N This article mentions the following:

An easy synthetic method to obtain phthalonitriles from o-dibromobenzenes under mild conditions in high yields using Zn(CN)₂ and a catalytic amount of tris(dibenzylideneacetone)dipalladium and 1,1′-bis(diphenylphosphino)ferrocene is described. In the experiment, the researchers used many compounds, for example, 3,4-Dibromoaniline (cas: 615-55-4Formula: C6H5Br2N).

3,4-Dibromoaniline (cas: 615-55-4) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Formula: C6H5Br2N

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Schiff bases formed between pyridoxal 5′-phosphate and amino-灏?cyclodextrins: intramolecular remote ion pair interactions of the phosphate with ammonium moieties was written by Tamagaki, Seizo;Takahashi, Masahiko;Kanamori, Junji;Tagaki, Waichiro. And the article was included in Supramolecular Chemistry in 1994.Name: Heptakis(6-Bromo-6-Deoxy)-灏?Cyclodextrin This article mentions the following:

Equilibrium involved in the Schiff base formations of pyridoxal 5′-phosphate (PLP) and 5′-deoxypyridoxal with mono-, di-, and peraminocyclodextrins have been studied to determine equilibrium binding constants in aqueous media at several pH values. These results, as well as the CD study, show that remote electrostatic interactions between the neg. charged 5′-phosphate group and a second ammonium group on the cyclodextrins play a significant role in the complexation. In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-灏?Cyclodextrin (cas: 53784-83-1Name: Heptakis(6-Bromo-6-Deoxy)-灏?Cyclodextrin).

Heptakis(6-Bromo-6-Deoxy)-灏?Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. 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: Heptakis(6-Bromo-6-Deoxy)-灏?Cyclodextrin

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Bromide – Wikipedia,
bromide – Wiktionary

Tuning the activity of known drugs via the introduction of halogen atoms, a case study of SERT ligands – Fluoxetine and fluvoxamine was written by Staron, Jakub;Pietrus, Wojciech;Bugno, Ryszard;Kurczab, Rafal;Satala, Grzegorz;Warszycki, Dawid;Lenda, Tomasz;Wantuch, Anna;Hogendorf, Adam S.;Hogendorf, Agata;Duszynska, Beata;Bojarski, Andrzej J.. And the article was included in European Journal of Medicinal Chemistry in 2021.Recommanded Product: 4457-67-4 This article mentions the following:

To elucidate the role of halogen atoms in the binding of SSRIs to SERT, a series of 22 fluoxetine and fluvoxamine analogs substituted with fluorine, chlorine, bromine, and iodine atoms, differently arranged on the Ph ring was designed. The obtained biol. activity data, supported by a thorough in silico binding mode anal., allowed the identification of two partners for halogen bond interactions: the backbone carbonyl oxygen atoms of E493 and T497. Addnl., compounds with heavier halogen atoms were found to bind with the SERT via a distinctly different binding mode, a result not presented elsewhere. The subsequent anal. of the prepared XSAR sets showed that E493 and T497 participated in the largest number of formed halogen bonds. The XSAR library anal. led to the synthesis of two of the most active compounds (3,4-diCl-fluoxetine, SERT K_i = 5 nM and 3,4-diCl-fluvoxamine, SERT K_i = 9 nM, fluoxetine SERT K_i = 31 nM, fluvoxamine SERT K_i = 458 nM). An example of the successful use of a rational methodol. was presented to analyze binding and design more active compounds by halogen atom introduction. ‘XSAR library anal.’, a new tool in medicinal chem., was instrumental in identifying optimal halogen atom substitution. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Recommanded Product: 4457-67-4).

1-Bromo-4-methoxybutane (cas: 4457-67-4) 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. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Recommanded Product: 4457-67-4

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Bromide – Wikipedia,
bromide – Wiktionary

2-Substituted-3H-indol-3-one-1-oxides: Preparation and radical trapping properties was written by Boyer, Jeremie;Bernardes-Genisson, Vania;Farines, Vincent;Souchard, Jean-Pierre;Nepveu, Francoise. And the article was included in Free Radical Research in 2004.Computed Properties of C23H26BrP This article mentions the following:

2-Alkyl and 2-aryl substituted-3H-indol-3-one-1-oxides were prepared and evaluated for their radical trapping properties. Spin trapping and ESR experiments demonstrate the ability of these indolone-1-oxides to trap hetero- and C-centered radicals. The most stable spin adducts (lifetime of several hours) were obtained with 2-alkyl substituted nitrones, e.g. 6-ethyl-7H-[1,3]dioxolo[4,5-f]indol-7-one 5-oxide and 2-isobutyl-3H-indol-3-one 1-oxide. These two nitrones are also sensitive to redox reactions in solution Therefore this indolone-1-oxide series lacking a 灏?H atom gives rise to highly stable adducts with free radicals. In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Computed Properties of C23H26BrP).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) 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. Bromine-containing agents predominate because not only are they more efficient than similar chlorine-containing species, but also the high atomic weight of bromine ensures that it is present in a high mass fraction within most organobromine compounds.Computed Properties of C23H26BrP

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Bromide – Wikipedia,
bromide – Wiktionary

An integration of condensation/Ullmann-type coupling/bicyclization sequences: copper-catalyzed three-component direct synthesis of [1,2,4]triazolo[1,5-b]isoquinolin-5(1H)-ones was written by Jia, Feng-Cheng;Xu, Cheng;Cai, Qun;Wu, An-Xin. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2014.SDS of cas: 653-92-9 This article mentions the following:

A highly efficient three-component domino protocol has been developed for the synthesis of [1,2,4]triazolo[1,5-b]isoquinolin-5(1H)-ones from simple and readily available o-halogenated benzohydrazides, aldehydes and nitriles. This domino process involves sequential selective condensation, copper-catalyzed intermol. C-arylation and bicyclization. Notably, the use of ligands and anaerobic conditions can be avoided in this reaction. In the experiment, the researchers used many compounds, for example, Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9SDS of cas: 653-92-9).

Methyl 2-bromo-4-fluorobenzoate (cas: 653-92-9) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. SDS of cas: 653-92-9

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Bromide – Wikipedia,
bromide – Wiktionary

Oxacyclanes was written by Kirrmann, A.;Hamaide, N.. And the article was included in Bulletin de la Societe Chimique de France in 1957.Quality Control of 1-Bromo-6-methoxyhexane This article mentions the following:

Oxacyclanes were formed by heating 绾? 鏈? or 钄?methoxylated alkyl bromides with FeCl₃. NaOMe (1 mole) in MeOH added slowly with stirring to 1 mole dibromoalkane at 60鎺? the mixture boiled gently 4 hrs. and cooled, the washed and dried product distilled, and the bromo methoxy alkane fraction carefully redistilled in vacuo gave MeO(CH₂)₆Br, b₁₄ 94鎺? n_D²⁰ 1.458, d₂₀ 1.1942, MeCH(OMe)CH₂CH₂CHBrMe, b₃₅ 100鎺? n_D²⁰ 1.441, d₂₀1.1824, MeO(CH₂)₅Br, b₁₅ 76鎺? n_D²⁰ 1.455, d₂₀ 1.2420, and MeO(CH₂)₄Br (I), b₁₅ 60鎺? n_D²⁰ 1.452, d₂₀ 1.3052, in 56, 53, 55, and 57% yields, resp. Regulated mild distillation of these products in the presence of a few mg. FeCl₃ gave the oxacyclanes (compound, % yield, b.p., n_D²⁰, d₂₀, 浣?in 娓?: tetrahydrofuran, 100, 67鎺? 1.407, 0.8874, 3.34, 6.85, 9.34; tetrahydropyran, 100, 88鎺? 1.4205, 0.8851, 3.30, 6.92, 9.12, 11.46, 12.26; hexamethylene oxide, 70, 116鎺? 1.4355, 0.895, 3.42, 6.90, 8.80, 9.02, 10.04, 10.30, 12.22, 12.44; 2,5-dimethyltetrahydrofuran, 80, 96鎺? 1.410, 0.8373, 3.3, 6.8, 7.2, 9.1, 11.3, 11.94, 12.1. The MeBr formed in the cyclization of I was condensed at -15鎺?with anhydrous Et₂O and Mg, the MeMgBr treated with BzH and the MePhCHOH formed identified as the phenylurethan. The mechanism of the reaction was interpreted through the intermediary formation of a tertiary oxonium salt. In the experiment, the researchers used many compounds, for example, 1-Bromo-6-methoxyhexane (cas: 50592-87-5Quality Control of 1-Bromo-6-methoxyhexane).

1-Bromo-6-methoxyhexane (cas: 50592-87-5) belongs to organobromine compounds. 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. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Quality Control of 1-Bromo-6-methoxyhexane

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Syntheses of polyfunctionalized resveratrol derivatives using Wittig and Heck protocols was written by Chalal, Malik;Vervandier-Fasseur, Dominique;Meunier, Philippe;Cattey, Helene;Hierso, Jean-Cyrille. And the article was included in Tetrahedron in 2012.Name: 5-Bromo-2-(hydroxymethyl)phenol This article mentions the following:

Improved protocols for Wittig reaction and palladium-catalyzed Heck coupling give expedient access to a series of unprecedented polyfunctionalized artificial-resveratrol derivatives, e.g., I. In the modified Wittig protocol, trimethylsilyl was used as a highly valuable protective group of the phenolic functions of starting aromatic materials. A clean O-alkylation of hydroxylated stilbenes with ethylene carbonate was also conducted. Thus, Wittig reaction followed by hydroxyethylation take place one-pot with only carbon dioxide as waste. Addnl., a palladium-catalyzed Heck coupling strategy was developed by using ferrocenyl phosphane ligands, and multi-functionalized hydroxylated stilbenes were obtained without the need of any protection/deprotection sequence. Up to six functional groups are introduced by these procedures, which limit the number of reaction steps, the waste toxicity, and the use of costly reagents. In the experiment, the researchers used many compounds, for example, 5-Bromo-2-(hydroxymethyl)phenol (cas: 170434-11-4Name: 5-Bromo-2-(hydroxymethyl)phenol).

5-Bromo-2-(hydroxymethyl)phenol (cas: 170434-11-4) belongs to organobromine compounds. 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Name: 5-Bromo-2-(hydroxymethyl)phenol

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Bromide – Wikipedia,
bromide – Wiktionary

Multichromophoric cyclodextrins. 1. Synthesis of O-naphthoyl-灏?cyclodextrins and investigation of excimer formation and energy hopping was written by Berberan-Santos, Mario N.;Canceill, Josette;Brochon, Jean Claude;Jullien, Ludovic;Lehn, Jean Marie;Pouget, Jacques;Tauc, Patrick;Valeur, Bernard. And the article was included in Journal of the American Chemical Society in 1992.Formula: C42H63Br7O28 This article mentions the following:

The synthesis and photophys. properties of 灏?cyclodextrins bearing seven 2-naphthoyloxy chromophores in specific positions, either on the primary face or the secondary face, or 14 naphthoyloxy chromophores, seven on each face, are reported. These multichromophoric cyclodextrins are good models for the study of excitation energy migration among chromophores in well-defined positions. The investigation was performed in CH₂Cl₂ and in a mixture of EtOH and MeOH that can form in a glass at low temperature The absorption spectra show that the interactions between chromophores in the ground state are weak, whereas the fluorescence spectra reveal the existence of excimers at room temperature but not at low temperature in a rigid glass. Further evidence of excimer formation is provided by the fluorescence decays. Since excimers act as energy traps, the energy hopping process was studied in a rigid glass at low temperature by steady-state and time-resolved fluorescence depolarization techniques. The steady-state anisotropy is found to be one seventh of the theor. limiting anisotropy 0.4, which means that excitation energy hops between chromophores with essentially randomly oriented transition moments at a rate much higher than the chromophore intrinsic decay rate. Energy hopping is indeed very fast as shown by the fluorescence anisotropy decay which is at least as fast as the apparatus time resolution (a few tens of picoseconds). In the experiment, the researchers used many compounds, for example, Heptakis(6-Bromo-6-Deoxy)-灏?Cyclodextrin (cas: 53784-83-1Formula: C42H63Br7O28).

Heptakis(6-Bromo-6-Deoxy)-灏?Cyclodextrin (cas: 53784-83-1) belongs to organobromine compounds. Bromo compounds are employed in a variety of metal-catalyzed coupling reactions. They are also ideal candidates for the synthesis of Grignard reagents that have wide-applicability in organic synthesis. alpha-Bromoesters are employed in the Reformatsky reaction for the synthesis of beta-hydroxyesters. The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Formula: C42H63Br7O28

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary