Category: bromides-buliding-blocks

Characterization of a chemosensory protein (ASP3c) from honeybee (Apis mellifera L.) as a brood pheromone carrier was written by Briand, Loic;Swasdipan, Nicharat;Nespoulous, Claude;Bezirard, Valerie;Blon, Florence;Huet, Jean-Claude;Ebert, Paul;Pernollet, Jean-Claude. And the article was included in European Journal of Biochemistry in 2002.Synthetic Route of C15H29BrO2 This article mentions the following:

We report the cloning of a honeybee chemosensory proteins (CSP) gene called ASP3c, as well as the structural and functional characterization of the encoded protein. The protein was heterologously secreted by the yeast Pichia pastoris using the native signal peptide. ASP3c disulfide bonds were assigned after trypsinolysis followed by chromatog. and mass spectrometry combined with microsequencing. The pairing (Cys(I)-Cys(II), Cys(III)-Cys(IV)) was found to be identical to that of Schistocerca gregaria CSPs, suggesting that this pattern occurs commonly throughout the insect CSPs. CD measurements revealed that ASP3c mainly consists of α-helixes, like other insect CSPs. Gel filtration anal. showed that ASP3c is monomeric at neutral pH. Using ASA, a fluorescent fatty acid anthroyloxy analog as a probe, ASP3c was shown to bind specifically to large fatty acids and ester derivatives, which are brood pheromone components, in the micromolar range. It was unable to bind tested general odorants and other tested pheromones (sexual and nonsexual). This is the 1st report on a natural pheromonal ligand bound by a recombinant CSP with a measured affinity constant In the experiment, the researchers used many compounds, for example, 15-Bromopentadecanoic acid (cas: 56523-59-2Synthetic Route 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–bromine bond is electrophilic in nature. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Synthetic Route of C15H29BrO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis of a metabolically stable modified long-chain fatty acid salt and its photolabile derivative was written by Stoll, G. H.;Voges, R.;Gerok, W.;Kurz, G.. And the article was included in Journal of Lipid Research in 1991.Recommanded Product: 15-Bromopentadecanoic acid This article mentions the following:

An analog of the long-chain fatty acid salt, sodium stearate, was synthesized in which the H atoms at carbons 2, 3, and 18 were replaced by fluorine. The key step in the synthesis was the addition of 3-iodo-2,2,3,3-tetrafluoropropanoic acid amide to 15,15,15-trifluoro-1-pentadecene. Radioactivity was introduced by catalytic reduction of 2,2,3,3,18,18,18-heptafluoro-4-octadecenoic acid amide with carrier-free tritium gas yielding a product with the specific radioactivity of 2.63 TBq/mmol. The resulting 2,2,3,3,18,18,18-heptafluoro-4-octadecenoic acid has a pK_a of about 0.5 and is completely dissociated under normal physiol. conditions. The fluorinated fatty acid salt analog is readily taken up into hepatocytes and proved to be metabolically inert. In an approach to the identification of proteins involved in long-chain fatty acid salt transport across membranes and intracellular compartments, the photolabile derivative 11,11-azo-2,2,3,3,18,18,18-heptafluoro[G–³H]octadecanoic acid sodium salt was synthesized with a specific radioactivity of 2.63 TBq/mmol. Photolysis of the photolabile derivative, using a light source with a maximum emission at 350 nm, occurred with a half-life of 1.5 min. The generated carbene reacted with ¹⁴C-labeled MeOH and MeCN with covalent bond formation of 6-13%. Its efficacy for photoaffinity labeling was demonstrated by incorporation into serum albumin, the extracellular fatty acid salt-binding protein, as well as into the intracellular fatty acid salt-binding protein (FABP) of rat liver with mol. weight of 14,000. In the experiment, the researchers used many compounds, for example, 15-Bromopentadecanoic acid (cas: 56523-59-2Recommanded Product: 15-Bromopentadecanoic acid).

15-Bromopentadecanoic acid (cas: 56523-59-2) belongs to organobromine compounds. 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. 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: 15-Bromopentadecanoic acid

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Halide Perovskite Cluster Precursors: A Paradigm for Obtaining Structure- and Color-Tunable Light-Emitting Nanocrystals was written by Dutta, Sumit Kumar;Peng, Lucheng;Hudait, Biswajit;Xie, Renguo;Pradhan, Narayan. And the article was included in ACS Energy Letters in 2022.SDS of cas: 128-08-5 This article mentions the following:

The compositions of precursors during the syntheses of CsPbX₃ nanocrystals typically determine the resulting crystal phase and stability. Different precursors providing single or multiple constituent ions have already been developed for tuning the reaction pathways for architecting different sizes and shapes of such nanocrystals. Among these, the CsPbBr₃ clusters, composed of Cs, Pb, and Br, as well as limited ligands, employed as single-source precursors, provide an ideal pathway for obtaining a wide window of size/shape-tunable CsPbBr₃ nanocrystals. Recent reports also revealed that this pathway can lead to the epitaxial growth of non-perovskite nanostructures on perovskite nanocrystals. Further, the limited ligands here helped in shape modulation by opening different facets and also triggering facet directed connections of the nanocrystals. Keeping those in mind, the importance of these unique cluster precursors for the development of halide perovskite nanocrystals and their heterostructures is discussed, and possibilities for their utilization in different unexplored areas of research are proposed in this Perspective. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5SDS of cas: 128-08-5).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.SDS of cas: 128-08-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tricyclic pharmacophore-based molecules as novel integrin α_vβ₃ antagonists. Part IV: Preliminary control of α_vβ₃ selectivity by meta-oriented substitution was written by Kubota, Dai;Ishikawa, Minoru;Ishikawa, Midori;Yahata, Naokazu;Murakami, Shoichi;Fujishima, Kazuyuki;Kitakaze, Masafumi;Ajito, Keiichi. And the article was included in Bioorganic & Medicinal Chemistry in 2006.Application of 82702-31-6 This article mentions the following:

To establish the in vivo efficacy of α_vβ₃/α_IIbβ₃ dual antagonists possessing a tricyclic pharmacophore, a corresponding α_vβ₃-selective antagonist was required as a control. We initially took two synthetic approaches to obtain α_vβ₃-selective antagonists based on the RGD recognition pattern or on modification of the dihedral angle between the central benzene ring and the adjacent heterocycle, but both proved unsuccessful. However, synthesis of novel antagonists with meta-substitution of the central benzene ring generated weak selectivity for α_vβ₃ over α_IIbβ₃ for the first time in the family of compounds with the tricyclic pharmacophore. Optimization of meta-oriented antagonists furnished an α_vβ₃-selective antagonist exhibiting inhibitory activity not only in a receptor-binding assay, but also in a cell adhesion assay. In the experiment, the researchers used many compounds, for example, Methyl 3-bromo-4-fluorobenzoate (cas: 82702-31-6Application of 82702-31-6).

Methyl 3-bromo-4-fluorobenzoate (cas: 82702-31-6) 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.Application of 82702-31-6

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

S_N2 Substitution Reactions at the Amide Nitrogen in the Anomeric Mutagens, N-Acyloxy-N-alkoxyamides was written by Cavanagh, Katie L.;Glover, Stephen A.;Price, Helen L.;Schumacher, Rhiannon R.. And the article was included in Australian Journal of Chemistry in 2009.Application In Synthesis of 2-(Bromomethyl)-1,3-dimethylbenzene This article mentions the following:

N-Acyloxy-N-alkoxyamides 1a are unusual anomeric amides that are pyramidal at the nitrogen because of bis oxyl substitution. Through this configuration, they lose most of their amide character and resemble α-haloketones in reactivity. They are susceptible to S_N2 reactions at nitrogen, a process that is responsible for their mutagenic behavior. Kinetic studies have been carried out with the nucleophile N-methylaniline that show that, like S_N2 reactions at carbon centers, the rate constant for S_N2 displacement of carboxylate is lowered by branching β to the nitrogen center, or bulky groups on the alkoxyl side chain. Branching or bulky groups on the carboxylate leaving group, however, do not impact on the rate of substitution, which is mostly controlled by the pK_A of the departing carboxylate group. These results are in line with computed properties for the model reaction of ammonia with N-acetoxy-N-methoxyacetamide but are in contrast to the role of steric effects on their mutagenicity. In the experiment, the researchers used many compounds, for example, 2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7Application In Synthesis of 2-(Bromomethyl)-1,3-dimethylbenzene).

2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7) 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). 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.Application In Synthesis of 2-(Bromomethyl)-1,3-dimethylbenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Synthesis, properties and antimicrobial activity of 5-trifluoromethyl-2-formylphenylboronic acid was written by Adamczyk-Wozniak, Agnieszka;Gozdalik, Jan T.;Wieczorek, Dorota;Madura, Izabela D.;Kaczorowska, Ewa;Brzezinska, Ewa;Sporzynski, Andrzej;Lipok, Jacek. And the article was included in Molecules in 2020.Application In Synthesis of 2-Bromo-4-(trifluoromethyl)benzaldehyde This article mentions the following:

2-Formylphenylboronic acids display many interesting features, not only from synthetic but also from an application as well as structural points of view. 5-Trifluoromethyl-2-formyl phenylboronic acid has been synthesized and characterized in terms of its structure and properties. The presence of an electron-withdrawing substituent results in a considerable rise in the acidity in comparison with its analogs. Taking into account the probable mechanism of antifungal action of benzoxaboroles, which blocks the cytoplasmic leucyl-tRNA synthetase (LeuRS) of the microorganism, docking studies with the active site of the enzymes have been carried out. It showed possible binding of the cyclic isomer into the binding pocket of Candida albicans LeuRS, similar to that of the recently approved benzoxaborole antifungal drug (AN2690, Tavaborole, Kerydin). In case of Escherichia coli LeuRS, the opened isomer displays a much higher inhibition constant in comparison with the cyclic one. The antimicrobial activity of the title compound was also investigated in vitro, showing moderate action against Candida albicans. The compound reveals higher activity against Aspergillus niger as well as bacteria such as Escherichia coli and Bacillus cereus. In case of Bacillus cereus, the determined Min. Inhibitory Concentration (MIC) value is lower than that of AN2690 (Tavaborole). The results confirm potential of 2-formylphenylboronic acids as antibacterial agents and give a hint of their possible mechanism of action. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Application In Synthesis of 2-Bromo-4-(trifluoromethyl)benzaldehyde).

2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) belongs to organobromine compounds. 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. 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.Application In Synthesis of 2-Bromo-4-(trifluoromethyl)benzaldehyde

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Screening of a virtual mirror-image library of natural products was written by Noguchi, Taro;Oishi, Shinya;Honda, Kaori;Kondoh, Yasumitsu;Saito, Tamio;Ohno, Hiroaki;Osada, Hiroyuki;Fujii, Nobutaka. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2016.Application In Synthesis of Isopentyltriphenylphosphonium bromide This article mentions the following:

We established a facile access to an unexplored mirror-image library of chiral natural product derivatives using D-protein technol. In this process, two chem. syntheses of mirror-image substances including a target protein and hit compound(s) allow the lead discovery from a virtual mirror-image library without the synthesis of numerous mirror-image compounds In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Application In Synthesis of Isopentyltriphenylphosphonium bromide).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) 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–bromine bond is electrophilic in nature. 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.Application In Synthesis of Isopentyltriphenylphosphonium bromide

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Sc(OTf)₃-Mediated [4 + 2] Annulations of N-Carbonyl Aryldiazenes with Cyclopentadiene to Construct Cinnoline Derivatives: Azo-Povarov Reaction was written by Jimenez-Aberasturi, Xabier;Palacios, Francisco;de los Santos, Jesus M.. And the article was included in Journal of Organic Chemistry in 2022.Name: 1-Bromopyrrolidine-2,5-dione This article mentions the following:

The first accomplishment of the azo-Povarov reaction involving Sc(OTf)₃-catalyzed [4 + 2] annulations of N-carbonyl aryldiazenes with cyclopentadiene in chloroform, in which N-carbonyl aryldiazenes act as 4π-electron donors. Hence, this protocol offer a rapid access to an array of cinnoline derivatives in moderate to good yields for substrates over a wide scope. The synthetic potential of the protocol was achieved by the gram-scale reaction and further derivatization of the obtained polycyclic product. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Name: 1-Bromopyrrolidine-2,5-dione).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) 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. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.Name: 1-Bromopyrrolidine-2,5-dione

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design, synthesis and structure of new potential electrochemically active boronic acid-based glucose sensors was written by Norrild, Jens Chr.;Sotofte, Inger. And the article was included in Journal of the Chemical Society, Perkin Transactions 2 in 2002.HPLC of Formula: 166821-88-1 This article mentions the following:

In the authors’ studies on new boronic acid based carbohydrate sensors three new boronic acids (2-FcCH₂NMeCH₂C₆H₄B(OH)₂ (3), 1,2-(2-(HO)₂BC₆H₄CH₂NMeCH₂)₂ferrocene (7) and 1,1′-(2-(HO)₂BC₆H₄CH₂NMeCH₂)₂ferrocene (11)) containing a ferrocene moiety were synthesized. Their design includes an intramol. B-N bonding motif to facilitate binding at physiol. pH. The authors report the synthesis of the compounds and studies on glucose complexation as studied by ¹³C NMR spectroscopy. The crystal structure of 2,4,6-tris[2-(N-ferrocenylmethyl-N-methylaminomethyl)phenyl]boroxin (13) (boroxin of boronic acid 3) (boroxin = cyclotriboroxane) was obtained and compared with structures obtained of 2,4,6-tris[2-(N,N-dimethylaminomethyl)phenyl]boroxin (14) and 2-(2-(dimethylaminomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (15). The structure of 13 shows the existence of intramol. B-N bonds in the solid phase. In the experiment, the researchers used many compounds, for example, 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1HPLC of Formula: 166821-88-1).

2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1) 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. 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.HPLC of Formula: 166821-88-1

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Deoxofluorination of (Hetero)aromatic Acids was written by Trofymchuk, Serhii;Bugera, Maksym Ya.;Klipkov, Anton A.;Razhyk, Bohdan;Semenov, Sergey;Tarasenko, Karen;Starova, Viktoriia S.;Zaporozhets, Olga A.;Tananaiko, Oksana Yu.;Alekseenko, Anatoliy N.;Pustovit, Yurii;Kiriakov, Oleksandr;Gerus, Igor I.;Tolmachev, Andrei A.;Mykhailiuk, Pavel K.. And the article was included in Journal of Organic Chemistry in 2020.Reference of 29241-66-5 This article mentions the following:

Diverse trifluoromethyl-substituted compounds were synthesized by deoxofluorination of cinnamic and (hetero)aromatic carboxylic acids with sulfur tetrafluoride. The obtained products were used as starting materials in the preparation of novel fluorinated amino acids, anilines, and aliphatic amines – valuable building blocks for medicinal chem. and agrochem. Of note, sulfur tetrafluoride (SF4) and hydrogen fluoride (HF) are toxic, therefore, safety and addnl. tech. training must be taken before working with them. In the experiment, the researchers used many compounds, for example, 5-Bromo-2-fluoronicotinic acid (cas: 29241-66-5Reference of 29241-66-5).

5-Bromo-2-fluoronicotinic acid (cas: 29241-66-5) 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. 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.Reference of 29241-66-5

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary