Month: December 2022

Pd-catalyzed C-S cyclization via C-H functionalization strategy: access to sulfur-containing benzoheterocyclics was written by Chen, Shihao;Wang, Ming;Jiang, Xuefeng. And the article was included in Chinese Journal of Chemistry in 2018.Recommanded Product: 1-(2-Bromoethyl)-4-methoxybenzene This article mentions the following:

An efficient method was developed for the synthesis of functionalized dihydrobenzothiophenes I [R = H, OMe; R¹ = H, Me, NO₂; R² = H, Me, F; R³ = H, OMe; R⁴ = H; R⁵ = H, Et, Ph; R¹R² = OCH₂O; R⁴R⁵ = (CH₂)₄] and thiochromans II [R⁶ = H, 7-t-Bu, 5-MeO; R⁷ = CO₂Et, C(O)O-i-Pr] via Pd-catalyzed C-H functionalization/C-S cyclization of thioacetates. Mechanistic studies indicated that C-H bond cleavage was involved in the rate-determining step. Furthermore, new pathways for the synthesis of semiconductor materials BTBT and BTT demonstrated the great potential of this protocol. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Recommanded Product: 1-(2-Bromoethyl)-4-methoxybenzene).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) 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. 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.Recommanded Product: 1-(2-Bromoethyl)-4-methoxybenzene

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

α-Cyanostilbene functionalized carbazole derivatives exhibiting dual-state emission and multi-stimuli responsive fluorescent switching was written by Xue, Jie;Tang, Fang;Ding, Aixiang;He, Felicia;Huang, Jianyan;Kong, Lin;Yang, Jiaxiang. And the article was included in Journal of Luminescence in 2022.Application In Synthesis of 1-Bromopyrrolidine-2,5-dione This article mentions the following:

Interest in organic luminescent materials that show strong dual state emission (DSE) in both solution and the solid state is rapidly growing due to their widespread applications. The development of DSE luminogens (DSEgens) with multi-stimuli responsive properties capable of achieving multi-parameter detection in complicated environments remains challenging due to the lack of an explicit mol. design strategy. In this work, we devised and prepared two D-π-A-π-D-structured carbazole derivatives, PY-CZ-Pa and PY-CZ-Ta, with intramol. charge transfer (ICT) characteristics and excellent DSE properties. Both the compounds as fluorescent probes are highly sensitive to trace amount of water and picric acid (PA) in organic solvents. The limits of detection are determined to be 0.016% (PY-CZ-Pa) or 0.040% (PY-CZ-Ta) for water and 320 nM (PY-CZ-Pa) or 538 nM (PY-CZ-Ta) for PA. Moreover, the two compounds exhibit reversible mechanofluorochromism, with spectral shifts of over 24 nm. The results presented in this work suggest that bright DSEgens with multi-stimuli responsive properties are promising materials for applications at both the mol. and aggregated levels. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Application In Synthesis of 1-Bromopyrrolidine-2,5-dione).

1-Bromopyrrolidine-2,5-dione (cas: 128-08-5) 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. 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.Application In Synthesis of 1-Bromopyrrolidine-2,5-dione

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Silver-Catalyzed C-H Trifluoromethylation of Arenes Using Trifluoroacetic Acid as the Trifluoromethylating Reagent was written by Shi, Guangfa;Shao, Changdong;Pan, Shulei;Yu, Jingxun;Zhang, Yanghui. And the article was included in Organic Letters in 2015.Synthetic Route of C9H6BrF3O2 This article mentions the following:

Direct trifluoromethylation of arenes using TFA as the trifluoromethylating reagent was achieved with Ag as the catalyst. This reaction not only provides a new protocol for aryl C-H trifluoromethylation, but the generation of CF₃· from TFA may prove useful in other contexts and could potentially be extended to other trifluoromethylation reactions. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8Synthetic Route of C9H6BrF3O2).

Methyl 4-bromo-3-(trifluoromethyl)benzoate (cas: 107317-58-8) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Synthetic Route of C9H6BrF3O2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Calcium-catalyzed carboarylation of alkynes was written by Fu, Liang;Niggemann, Meike. And the article was included in Chemistry – A European Journal in 2015.Application of 14425-64-0 This article mentions the following:

The first transition-metal-free carboarylation of alkynes with com. and readily available alcs. as alkylating agents was realized in the presence of an environmentally benign calcium catalyst. Thereby, a novel protocol for the one-step synthesis of highly congested, all-carbon tetrasubstituted alkenes, as incorporated in potentially bioactive, complex dihydronaphthalene, chromene and dihydroquinoline structures, e.g., I, was provided. The reaction features an unprecedented, particularly wide substrate scope, good functional-group tolerance and simple exptl. operation under mild reaction conditions. In the experiment, the researchers used many compounds, for example, 1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0Application of 14425-64-0).

1-(2-Bromoethyl)-4-methoxybenzene (cas: 14425-64-0) 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. 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 of 14425-64-0

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Fluorosulfonylation of arenediazonium tetrafluoroborates with Na₂S₂O₅ and N-fluorobenzenesulfonimide was written by Liu, Shuai;Huang, Yangen;Xu, Xiu-Hua;Qing, Feng-Ling. And the article was included in Journal of Fluorine Chemistry in 2020.Application In Synthesis of 3-Bromobenzene-1-sulfonyl fluoride This article mentions the following:

A transition-metal-free Sandmeyer-type fluorosulfonylation reaction has been achieved by the three-component reaction of arenediazonium tetrafluoroborates, Na₂S₂O₅, and N-fluorobenzenesulfonimide (NFSI). The reaction proceeds through a radical tandem process, affording various arenesulfonyl fluorides I (R = 4-Me, 4-OMe, 4-COOEt, etc.) in moderate to high yields. This protocol not only provides a complement to the previous fluorosulfonylation reactions, but also extends the applications of Sandmeyer reaction. In the experiment, the researchers used many compounds, for example, 3-Bromobenzene-1-sulfonyl fluoride (cas: 454-65-9Application In Synthesis of 3-Bromobenzene-1-sulfonyl fluoride).

3-Bromobenzene-1-sulfonyl fluoride (cas: 454-65-9) 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. 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 3-Bromobenzene-1-sulfonyl fluoride

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane tribromide as a regenerable and useful reagent for bromination of phenols under mild conditions was written by Hajipour, Abdol R.;Pourmousavi, Seied A.;Ruoho, Arnold E.. And the article was included in Indian Journal of Chemistry in 2006.Quality Control of 4-Bromo-2-chloro-6-nitrophenol This article mentions the following:

1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octane tribromide was examined over several phenolic compounds under mild conditions. The reaction gives brominated phenols in good to excellent yields. Straightforward work-up of the reaction yields pure products in several cases. In the experiment, the researchers used many compounds, for example, 4-Bromo-2-chloro-6-nitrophenol (cas: 58349-01-2Quality Control of 4-Bromo-2-chloro-6-nitrophenol).

4-Bromo-2-chloro-6-nitrophenol (cas: 58349-01-2) 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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Quality Control of 4-Bromo-2-chloro-6-nitrophenol

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Expanded Azaporphyrins Consisting of Multiple BODIPY Units: Global Aromaticity and High Affinities Towards Alkali Metal Ions was written by Rao, Yutao;Xu, Ling;Zhou, Mingbo;Yin, Bangshao;Osuka, Atsuhiro;Song, Jianxin. And the article was included in Angewandte Chemie, International Edition in 2022.Electric Literature of C4H4BrNO2 This article mentions the following:

The 1-pot self-coupling reaction of 3-amino-5-bromo-BODIPY 9 under Buchwald-Hartwig amination conditions gave nitrogen-bridged cyclic BODIPY tetramer 10, pentamer 11, and hexamer 12. Oxidation of 10, 11, and 12 in the presence of alkali metal ions provided 13, 15, and 16, resp., as the first examples of expanded azaporphyrins possessing more than six pyrrole rings. Curiously, the oxidation even in the absence of alkali metal ions gave the same complexes as a result of spontaneous complexation. 10–12 Showed large association constants (10⁴-10⁶ M^-1) with K⁺ and Na⁺, but the spontaneous complexations were not observed, indicating the extremely high affinities of 13–16 toward alkali metal ions, which can be ascribed to the multiple and effective ion-dipole interaction of the alkali metal ion with the neg. polarized F atoms of the BF₂ walls surrounding the cavity. Importantly, 13, 14, and 15 show diatropic ring currents as a result of global aromaticity. In the experiment, the researchers used many compounds, for example, 1-Bromopyrrolidine-2,5-dione (cas: 128-08-5Electric Literature of C4H4BrNO2).

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. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Electric Literature of C4H4BrNO2

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Micellar Suzuki Cross-Coupling between Thiophene and Aniline in Water and under Air was written by Yousif, Dawod;Tombolato, Silvia;Ould Maina, Elmehdi;Po, Riccardo;Biagini, Paolo;Papagni, Antonio;Vaghi, Luca. And the article was included in Organics in 2021.Formula: C6H5Br2N This article mentions the following:

The Suzuki-Miyaura cross-coupling reaction plays a fundamental role in modern synthetic organic chem., both in academia and industry. For this reason, scientists continue to search for new, more effective, cheaper and environmentally friendly procedures. Recently, micellar synthetic chem. has been demonstrated to be an excellent strategy for achieving chem. transformations in a more efficient way, thanks to the creation of nanoreactors in aqueous environments using selected surfactants. In particular, the cheap and com. available surfactant Kolliphor EL (a polyethoxylated castor oil derivative) has been used with success to achieve metal-catalyzed transformations in water with high yields and short reaction times, with the advantage of using air-sensitive catalysts without the need for inert atm. In this work, the Kolliphor EL methodol. was applied to the Suzuki cross-coupling reaction between thiophene and aniline, using the highly effective catalyst Pd(dtbpf)Cl2. The cross-coupling products were achieved at up to 98% yield, with reaction times of up to only 15 min, working at room temperature and without the need for inert atm. 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. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. 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.Formula: C6H5Br2N

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Highly Active Fe₃O₄@SBA-15@NHC-Pd Catalyst for Suzuki-Miyaura Cross-Coupling Reaction was written by Akkoc, Mitat;Bugday, Nesrin;Altin, Serdar;Ozdemir, Ismail;Yasar, Sedat. And the article was included in Catalysis Letters in 2022.Safety of 4-Bromo-4′-tert-butylbiphenyl This article mentions the following:

A novel Pd-NHC functionalized magnetic Fe₃O₄@SBA-15@NHC-Pd catalyst was synthesized and used as an efficient heterogeneous catalyst in the Suzuki-Miyaura C-C bond formation reactions. The Fe₃O₄@SBA-15@NHC-Pd characterized by X-Ray Diffraction (XRD), XPS, Fourier Transform IR (FTIR) spectroscopy, SEM (SEM), Transmission Electron Microscopy (TEM), Energy Dispersive X-ray anal. (EDX), Thermogravimetric Anal. (TGA), DTA (DTA). The Inductively Coupled Plasma-Optical emission spectroscopy (ICP-OES) anal. was used to determine the exact amount of Pd (0.33 wt%) in Fe₃O₄@SBA-15@NHC-Pd. The TEM images of the catalyst showed the existence of palladium nanoparticles immobilized in the catalyst’s structure, while no reducing agent was used. The NHC moieties in the catalyst structure could be stabilize Pd(0) nanoparticles prevents agglomeration. The magnetic catalyst was effectively used in the Suzuki-Miyaura cross-coupling reaction of substituted phenylboronic acid derivatives with (hetero)aryl bromides in the presence of a potassium carbonate at room temperature in aqueous media and magnetic catalyst could be simply extracted from the reaction mixture by an external magnet. Different aryl bromides were converted to coupled-products Ar¹Ar² [Ar¹ = Ph, 4-MeC₆H₄, 4-MeOC₆H₄, etc.; Ar² = Ph, 2-MeC₆H₄, 1-naphthyl, etc.] in excellent yields with spectacular TOFs values (up to 1,960,339 h-1); in the presence of 1 mg of Fe₃O₄@SBA-15@NHC-Pd catalyst (contains 3.1 x 10-6 mol% Pd) at room temperature in aqueous media. After reusability experiments, it was found that this catalyst was effectively used up to ten times in the reaction with almost consistent catalytic efficiency. A decrease in the activity of the 10th reused catalyst was found as 9%. In the experiment, the researchers used many compounds, for example, 4-Bromo-4′-tert-butylbiphenyl (cas: 162258-89-1Safety of 4-Bromo-4′-tert-butylbiphenyl).

4-Bromo-4′-tert-butylbiphenyl (cas: 162258-89-1) 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. 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.Safety of 4-Bromo-4′-tert-butylbiphenyl

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Design and synthesis of an azobenzene-betaine surfactant for photo-rheological fluids was written by Butler, Calum S. G.;King, Joshua P.;Giles, Luke W.;Marlow, Joshua B.;Vidallon, Mark Louis P.;Sokolova, Anna;de Campo, Liliana;Tuck, Kellie L.;Tabor, Rico F.. And the article was included in Journal of Colloid and Interface Science in 2021.Application of 28322-40-9 This article mentions the following:

Morphol. of surfactant self-assemblies are governed by the intermol. interactions and packing constraints of the constituent mols. Therefore, rational design of surfactant structure should allow targeting of the specific self-assembly modes, such as wormlike micelles (WLMs). By inclusion of an appropriate photo-responsive functionality to a surfactant mol., light-based control of formulation properties without the need for additives can be achieved. A novel azobenzene-containing surfactant was synthesized with the intention of producing photo-responsive wormlike micelles. Aggregation of the mol. in its cis and trans isomers, and its concomitant flow properties, were characterised using UV-vis spectroscopy, small-angle neutron scattering, and rheol. measurements. Finally, the fluids capacity for mediating particle diffusion was assessed using dynamic light scattering. The trans isomer of the novel azo-surfactant was found to form a viscoelastic WLM network, which transitioned to inviscid ellipsoidal aggregates upon photo-switching to the cis isomer. This was accompanied by changes in zero-shear viscosity up to 16,000 x . UV-vis spectroscopic and rheo-SANS anal. revealed π – π interactions of the trans azobenzene chromophore within the micelles, influencing aggregate structure and contributing to micellar rigidity. Particles dispersed in a 1 wt% surfactant solution showed a fivefold increase in apparent diffusion coefficient after UV-irradiation of the mixture In the experiment, the researchers used many compounds, for example, Isopentyltriphenylphosphonium bromide (cas: 28322-40-9Application of 28322-40-9).

Isopentyltriphenylphosphonium bromide (cas: 28322-40-9) 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. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Application of 28322-40-9

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary