93-52-7Relevant academic research and scientific papers
Reactive separation of β-bromoethylbenzene from α-β-bromoethylbenzene mixtures: a Zn2+-mediated radical polymerization mechanism
Deng, Tianyu,Tian, Jiaming,Yan, Binhang,Zhu, Junqiu
, p. 1219 - 1222 (2022/02/03)
A Zn2+-induced reactive separation method for the purification of β-bromoethylbenzene from α-β-bromoethylbenzene mixtures is discovered, where the selective decomposition of α-bromoethylbenzene follows a radical mechanism. Zn2+ facilitates the homolysis of the C-Br bond of halohydrocarbons with benzyl bromide, enabling the separation of the corresponding isomers with almost identical physical properties.
Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide
Kumaki, Wataru,Kinoshita, Hidenori,Miura, Katsukiyo
supporting information, (2022/03/07)
Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.
A General Method for the Dibromination of Vicinal sp3C-H Bonds Exploiting Weak Solvent-Substrate Noncovalent Interactions
Qi, Zaojuan,Li, Weihe,Niu, Yanning,Benassi, Enrico,Qian, Bo
supporting information, p. 2399 - 2404 (2021/03/03)
A general procedure of 1,2-dibromination of vicinal sp3 C-H bonds of arylethanes using N-bromosuccinimide as the bromide reagent without an external initiator has been established. The modulation of the strength of the intermolecular noncovalent interactions between the solvent and arylethane ethanes, quantitatively evaluated via quantum chemical calculations, allows us to circumvent the fact that arylethane ethane cannot be dibrominated through traditional methods. The mechanism was explored by both experiments and quantum chemical calculations, revealing a radical chain with HAA process.
Electrochemical bromofunctionalization of alkenes in a flow reactor
Seitz, Jakob,Wirth, Thomas
supporting information, p. 6892 - 6896 (2021/08/20)
The bromination of organic molecules has been extensively studied to date, yet there is still a demand for safe and sustainable methodologies. Hazardous reagents, selectivity, low atom economy and waste production are the most persisting problems of brominating reagents. The electrochemical oxidation of bromide to bromine is a viable strategy to reduce waste by avoiding chemical oxidants. Furthermore, thein situgeneration of reactive intermediates minimizes the risk of hazardous reagents. In this work, we investigate the electrochemical generation of bromine from hydrobromic acid in a flow electrochemical reactor. Various alkenes could be converted to their corresponding dibromides, bromohydrines, bromohydrin ethers and cyclized products in good to excellent yields.
Emergent Self-Assembly of a Multicomponent Capsule via Iodine Capture
Yang, Yu-Dong,Chen, Xu-Lang,Sessler, Jonathan L.,Gong, Han-Yuan
supporting information, p. 2315 - 2324 (2021/01/13)
Described here is a three-component self-assembly system that displays emergent behavior that differs from that of its constituents. The system comprises an all-hydrocarbon octaaryl macrocycle cyclo[8](1,3-(4,6-dimethyl)benzene (D4d-CDMB-8), corannulene (Cora), and I2. No appreciable interaction is seen between any pair of these three-components, either in cyclohexane or under various crystallization conditions. On the other hand, when all three-components are mixed in cyclohexane and allowed to undergo crystallization, a supramolecular iodine-containing capsule, ((D4d-CDMB-8)3(Cora)2)I2, is obtained. This all-hydrocarbon capsule consists of three D4d-CDMB-8 and two Cora subunits and contains a centrally bound I2 molecule as inferred from single-crystal and powder X-ray diffraction studies as well as solid-state 13C NMR and Raman spectroscopy. These analyses were complemented by solution-phase 1H NMR and UV-vis spectroscopic studies. No evidence of I2 escape from the capsule is seen, even at high temperatures (e.g., up to 418 K). The bound I2 is likewise protected from reaction with alkali or standard reductants in aqueous solution (e.g., saturated NaOH(aq) or aqueous Na2S2O3). It was also found that a mixed powder containing D4d-CDMB-8 and Cora in a 3:2 molar ratio could capture saturated I2 vapor or iodine from aqueous sources (e.g., 1.0 mM I2 in NaCl (35 wt %) or I2 + NaI(aq) (1.0 mM each)). The present system displays structural and functional features that go beyond what would be expected on the basis of a simple sum-of-the-components analysis. As such, it illustrates a new approach to creating self-assembled ensembles with emergent features.
A general strategy to optimize the performance of aza-BODIPY-based probes for enhanced photoacoustic properties
Yadav, Anuj K.,Tapia Hernandez, Rodrigo,Chan, Jefferson
, p. 415 - 441 (2021/07/26)
In this chapter, we describe a generalizable strategy to obtain a high PA output platform that is optimized for ratiometric imaging. Our approach entails conformationally restricting pendant aryl rings on the aza-BODIPY core to enhance orbital overlap which consequently increases the extinction coefficient. This strategy can potentially be applied to other dye platforms to enhance their signal intensity. We provide detailed protocols for the synthesis, in vitro characterization, and in vivo application.
Synthesis method of o-Dibromo compound
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Paragraph 0033-0040; 0068-0070, (2022/01/04)
The present invention discloses a synthesis method of o-dibromo compounds, said synthesis method comprising the following steps: preparation of olefins, brominated salts and a mixed solution of bromate; to the mixed solution of dropwise addition of hydrochloric acid solution for reaction; to the end of the reaction, the extraction of o-dibromo compounds in the reaction product; the synthesis method to inexpensive brominated salts (industrial or recycled brominated salts) and bromate as a bromine source, enhance the full use of applicable resources; after the end of the reaction after a simple filtration treatment to obtain a sufficient purity of the product, It can reduce production costs; at the same time, facilitate the transportation and storage of raw materials, and improve the working environment. The synthesis method of the present invention is simple and easy to operate, high safety, small pollution, simple post-treatment, low production cost, product yield and purity can meet the production needs, is both cost advantages and safety and environmental advantages of the industrializable process.
Green bromination method
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Paragraph 0059-0061, (2021/06/13)
The invention discloses a green bromination method, and belongs to the field of green organic chemistry. Under the conditions of room temperature, opening and neutrality, reaction raw materials are aromatic hydrocarbon, olefin, alkyne, tryptamine, tryptophane and derivatives thereof with different functional groups, a bromine source is MBrx (M is Fe , Fe , Ce and the like, and x is 2-3), and the unique oxidant is H2O2. Brominated alkanes, alkenes, aromatic hydrocarbons, pyrrolo-indolines and furo-indolines and derivatives thereof can be produced. The bromination reaction is carried out by using easily available and cheap reagents (such as FeBr2, CeB3 and H2O2) in the market and the solvent, and the method has the characteristics of mild reaction conditions, wide substrate application range, simple steps, easiness in operation and no need of separation, is a green, environment-friendly and safe bromination reaction method, and has a good application prospect.
Dibrominated addition and substitution of alkenes catalyzed by Mn2(CO)10
Chan, Albert S. C.,Jiang, Yi,Meng, Shanshui,Song, Xianheng,Zhang, Hong,Zou, Yong
supporting information, p. 13385 - 13388 (2021/12/17)
A practical method for the dibromination of alkenes without using molecular bromine is consistently appealing in organic synthesis. Herein, we report Mn-catalyzed dibrominated addition and substitution of alkenes only with N-bromosuccinimide, producing a variety of synthetically valuable dibrominated compounds in moderate to high yields. This journal is
Dihalogenation of Alkenes Using Combinations of N-Halosuccinimides and Alkali Metal Halides
Barrio, Pablo,García-Pedrero, Olaya,López-Matanza, Pablo,Rodríguez, Félix,Rubio-Presa, Rubén
supporting information, p. 4762 - 4766 (2021/09/10)
A simple, efficient and eco-friendly method for the vicinal dihalogenation of alkenes is described. The reaction is performed with a combination of a N-halosuccinimide and an alkali metal halide using environmentally benign solvents such as acetic acid an
