28022-44-8

Basic information

• Product Name: m-Bromostyrene 7,8-oxide
• Synonyms: m-Bromostyrene 7,8-oxide;(3-Bromophenyl)oxirane;m-Bromostyrene oxide;2-(3-Bromophenyl)oxirane;3-Bromostyrene oxide;1-Bromo-3-(epoxyethyl)benzene;Benzene, 1-bromo-3-(epoxyethyl)-;Brn 1306939
• CAS NO: 28022-44-8
• Molecular Formula: C₈H₇BrO
• Molecular Weight: 199.04
• Mol File: 28022-44-8.mol

Chemical Properties

• Boiling Point: 249 ºC
• Flash Point: 99 ºC
• Appearance: /
• Density: 1.596
• Vapor Pressure: 0.0363mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: m-Bromostyrene 7,8-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: m-Bromostyrene 7,8-oxide(28022-44-8)
• EPA Substance Registry System: m-Bromostyrene 7,8-oxide(28022-44-8)

Safety Data

• Hazardous Substances Data: 28022-44-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
m-Bromostyrene 7,8-oxide serves as a valuable intermediate in organic synthesis, particularly for the production of pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique combination of bromine and epoxide functionalities allows for a wide range of chemical reactions, making it a versatile component in the synthesis of various target molecules.
Used as a Building Block for Complex Molecules:
Due to its reactive nature, m-Bromostyrene 7,8-oxide is utilized as a building block for constructing more intricate molecular structures. Its presence in these structures can impart specific properties, such as increased reactivity or selectivity, which are essential for advanced applications in material science, pharmaceutical development, and other research areas.
Used in Research and Development:
m-Bromostyrene 7,8-oxide is also employed in research and development settings, where its properties are explored for potential applications in new chemical processes or as a means to understand the behavior of halogenated epoxides in various chemical systems.

InChI:InChI=1/C8H7BrO/c9-7-3-1-2-6(4-7)8-5-10-8/h1-4,8H,5H2

Upstream product

• 2039-86-3 3-bromostyrene 
• 18523-22-3 2,3'-dibromoacetophenone 
• 3132-99-8 m-bromobenzoic aldehyde 
• 2181-42-2 trimethylsulphonium iodide 
• 1774-47-6 trimethylsulfoxonium iodide 
• 6814-64-8 methylenedimethyl sulfurane 
• 64741-01-1 m-chloroperoxybenzoic acid 

Downstream Products

• 188974-19-8 N-ethyl-N-<2-(benzothien-3-yl)ethyl>-N-<2-hydroxy-2-(3-bromophenyl)ethyl>amine 
• 691894-14-1 (R)-(+)-(3-bromophenyl)oxirane 
• 131567-05-0 (S)-(+)-2-(3-bromophenyl)oxirane 
• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 943910-36-9 5-(3-bromophenyl)oxazolidin-2-one 
• 109347-40-2 2-(3-bromophenyl)acetaldehyde 
• 944801-48-3 2-bromo-6-(3-bromophenyl)naphthalene 

Relevant articles and documents

Kinetic resolution ofN-aryl β-amino alcoholsviaasymmetric aminations of anilines

An efficient kinetic resolution ofN-aryl β-amino alcohols has been developedviaasymmetricpara-aminations of anilines with azodicarboxylates enabled by chiral phosphoric acid catalysis. Broad substrate scope and high kinetic resolution performances were afforded with this method. Control experiments supported the critical roles of the NH and OH group in these reactions.

Epoxidation of Alkenes with Molecular Oxygen as the Oxidant in the Presence of Nano-Al 2O 3

The nano-Al 2O 3-promoted epoxidation of alkenes with molecular oxygen as the oxidant has been developed, providing an efficient route to a variety of epoxides in moderate to excellent yields. The environmentally friendly and efficient nano-Al 2O 3catalyst could be easily recovered and reused five times without significant loss of activity.

Reprogramming Epoxide Hydrolase to Improve Enantioconvergence in Hydrolysis of Styrene Oxide Scaffolds

Enantioconvergent hydrolysis by epoxide hydrolase is a promising method for the synthesis of important vicinal diols. However, the poor regioselectivity of the naturally occurring enzymes results in low enantioconvergence in the enzymatic hydrolysis of styrene oxides. Herein, modulated residue No. 263 was redesigned based on structural information and a smart variant library was constructed by site-directed modification using an “optimized amino acid alphabet” to improve the regioselectivity of epoxide hydrolase from Vigna radiata (VrEH2). The regioselectivity coefficient (r) of variant M263Q for the R-isomer of meta-substituted styrene oxides was improved 40–63-fold, and variant M263V also exhibited higher regioselectivity towards the R-isomer of para-substituted styrene oxides compared with the wild type, which resulted in improved enantioconvergence in hydrolysis of styrene oxide scaffolds. Structural insight showed the crucial role of residue No. 263 in modulating the substrate binding conformation by altering the binding surroundings. Furthermore, increased differences in the attacking distance between nucleophilic residue Asp101 and the two carbon atoms of the epoxide ring provided evidence for improved regioselectivity. Several high-value vicinal diols were readily synthesized (>88% yield, 90%–98% ee) by enantioconvergent hydrolysis using the reprogrammed variants. These findings provide a successful strategy for enhancing the enantioconvergence of native epoxide hydrolases through key single-site mutation and more powerful enzyme tools for the enantioconvergent hydrolysis of styrene oxide scaffolds into single (R)-enantiomers of chiral vicinal diols. (Figure presented.).

Integration of Enhanced Sampling Methods with Saturation Transfer Difference Experiments to Identify Protein Druggable Pockets

Saturation transfer difference (STD) is an NMR technique conventionally applied in drug discovery to identify ligand moieties relevant for binding to protein cavities. This is important to direct medicinal chemistry efforts in small-molecule optimization processes. However, STD does not provide any structural details about the ligand-target complex under investigation. Herein, we report the application of a new integrated approach, which combines enhanced sampling methods with STD experiments, for the characterization of ligand-target complexes that are instrumental for drug design purposes. As an example, we have studied the interaction between StOASS-A, a potential antibacterial target, and an inhibitor previously reported. This approach allowed us to consider the ligand-target complex from a dynamic point of view, revealing the presence of an accessory subpocket which can be exploited to design novel StOASS-A inhibitors. As a proof of concept, a small library of derivatives was designed and evaluated in vitro, displaying the expected activity.

Regio- and chemoselective rearrangement of terminal epoxides into methyl alkyl and aryl ketones

The development of the highly active pincer-type rhodium catalyst 2 for the nucleophilic Meinwald rearrangement of functionalised terminal epoxides into methyl ketones under mild conditions is presented. An excellent regio- and chemoselectivity is obtained for the first time for aryl oxiranes.

Green Organocatalytic Dihydroxylation of Alkenes

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Diastereoselective C?H Bond Amination for Disubstituted Pyrrolidines

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Indium(III) Chloride Promoted Highly Efficient Tandem Rearrangement-α-Addition Strategy towards the Synthesis of α-Hydroxyamides

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