86256-88-4

Basic information

• Product Name: 3-Bromo-5-phenyl-4,5-dihydroisoxazole
• Synonyms: 3-Bromo-5-phenyl-4,5-dihydroisoxazole;3-bromo-4,5-dihydro-5-phenylIsoxazole
• CAS NO: 86256-88-4
• Molecular Formula: C₉H₈BrNO
• Molecular Weight: 226.06992
• Mol File: 86256-88-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 283.845°C at 760 mmHg
• Flash Point: 125.465°C
• Appearance: /
• Density: 1.569g/cm³
• Vapor Pressure: 0.005mmHg at 25°C
• Refractive Index: 1.625
• CAS DataBase Reference: 3-Bromo-5-phenyl-4,5-dihydroisoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-5-phenyl-4,5-dihydroisoxazole(86256-88-4)
• EPA Substance Registry System: 3-Bromo-5-phenyl-4,5-dihydroisoxazole(86256-88-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 86256-88-4(Hazardous Substances Data)

Usage

General Description

3-Bromo-5-phenyl-4,5-dihydroisoxazole is a chemical compound that belongs to the class of dihydroisoxazoles. It is a heterocyclic organic compound containing a bromine atom, a phenyl group, and an isoxazole ring. 3-Bromo-5-phenyl-4,5-dihydroisoxazole has potential applications in the pharmaceutical industry as it exhibits various biological activities, including antimicrobial, anti-inflammatory, and anticonvulsant properties. It can also be used as a building block in organic synthesis to create more complex molecules. The structure and properties of 3-Bromo-5-phenyl-4,5-dihydroisoxazole make it a valuable and versatile compound with potential for further research and development in various scientific and industrial fields.

InChI:InChI=1/C9H8BrNO/c10-9-6-8(12-11-9)7-4-2-1-3-5-7/h1-5,8H,6H2

Upstream product

• 100-42-5 styrene 
• 74213-24-4 N-dibromomethylidenehydroxylamine 
• 36617-02-4 1-bromo-2-phenylcyclopropane 
• 32523-76-5 cis-1-bromo-2-phenylcyclopropane 

Downstream Products

• 41856-54-6 3-methoxy-5-phenylisoxazoline 
• 140176-77-8 2-ethyl-5-phenylisoxazolidin-3-one 
• 53827-05-7 2-methyl-5-phenylisoxazolidin-3-one 
• 73627-97-1 3-hydroxy-3-phenylpropanenitrile 
• 7497-61-2 methyl 3-hydroxy-3-phenylpropionate 
• 1130365-41-1 5-phenyl-3-pyrrolidin-1-yl-4,5-dihydro-isoxazole 
• 1130365-43-3 1-(5-phenyl-4,5-dihydro-isoxazol-3-yl)-piperidine 
• 1130365-60-4 1-(5-phenyl-4,5-dihydro-isoxazol-3-yl)-4-methyl-piperidine 
• 1130365-46-6 1-(5-phenyl-4,5-dihydro-isoxazol-3-yl)-azepane 
• 1130365-40-0 diethyl-(5-phenyl-4,5-dihydro-isoxazol-3-yl)-amine 
• 1130365-35-3 butyl-(5-phenyl-4,5-dihydro-isoxazol-3-yl)-amine 
• 1130365-49-9 3-(5-phenyl-4,5-dihydro-isoxazol-3-ylamino)-propan-1-ol 
• 1130365-38-6 benzyl-(5-phenyl-4,5-dihydro-isoxazol-3-yl)-amine 
• 1161817-38-4 3-butoxy-5-phenyl-4,5-dihydro-isoxazole 

Relevant articles and documents

Effects of 3-Bromo-4,5-dihydroisoxazole Derivatives on Nrf2 Activation and Heme Oxygenase-1 Expression

Natural and synthetic electrophilic compounds have been shown to activate the antioxidant protective Nrf2 (nuclear factor erythroid 2-related factor 2)/heme oxygenase-1 (HO-1) axis in cells and tissues. Here, we tested the ability of different isoxazoline-based electrophiles to up-regulate Nrf2/HO-1. The potency of activation is dependent on the leaving group at the 3-position of the isoxazoline nucleus, and an additional ring on the molecule limits the Nrf2/HO-1 activating properties. Among the synthetized compounds, we identified 3-bromo-5-phenyl-4,5-dihydroisoxazole 1 as the derivative with best activating properties in THP-1 human monocytic cells. We have confirmed that the target of our compounds is the Cys151 of the BTB domain of Keap1 by using mass spectrometry analyses and X-ray crystallography. Our findings demonstrate that these compounds affect the Nrf2/HO-1 axis and highlight a positive activity that can be of relevance from a therapeutic perspective in inflammation and infection.

Discovery of covalent inhibitors of glyceraldehyde-3-phosphate dehydrogenase, a target for the treatment of malaria

We developed a new class of covalent inhibitors of Plasmodium falciparum glyceraldehyde-3-phosphate dehydrogenase, a validated target for the treatment of malaria, by screening a small library of 3-bromo-isoxazoline derivatives that inactivate the enzyme through a covalent, selective bond to the catalytic cysteine, as demonstrated by mass spectrometry. Substituents on the isoxazolinic ring modulated the potency up to 20-fold, predominantly due to an electrostatic effect, as assessed by computational analysis.

Δ2-isoxazolines from arylcyclopropanes: III. Phenylcyclopropanes substituted in three-membered ring in reaction with nitrosyl chloride activated with oxides of sulfur(IV, VI)

The reaction of phenylcyclopropanes substituted in the three-membered ring with nitrosyl chloride activated with sulfur(IV, VI) oxides provided in good yield substituted 5-phenylisoxazolines as a mixture of structural isomers.