31709-50-9

Usage

General Description

3-(4-Bromophenyl)-5(4H)-isoxazolone is a chemical compound with the molecular formula C9H6BrNO2. It is a derivative of isoxazolone, a heterocyclic compound containing both oxygen and nitrogen atoms in the five-membered ring structure. The presence of the bromophenyl group in the molecule makes it useful in organic synthesis and as a building block for creating other chemical compounds. 3-(4-BROMOPHENYL)-5(4H)-ISOXAZOLONE may have potential applications in the pharmaceutical and agrochemical industries due to its unique structural properties. The presence of the bromine atom in the molecule also contributes to its chemical reactivity and potential for forming various derivatives for different purposes.

Upstream product

• 5868-56-4 [3-(4-bromo-phenyl)-isoxazol-5-yl]-boronic acid 
• 124-38-9 carbon dioxide 
• 59862-55-4 p-bromoacetophenone oxime 
• 42811-75-6 p-bromobenzonitrile N-oxide 
• 99-90-1 para-bromoacetophenone 
• 616-38-6 carbonic acid dimethyl ester 
• 126629-81-0 methyl 3-(4-bromophenyl)-3-oxopropanoate 
• 26510-95-2 ethyl 4-Bromobenzoylacetate 

Downstream Products

• 1416133-07-7 3-(4-bromophenyl)-4-fluoro-4-(2-nitro-1-phenylethyl)isoxazol-5(4H)-one 
• 192432-78-3 3-(4-bromophenyl)-5-chloroisoxazole 
• 67900-59-8 3-(4-bromophenyl)-5-methoxyisoxazole 

Relevant academic research and scientific papers

Construction of isoxazolone-fused phenanthridinesviaRh-catalyzed cascade C-H activation/cyclization of 3-arylisoxazolones with cyclic 2-diazo-1,3-diketones

A Rh(iii)-catalyzed cascade C-H activation/intramolecular cyclization of 3-aryl-5-isoxazolones with cyclic 2-diazo-1,3-diketones was described, leading to the formation of isoxazolo[2,3-f]phenanthridine skeletons. The protocol features the simultaneous one-pot formation of two new C-C/C-N bonds and one heterocycle in moderate-to-good yields with good functional group compatibility. It is amenable to large-scale synthesis and further transformation.

Palladium catalyzed insertion reaction of isocyanides with 3-arylisoxazol-5(4 H)-ones: Synthesis of 4-aminomethylidene isoxazolone derivates

A palladium catalyzed insert reaction of isocyanides to 3-arylisoxazol-5(4H)-ones for the construction of 4-aminomethylidene isoxazolone derivates is reported. In this transformation, only the C-H bond of the methylene group was involved while the remaining ring structure was retained. In general, this work provided a new protocol for the synthesis of 4-aminomethylidene isoxazolones.

Atom-Economic Silver-Catalyzed Difunctionalization of the Isocyano Group with Cyclic Oximes: Towards Pyrimidinediones

An unprecedented silver-catalyzed difunctionalization of the isocyano group with cyclic oximes is described. This method allows efficient and atom-economic assembly of a vast array of structurally novel and interesting pyrimidinediones, and tolerates a range of functionalities. The resulting products can be easily converted into some useful compounds. Furthermore, the method can also be applied for the late-stage modification of a few biologically active molecules.

Cooperative Catalysis with Coupled Chiral Induction in 1,3-Dipolar Cycloadditions of Azomethine Ylides

1,3-Dipolar cycloadditions (1,3-DC) between imino esters (as precursors of N-metallated azomethine ylides) and π-deficient alkenes are promoted by cooperative asymmetric Lewis acid/Br?nsted base catalysis. The components of these catalytic pairs are silver salts derived from enantiopure commercially available BINOL-based phosphoric acids and Cinchona alkaloids. Chiral phosphoric silver(I) salts promote HOMO raising of in situ formed 1,3-dipoles, whereas protonated cinchona alkaloids generate a LUMO lowering for the dipolarophiles resulting in a global acceleration of the 1,3-DC. The best results were obtained with BINOL-derived silver phosphate and hydrocinchonine. Matching between both cooperative metallo- and organocatalyst results in an enhanced enantiomeric excess, superior to that reached by both separate components. NOESY experiments and DFT calculations are compatible with a non-covalent interaction (hydrogen bond) between both catalysts, which results in close contacts and mutually coupled chiral environments.

An Aminocatalyzed Stereoselective Strategy for the Formal α-Propargylation of Ketones

A two-step reaction sequence is described for the asymmetric formal α-propargylation of ketones. This approach takes advantage of an aminocatalyzed conjugate addition of ketones to alkylidene isoxazol-5-ones, followed by a controlled nitrosative degradation event. The target compounds can be accessed in broad scope, in moderate to good yields, perfect diastereocontrol and good to excellent enantioselectivity.

Stereoselective Michael Halogenation Initiated Ring Closure (MHIRC) Synthesis of Spirocyclopropanes from Benzylidenemalononitriles and 3-Arylisoxazol-5(4H)-ones

The new chemical cascade reaction was found: the direct formation of substituted 4-oxo-2,7-diaryl-5-oxa-6-azaspiro[2.4]hept-6-ene-1,1-dicarbonitriles from benzylidenemalononitriles and 3-aryl-2-isoxazol-5(4H)-ones. The action of bromine on the equimolar mixture of benzylidenemalononitrile and 3-aryl-2-isoxazol-5(4H)-one in the basic alcohol solution results in stereoselective formation of spirobicycle containing the 2-isoxazolin-5-one and the cyclopropane fragments in 53-92% yields. Thus, the new simple and efficient ‘one-pot’ approach to substituted (2R*,3R*)-4-oxo-2,7-diaryl-5-oxa-6-azaspiro[2.4]hept-6-ene-1,1-dicarbonitriles was found directly from simple and reasonable starting compounds as benzylidenemalonitriles and 3-aryl-2-isoxazol-5(4H)-ones.