5300-92-5

Usage

Uses

Used in Pharmaceutical Research:
5-(Bromomethyl)-3-(4-chlorophenyl)isoxazole is utilized as a drug candidate for the treatment of various diseases and disorders. Its unique structure and properties make it a promising candidate for the development of new therapeutic agents.
Used in Organic Synthesis:
The bromomethyl group in 5-(Bromomethyl)-3-(4-chlorophenyl)isoxazole makes it suitable for use in organic synthesis. It can serve as a building block for the production of other chemicals, contributing to the synthesis of a wide range of compounds.
Used in Agrochemicals:
The 4-chlorophenyl group present in 5-(Bromomethyl)-3-(4-chlorophenyl)isoxazole provides potential applications in the field of agrochemicals. It can be used to develop new pesticides or other agrochemical products, enhancing crop protection and yield.

InChI:InChI=1/C10H7BrClNO/c11-6-9-5-10(13-14-9)7-1-3-8(12)4-2-7/h1-5H,6H2

Upstream product

• 3717-23-5 (Z)-p-chlorobenzaldehyde oxime 
• 106-96-7 propargyl bromide 
• 104-88-1 4-chlorobenzaldehyde 
• 3848-36-0 4-chlorobenzaldoxime 
• 206055-90-5 3-(4-chlorophenyl)-5-hydroxymethylisoxazole 
• 28123-63-9 4-chlorobenzohydroximoyl chloride 

Downstream Products

• 5300-96-9 3-(4-chlorophenyl)-5-(iodomethyl)isoxazole 
• 1248699-32-2 3-fluoro-6-{[3-(4-chlorophenyl)isoxazol-5-yl]methyl}-2-(2-fluorophenyl)-6H-pyrrolo[2,3-c]pyridine 
• 1248699-23-1 6-{[3-(4-chlorophenyl)isoxazol-5-yl]methyl}-2-(2-fluorophenyl)-6H-pyrrolo[2,3-c]pyridine-3-carboxylic acid 
• 1248699-27-5 3-bromo-6-{[3-(4-chlorophenyl)isoxazol-5-yl]methyl}-2-(2-fluorophenyl)-6H-pyrrolo[2,3-c]pyridine 
• 1248699-28-6 3-chloro-6-{[3-(4-chlorophenyl)isoxazol-5-yl]methyl}-2-(2-fluorophenyl)-6H-pyrrolo[2,3-c]pyridine 
• 1248699-30-0 6-{[3-(4-chlorophenyl)isoxazol-5-yl]methyl}-2-(2-fluorophenyl)-6H-pyrrolo[2,3-c]pyridine-3-carbonitrile 
• 478048-78-1 C₁₈H₁₁ClN₂O₃ 
• 66046-42-2 (3-(4-chlorophenyl)isoxazol-5-yl)methanamine 
• 1245574-04-2 C₂₁H₂₄ClN₃O₄ 
• 754199-27-4 ethyl 1-((3-(4-chlorophenyl)isoxazol-5-yl)methyl)-1H-indole-2-carboxylate 

Relevant academic research and scientific papers

Product selectivity of thermal Buchner reaction of methyl 2-(3-arylisoxazol-5-yl)-2-diazoacetates with benzene, naphthalene and mesitylene, and ring-opening/closing reaction of products

Methyl 2-(3-arylisoxazol-5-yl)-2-diazoacetates were synthesized and the product selectivity of their thermal Buchner reaction with benzene, naphthalene and mesitylene was studied. The reaction of the isoxazolyl-substituted diazoacetates with benzene gave

Copper-catalysed synthesis of 3,5-disubstituted isoxazoles enabled by pyridinyl benzimidazol (PBI) as a bidentate N-chelating ligand under mild conditions

In this paper, we introduced pyridinyl benzimidazol (PBI) as an easy-to-handle and bidentate N-chelating ligand that promote clean synthesis of 3,5-disubstituted isoxazoles in the presence of copper acetate as catalyst. This catalytic approach initiates with the hydroxyamination of aldehydes followed by chlorination and then generation of nitrile oxide which subsequently undergoes click-type [3?+?2]-dipolar cycloaddition with alkynes to give isoxazoles. This method provides an alternative green process to construct isoxazole derivatives.

Synthesis of Halomethyl Isoxazoles/Cyclic Nitrones via Cascade Sequence: 1,2-Halogen Radical Shift as a Key Link

A novel iminoxyl radical-promoted dichotomous regioselective 5-exo-trig cyclization onto vinylic halogen/1,2-halogen radical shift sequence is developed for the synthesis of halomethyl isoxazoles/cyclic nitrones using β-halo-β,?- and ?-halo-?,?-unsaturated ketoximes as the substrates and PhI(OAc)2/TEMPO as the oxidation system. DFT calculations reveal that a halogen-bridged three-membered ring transition state is involved in the 1,2-Cl-/Br-atom shift, while the 1,2-I atom migration can be taken into account with an elimination/readdition mechanism. The migration ability was indicated to be ranked in the following order: I > Br > Cl.

Synthesis and in vitro biological evaluation of novel coumarin derivatives containing isoxazole moieties on melanin synthesis in B16 cells and inhibition on bacteria

A novel series of coumarin derivatives 6a–o, bearing isoxazole moieties were designed and synthesized. After that, they were evaluated for melanin synthesis in murine B16 cells and inhibitory effect on the growth of CA (Candida albicans), EC (Escherichia coli), SA (Staphylococcus aureus). It was found that eleven compounds (6b–f, 6j–o) showed a better activity on melanin synthesis than positive control (8-MOP). Among them, compounds 6d (242%) and 6f (390%), with nearly 1.6 and 2.6-fold potency compared with 8-MOP (149%) respectively, were recognized as the most promising candidate hits for further pharmacological study of anti-vitiligo. Seven halogen substituted compounds exhibited moderate antimicrobial activity against CA. It is interesting that 6e–f and 6l–m, which had two halogens on the benzene showed a comparable activity with Amphotericin B against CA. The evaluation of melanin synthesis in B16 cells and inhibitory effect on bacteria of above structurally diverse derivatives had also led to an outline of structure-activity relationship.

Synthesis and bioactivity of novel isoxazole chalcone derivatives on tyrosinase and melanin synthesis in murine B16 cells for the treatment of vitiligo

A new series of chalcone derivatives 1–18, bearing isoxazole moieties were designed and synthesized, and biologically evaluated for their activity on mushroom tyrosinase and melanin synthesis in murine B16 cells. The result indicated that most of prepared compounds 1–18 showed potent activating effect on tyrosinase, especially for 1–2, 4, 6–7, 9 and 15. Among them, compounds 2, 4 and 9 demonstrated the best activity with EC50?=?1.3, 2.5 and 3.0?μmol·L?1respectively, much better than the positive control 8-methoxypsoralan (8-MOP, EC50?=?14.8?μmol·L?1); In B16 cells, all the tested compounds exhibited a stronger activity on melanogenesis than 8-MOP (with the value of 115%). It was interesting that derivatives substituted with halogen (1, 2, 4, 5, 7, 9) were generally more potent. Compounds 2 (463%) and 18 (438%) with 3 and 4-fold potency compared with 8-MOP respectively, were recognized as the most promising candidate hits for further pharmacological study of anti-vitiligo.

PARTIALLY SATURATED NITROGEN-CONTAINING HETEROCYCLIC COMPOUND

There are provided compounds having a superior PHD2 inhibitory effect that are represented by general formula (I'): (in the above-mentioned general formula (I'), W, Y, R2, R3, R4, and Y4 are as described hereinabove), or pharmaceutically acceptable salts thereof.

Design, synthesis, and herbicidal activities of novel 2-cyanoacrylates containing isoxazole moieties

A series of novel 2-cyanoacrylates containing an isoxazole moiety were designed and synthesized. Their structures were characterized by 1H NMR and elemental analysis (or high-resolution mass spectrometry). Their herbicidal activities against four species were evaluated, and the results indicated that some of the title compounds showed excellent herbicidal activities against rape and amaranth pigweed in postemergence treatment even at a dose of 75 g/ha.

Fungicidal 3-phenyl-5-(substituted methyl) isoxaxoles

A class of isoxazoles having a phenyl or substituted-phenyl group at the 3-position and a substituted-methyl group at the 5-position are useful for the control of fungal foliar phytopathogens.