36958-61-9

Usage

Uses

Used in Pharmaceutical Industry:
5-(BROMOMETHYL)-3-METHYLISOXAZOLE is used as a synthetic intermediate for the development of various pharmaceuticals. Its reactivity allows for the creation of new compounds with potential therapeutic properties, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 5-(BROMOMETHYL)-3-METHYLISOXAZOLE serves as a key intermediate in the synthesis of agrochemicals. Its ability to form new compounds makes it instrumental in developing products for crop protection and other agricultural applications.
Used in Organic Synthesis Research:
5-(BROMOMETHYL)-3-METHYLISOXAZOLE is utilized as a research compound in organic synthesis. Its unique structure and reactivity make it a subject of interest for scientists exploring new methods and reactions in organic chemistry, potentially leading to the discovery of novel organic compounds with various applications.

InChI:InChI=1/C5H6BrNO/c1-4-2-5(3-6)8-7-4/h2H,3H2,1H3

Upstream product

• 300-87-8 3,5-dimethyl-1,2-oxazole 
• 14716-89-3 3-methyl-5-isoxazolemethanol 
• 107-29-9 Acetaldehyde oxime 
• 106-96-7 propargyl bromide 
• 63366-79-0 3-methylisoxazole-5-carboxylic acid ethyl ester 
• 615-79-2 ethyl 2,4-diketopentanoate 

Downstream Products

• 102670-57-5 4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(3-methylisoxazol-5-yl)methoxybenzamide 
• 173850-34-5 3-methyl-5-(N-propargylaminomethyl) isoxazole 
• 185690-33-9 5-methyl-3-<(N-phenylamino)methyl>isoxazole 
• 61858-76-2 (3-methyl-isoxazol-5-ylmethyl)-triphenyl-phosphonium; bromide 
• 53257-36-6 4-bromo-5-bromomethyl-3-methyl-isoxazole 
• 392312-40-2 3-methyl-5-diethylaminomethylisoxazole 
• 341015-60-9 2-(3-methyl-isoxazol-5-yl)-2-methylsulfanyl-1-phenyl-ethanol 

Relevant academic research and scientific papers

Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

A convergent, nine-step (LLS), enantioselective synthesis of α-cyclopiazonic acid and related natural products is reported. The route features a) an enantioselective aziridination of an imine with a chiral sulfur ylide; b) a bioinspired (3+2)-cycloaddition of the aziridine onto an alkene; and c) installation of the acetyltetramic acid by an unprecedented tandem carbonylative lactamization/N?O cleavage of a bromoisoxazole.

Isoxazole-Derived Amino Acids are Bromodomain-Binding Acetyl-Lysine Mimics: Incorporation into Histone H4 Peptides and Histone H3

A range of isoxazole-containing amino acids was synthesized that displaced acetyl-lysine-containing peptides from the BAZ2A, BRD4(1), and BRD9 bromodomains. Three of these amino acids were incorporated into a histone H4-mimicking peptide and their affinity for BRD4(1) was assessed. Affinities of the isoxazole-containing peptides are comparable to those of a hyperacetylated histone H4-mimicking cognate peptide, and demonstrated a dependence on the position at which the unnatural residue was incorporated. An isoxazole-based alkylating agent was developed to selectively alkylate cysteine residues in situ. Selective monoalkylation of a histone H4-mimicking peptide, containing a lysine to cysteine residue substitution (K12C), resulted in acetyl-lysine mimic incorporation, with high affinity for the BRD4 bromodomain. The same technology was used to alkylate a K18C mutant of histone H3.

N-ACRYLIMINO HETEROCYCLIC COMPOUNDS

The present invention relates to N-acrylimino compound of formula (I): wherein X is O or S, in particular O; Het is a 5-or 6-membered carbon-bound or nitrogen-bound heterocyclic ring, W1-W2-W3-W4 represents a carbon chain group connected to N and C=N, and thus forming a saturated, unsaturated, or partially unsaturated 5 or 6 membered nitrogen containing heterocycle, wherein W1, W2, W3 and W4 each individually represent CRvRw, R1, R 2 may be hydrogen, halogen, etc. R3 is selected from the group consisting of hydrogen, halogen, CN, C1-C6-alkyl, etc. R4 is selected from the group consisting of hydrogen, halogen, CN, C1-C10-alkyl, etc. R5 is selected from the group consisting of hydrogen CN, C1-C10-alkyl, C2-C10-alkenyl C3-C8-cycloalkyl, S(O)nNR9aR9b, O-NR9aR9b, NR9aR9b, NR9a NR9aR9b, NR9aC(=O)R7a, NR9aC(=S)R7a, NR9aC(=O)NR9aR9b, NR9aC(=S)NR9aR9b, C(=O)OR8, C(=O)NR9aR9b, C(=S)NR9aR9b, C(=O)R7a, C(=S)R7a, a moitey Q-phenyl, where the phenyl ring is optionally substituted with 1, 2, 3, 4 or 5 identical or different substituents R10, and a moiety Q-HetNo. where HetNo. represents a 3- to 10- membered saturated, partly saturated or unsaturated aromatic heterocyclic ring. The invention also relates to the use of the N-acrylimino heterocyclic compounds, their stereoisomers, their tautomers and their salts,for combating invertebrate pests. Furthermore the invention relates also to methods of combating invertebrate pests, which comprises applying such compounds.

Synthesis of 5-bromomethylisoxazoles and their reactions with secondary amines

Treating R-3-chloro-4-bromo-2-buten-1-ones with hydroxylamine hydrochloride afforded 3-alkyl(aryl, furyl)-5-bromomethylisoxazoles. By reaction of the latter with secondary amines new previously unknown aminoisoxazoles were synthesized. 2005 Pleiades Publi

Synthesis and evaluation of 2β-oxyimino and alkenylpenicillanic acid sulfone derivatives as β-lactamase inhibitors

The synthesis and in vitro synergies of 2β-alkenyl and oxyiminopenam sulfone derivatives are described. Most of the compounds synthesized exhibited good inhibitory activities and synergistic antibacterial activities with piperacillin and ceftriaxone, resp

Regioisomeric 3-, 4- and 5-aminomethyl isoxazoles: Synthesis and muscarinic activity

A series of 3-, 4- and 5-aminomethyl isoxazoles and isoxazoles with one or two additional methyl groups at the heterocycle were synthesized in order to investigate the structural requirements, ie heterocyclic moiety, regiochemistry and length of an aminoalkyl unit, for muscarinic activity. This was assayed on isolated rabbit vas deferens (M1 receptor subtype) and isolated guinea-pig atrium (M2 receptor subtype) and ileum (M3 receptor subtype). The isoxazoles tested are one to three orders of magnitude less active than furane or oxadiazole derivatives, having similar structural characteristics except for the heterocycle. Thus, the differences in molecular point charges and charge distribution contribute to the muscarinic activity of these compounds more than small differences in molecular shape and conformational energies.