300-87-8

Basic information

• Product Name: 3,5-Dimethylisoxazole
• Synonyms: DIMETHYLISOXAZOLE(3,5-);AKOS BBS-00006705;3,5-DISO;3,5-DIMETHYLISOXAZOLE;3,5-DIMETHYLISOOXAZOLE;3,5-DIMETHOXYISOXAZOLE;3,5-dimethyl-isoxazol;3,5-Dwumetyloizoksazolu
• CAS NO: 300-87-8
• Molecular Formula: C₅H₇NO
• Molecular Weight: 97.12
• EINECS: 206-100-2
• Product Categories: Oxazole&Isoxazole;API intermediates;Building Blocks;Heterocyclic Building Blocks;Isoxazoles;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 300-87-8.mol
• Article Data: 22

Chemical Properties

• Melting Point: -14℃
• Boiling Point: 142-144 °C(lit.)
• Flash Point: 88 °F
• Appearance: clear colourless to pale yellow liquid
• Density: 0.99 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.51mmHg at 25°C
• Refractive Index: n20/D 1.442(lit.)
• Storage Temp.: Flammables area
• Solubility: 50.9g/l
• PKA: -1.35±0.28(Predicted)
• Water Solubility: insoluble
• BRN: 106324
• CAS DataBase Reference: 3,5-Dimethylisoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dimethylisoxazole(300-87-8)
• EPA Substance Registry System: 3,5-Dimethylisoxazole(300-87-8)

Safety Data

• Hazard Codes: Xn
• Statements: 10-20/21/22
• Safety Statements: 16-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: NY2774200
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 300-87-8(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to pale yellow liquid

Uses

The optimization of 3,5-dimethylisoxazole derivatives to develop potent inhibitors of the BET (bromodomain and extra terminal domain) bromodomain family with good ligand efficiency. It has hypoglycemic activity.

Application

3,5-dimethylisoxazole is an organic intermediate used in the preparation of 4-(chloromethyl)-3,5-dimethylisoxazole.

Preparation

3,5-Dimethylisozole can be synthesized from acetylacetone and hydroxylamine hydrochloride in one step off ring.

InChI:InChI=1/C5H7NO/c1-4-3-5(2)7-6-4/h3H,1-2H3

Upstream product

• 832114-00-8 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole 
• 16114-47-9 3,5-dimethylisoxazole-4-boronic acid 
• 21139-18-4 4,6-dimethyl-1-phenyl-2-oxopyrimidine 
• 71989-66-7 4-bromo-3,5-dimethyl-1-hydroxypyrazole 2-oxide 
• 13545-14-7 1-benzyloxy-4,6-dimethyl-2(1H)-pyrimidinone 
• 55393-93-6 2-acetyl-3-methyl-2H-azirine 
• 10557-85-4 4-iodo-3,5-dimethylisoxazole 
• 53009-14-6 3,5-dimethyl-5-hydroxy-Δ²-isoxazoline 
• 123-54-6 acetylacetone 
• 2157-56-4 pentane-2,4-dione dioxime 
• 1118-66-7 4-amino-3-penten-2-one 
• 71989-58-7 3,5-Dimethyl-2-oxy-pyrazol-1-ol 
• 60-29-7 diethyl ether 
• 10026-13-8 phosphorus pentachloride 

Downstream Products

• 157984-60-6 1-(4-fluoro-phenyl)-2-(3-methyl-isoxazol-5-yl)-ethanone 
• 873876-95-0 (R)-6-((R)-2-Hydroxy-propyl)-4-phenylsulfanyl-tetrahydro-pyran-2-one 
• 873876-96-1 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (R)-1-methyl-2-((R)-6-oxo-4-phenylsulfanyl-tetrahydro-pyran-2-yl)-ethyl ester 
• 71939-67-8 (R)-1-methyl-2-[(S)-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl 3-(3,4-dihydroxyphenyl)propanoate 
• 131613-66-6 (-)-<5(S),7(R)>-7-<5-(oct-2-enolide)-3',4'-bis-(t-butyldimethylsilyloxy)>-dihydrocinnamate 
• 84654-08-0 5-Methanesulfinylmethyl-3-methyl-isoxazole 
• 91945-18-5 4-[5-(3-Methyl-isoxazol-5-yl)-pentyloxy]-benzoic acid 
• 91945-32-3 1-(4-{[7-(3-methyl-5-isoxazolyl)heptyl]oxy}phenyl)ethanone 
• 91945-20-9 3-[7-(3-Methyl-isoxazol-5-yl)-heptyloxy]-benzoic acid 
• 91945-21-0 4-[8-(3-Methyl-isoxazol-5-yl)-octyloxy]-benzoic acid 
• 91945-23-2 5-[7-(4-ethoxycarbonylphenoxy)heptyl]-3-methylisoxazole 
• 91945-35-6 3-methyl-5-[7-(4-carboxamidophenoxy)heptyl]isoxazole 
• 91945-17-4 4-<<7-(3-methyl-5-isoxazolyl)heptyl>oxy>benzoic acid 
• 61449-06-7 4-(3-methyl-isoxazol-5-yl)-1,3-diphenyl-butan-1-one 

Relevant articles and documents

Styrylisoxazole-based fluorescent probes for the detection of hydrogen sulfide

Styrylisoxazoles bearing a nitro group linked to bulky aromatic rings have been synthesized and examined for their absorption and emission studies in organic solvents and water. The molecules showed emission in the visible region with significant solvatochromic emission shifts influenced by the extended conjugation of aromatic rings and intramolecular charge transfer. These absorption and emission changes were used for the efficient and sensitive detection of trace concentrations of hydrogen sulfide (H2S) through the reduction of the nitro group to the amine group in the presence of aqueous sodium sulfide. The experimental results indicated that the probes exhibit an excellent emission response with large shifts in the emission and sensitivity with a micromolar detection limit.

Development of Gold-catalyzed [4+1] and [2+2+1]/[4+2] Annulations between Propiolate Derivatives and Isoxazoles

Two new gold-catalyzed annulations of isoxazoles with propiolates have been developed. Most isoxazoles follow an initial O attack on the alkyne to afford a [4+1] annulation product. This process results in a remarkable alkyne cleavage of initial propiolates. Unsubstituted isoxazoles proceed through an N attack step to yield formal [2+2+1]/[4+2] annulation products. These two annulation products arise initially from two seven-membered heterocyclic intermediates, which then lead to products.

Development and Scale-up of an Organocatalytic Enantioselective Process to Manufacture (S)-Pregabalin

Herein is reported the development of a new process to manufacture (S)-pregabalin. The method comprises six steps, run under the catalysis of a recyclable polymer bound phase transfer catalyst, and afforded (S)-pregabalin in overall 54% yield, starting from building blocks acetylacetone, isovaleraldehyde, and nitromethane.