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

Description

3,5-Dimethylisoxazole is a clear colorless to pale yellow liquid that serves as an organic intermediate in the synthesis of various compounds. It is known for its potential as a potent inhibitor of the BET bromodomain family and its hypoglycemic activity.

Uses

Used in Pharmaceutical Industry:
3,5-Dimethylisoxazole is used as a chemical intermediate for the development of potent inhibitors of the BET (bromodomain and extra terminal domain) bromodomain family. These inhibitors have potential applications in the treatment of various diseases by modulating the bromodomain family's interaction with acetylated histones and other proteins.
Used in Organic Synthesis:
3,5-Dimethylisoxazole is used as an organic intermediate in the preparation of 4-(chloromethyl)-3,5-dimethylisoxazole, which can be further utilized in the synthesis of various pharmaceuticals and other organic compounds.
Used in Medicinal Chemistry:
3,5-Dimethylisoxazole is used as a starting material for the design and synthesis of novel hypoglycemic agents. Its hypoglycemic activity makes it a promising candidate for the development of new drugs to treat diabetes and related metabolic disorders.

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

• 10557-85-4 4-iodo-3,5-dimethylisoxazole 
• 1118-66-7 4-amino-3-penten-2-one 
• 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 
• 123-54-6 acetylacetone 
• 71989-58-7 3,5-Dimethyl-2-oxy-pyrazol-1-ol 
• 59487-11-5 (3Z)-4-(isopropylamino)pent-3-en-2-one 
• 21139-18-4 4,6-dimethyl-1-phenyl-2-oxopyrimidine 
• 74360-11-5 1-(4-Methoxyphenyl)-4,6-dimethyl-2(1h)-pyrimidinone 
• 74152-12-8 4,6-Dimethyl-1-p-tolyl-1H-pyrimidin-2-one 
• 133329-05-2 3,5-Dimethyl-4,5-dihydro-isoxazol-5-ylamine 
• 2157-56-4 pentane-2,4-dione dioxime 
• 60-29-7 diethyl ether 
• 10026-13-8 phosphorus pentachloride 

Downstream Products

• 61449-10-3 3-Phenyl-4-(3-methyl-5-isoxazolyl)-butanal 
• 61449-09-0 1-(3-methyl-isoxazol-5-yl)-4-phenyl-but-3-en-2-ol 
• 27349-53-7 2-(3-methyl-isoxazol-5-yl)-1,1-diphenyl-ethanol 
• 19668-85-0 2-(3-methylisoxazol-5-yl)acetic acid 
• 61449-14-7 4-(3-methyl-isoxazol-5-yl)-3-phenyl-butyric acid 
• 51100-99-3 1,4-bis-(3-methyl-isoxazol-5-yl)-N,N'-di-p-tolyl-butane-2,3-diamine 
• 60729-68-2 1-(2-hydroxy-4-methoxy-6-methyl-phenyl)-2-(3-methyl-isoxazol-5-yl)-ethanone 
• 61449-04-5 1-(3-methyl-isoxazol-5-ylmethyl)-cyclohexanol 
• 61449-00-1 (+/-)-5-(2-hydroxy-2-p-tolylethyl)-3-methylisoxazole 
• 61449-18-1 5-(2-benzyloxy-2-phenyl-ethyl)-3-methyl-isoxazole 
• 41027-45-6 5-(1-benzyl-2-phenyl-ethyl)-3-methyl-isoxazole 
• 61449-13-6 4-(3-methyl-isoxazol-5-yl)-3-phenyl-butyric acid methyl ester 
• 51100-96-0 N-[2-(3-methyl-isoxazol-5-yl)-1-phenyl-ethyl]-aniline 
• 51101-01-0 3-methyl-5-styryl-isoxazole 

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.