Welcome to LookChem.com Sign In|Join Free
  • or

Encyclopedia

Isoxazole

Base Information Edit
  • Chemical Name:Isoxazole
  • CAS No.:288-14-2
  • Molecular Formula:C3H3NO
  • Molecular Weight:69.0629
  • Hs Code.:29349990
  • European Community (EC) Number:206-018-7
  • NSC Number:137774
  • UNII:00SRW0M6PW
  • DSSTox Substance ID:DTXSID7059775
  • Nikkaji Number:J2.565H
  • Wikipedia:Isoxazole
  • Wikidata:Q899683
  • Metabolomics Workbench ID:55152
  • ChEMBL ID:CHEMBL13257
  • Mol file:288-14-2.mol
Isoxazole

Synonyms:Isoxazole;Isoxazoles

Suppliers and Price of Isoxazole
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Isoxazole
  • 100mg
  • $ 60.00
  • TCI Chemical
  • Isoxazole >95.0%(GC)
  • 5g
  • $ 24.00
  • Sigma-Aldrich
  • Isoxazole 99%
  • 25g
  • $ 98.30
  • Sigma-Aldrich
  • Isoxazole 99%
  • 5g
  • $ 26.90
  • Matrix Scientific
  • Isoxazole 98%
  • 100g
  • $ 108.00
  • Matrix Scientific
  • Isoxazole 98%
  • 5g
  • $ 10.00
  • Matrix Scientific
  • Isoxazole 98%
  • 25g
  • $ 29.00
  • Labseeker
  • Isoxazole 95
  • 100g
  • $ 470.00
  • Labseeker
  • Isoxazole 95
  • 50g
  • $ 383.00
  • Chemenu
  • Isoxazole 98%
  • 500g
  • $ 305.00
Total 114 raw suppliers
Chemical Property of Isoxazole Edit
Chemical Property:
  • Appearance/Colour:colorless liquid 
  • Vapor Pressure:51.7mmHg at 25°C 
  • Melting Point:-67.1°C 
  • Refractive Index:n20/D 1.427(lit.)  
  • Boiling Point:95.5 °C at 760 mmHg 
  • PKA:-2.0(at 25℃) 
  • Flash Point:8.9 °C 
  • PSA:26.03000 
  • Density:1.055 g/cm3 
  • LogP:0.67460 
  • Storage Temp.:Store at RT. 
  • Solubility.:167g/l 
  • XLogP3:0.1
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:2
  • Rotatable Bond Count:0
  • Exact Mass:69.021463719
  • Heavy Atom Count:5
  • Complexity:30.1
Purity/Quality:

99% *data from raw suppliers

Isoxazole *data from reagent suppliers

Safty Information:
  • Pictogram(s): FlammableF, IrritantXi 
  • Hazard Codes:F,Xi 
  • Statements: 11 
  • Safety Statements: 16-23/33-33-29-7/9 
MSDS Files:

SDS file from LookChem

Useful:
  • Chemical Classes:Nitrogen Compounds -> Other Nitrogen Compounds
  • Canonical SMILES:C1=CON=C1
  • General Description Isoxazole is a five-membered heterocyclic compound containing oxygen and nitrogen atoms, which serves as a key structural motif in various synthetic and medicinal chemistry applications. It can be synthesized through 1,3-dipolar cycloaddition reactions involving nitrile oxides and alkenes or alkynes, often under environmentally benign conditions using mediators like potassium chloride in water. Isoxazole derivatives are also accessible via oxidative methods, such as the conversion of aldoximes to nitrile oxides using hypervalent iodine reagents, followed by cycloaddition. Additionally, selective modulation of reaction conditions, such as base strength and catalyst presence, can favor isoxazole formation over competing pathways like Michael additions. Some isoxazole-containing hybrid molecules have been explored for biological activity, though not all exhibit significant antimicrobial effects.
Technology Process of Isoxazole

There total 53 articles about Isoxazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Guidance literature:
Guidance literature:
With hydroxylamine hydrochloride; at 110 - 120 ℃; Green chemistry;
DOI:10.2174/15701786113109990032
Guidance literature:
With hydroxylamine hydrochloride; In water; at 70 ℃; for 3.5h;
DOI:10.3762/bjoc.7.18
Refernces Edit

Synthesis of Aliphatic 1,3-Dinitro Compounds

10.1055/s-1996-4150

The study focuses on the synthesis of aliphatic 1,3-dinitro compounds, which can serve as precursors for various 1,3-difunctionalized compounds and heterocycles. The researchers developed a method to prepare these compounds by reacting primary aliphatic nitro compounds with primary or secondary α-nitroalkenes in the presence of catalytic amounts of triethylamine or potassium carbonate. The reactions were carried out at room temperature and yielded good results. The study also explored the reaction conditions and the yields and physical constants of the products. Additionally, the researchers investigated the instability of certain 2-aryl-1,3-dinitro compounds and the formation of by-products like isoxazolines and isoxazoles under specific conditions. The synthesized compounds were characterized using various spectroscopic techniques, and the structures of some compounds were confirmed through X-ray crystallography.

Oxidation of oximes to nitrile oxides with hypervalent iodine reagents

10.1021/ol900194v

The study explores an efficient method for converting aldoximes into nitrile oxides using iodobenzenediacetate (DIB) in methanol (MeOH) with a catalytic amount of trifluoroacetic acid (TFA). The nitrile oxides generated can be trapped in situ with olefins, leading to the formation of isoxazolines or isoxazoles, depending on the type of trap used. The study also investigates tandem oxidative processes, such as oxidative methoxylation or amidation of phenols, followed by intramolecular nitrile oxide cycloaddition (INOC), yielding synthetically valuable tricyclic intermediates. The findings demonstrate that DIB is an effective oxidant for aldoximes under these conditions, and the resulting intermediates hold potential for the synthesis of nitrogenous compounds.

An environmentally benign synthesis of isoxazolines and isoxazoles mediated by potassium chloride in water

10.1016/j.tetlet.2014.02.118

The study presents an environmentally benign method for synthesizing isoxazolines and isoxazoles via a cycloaddition reaction mediated by potassium chloride (KCl) in water. The key chemicals involved are aldoximes, which are oxidized to nitrile oxides by hypochlorous acid generated in situ from KCl and the oxidant Oxone?. These nitrile oxides then undergo a 1,3-dipolar cycloaddition with alkenes or alkynes to form the desired isoxazolines and isoxazoles. The process is optimized to achieve high yields and involves using KCl as a mediator, Oxone? as the oxidant, and water as the solvent, offering a green and efficient alternative to traditional methods.

Michael additions versus cycloaddition condensations with ethyl nitroacetate and electron-deficient olefins

10.1002/chem.200802652

The research study on the competitive reactions between ethyl nitroacetate and electron-deficient olefins under various reaction conditions and catalysts. The purpose of the study was to understand how these reactions could be modulated to favor either Michael additions or cycloaddition-condensations, leading to the formation of either Michael adducts or isoxazole derivatives, respectively. The researchers concluded that the reactions could be selectively steered towards one product or the other by adjusting the strength of the base and the presence of a copper(II) catalyst. Key chemicals used in the process included ethyl nitroacetate as the primary nitro compound, various electron-deficient olefins as dipolarophiles, and bases such as DABCO, DBU, and NMP, as well as copper(II) acetate as a catalyst. The study demonstrated that by manipulating the catalytic system, one could selectively form either Michael adducts or isoxazoline cycloadducts, marking the first report on such selective formation from primary nitro compounds through modulation of the catalytic system.

Synthesis and biological screening of 4-(3,3-dimethylspiro{bicyclo[2.2.1] heptan-2,5′-isoxazoline-2}- 3′-yl)-2-aryl-2,3-dihydro-1H-1,5- benzodiazepines

10.1002/jhet.194

The research involves the synthesis of a series of novel hybrid molecules that combine isoxazoles and benzodiazepines, with a dimethyl bicycloheptyl group added to enhance lipophilicity. The aim was to create compounds that could potentially act on multiple biological targets or enhance each other's activity. Key chemicals used in the synthesis include camphene, acetone, iron (III) nitrate nonahydrate, various aromatic aldehydes, and o-phenylenediamine. The synthesized compounds were characterized using techniques like NMR and IR spectroscopy. The compounds were then screened for their antibacterial and antifungal activities against a range of microbial strains, but none showed promising antimicrobial or antifungal activity up to concentrations of 180 μg/mL.

Post RFQ for Price