Isoxazole

Base Information

• 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

Synonyms:Isoxazole;Isoxazoles

Chemical Property of Isoxazole

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): F, Xi
• 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
• Description: As an important class of heterocycles, isoxazole is a five membered heterocyclic compound with various pharmacological actions, which is found in some natural products, such as ibotenic acid. It is used in the formation of the basis for a number of drugs, such as the COX-2 inhibitor valdecoxib and anti-inflammatory drugs. Isoxazoles are largely applied in the area of pharmaceuticals and therapeutics, including insecticidal, antibacterial, antibiotic, antitumour, antifungal, antituberculosis, anticancer and ulcerogenic. Besides, it has a great effect on reducing blood glucose, eliminating pain, resisting inflammation, killing harmful bacteria, controlling and reducing the risk of HIV. The isoxazole ring is an essential pharmacophore in modern drug discovery. Some beta-lactamase-resistant antibiotics contain an isoxazole group, including cloxacillin, dicloxacillin, flucloxacillin, and the isoxazole group is also found in some steroid drug such as danazol.
• Uses: Natural insecticide.

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%

→ ISOXAZOLE (288-14-2)

Guidance literature:

Reference yield: 85.5%

di(1,3-dioxolan-2-yl)methane (4405-17-8) → ISOXAZOLE (288-14-2)

Guidance literature:

With hydroxylamine hydrochloride; at 110 - 120 ℃; Green chemistry;

DOI:10.2174/15701786113109990032

Reference yield: 43.0%

malondialdehyde bis(diethyl acetal) (122-31-6) → ISOXAZOLE (288-14-2)

Guidance literature:

With hydroxylamine hydrochloride; In water; at 70 ℃; for 3.5h;

DOI:10.3762/bjoc.7.18

upstream raw materials:

Propargylic aldehyde

1,3,3-triethoxypropene

vinyl acetate

sodium cyanate

Downstream raw materials:

4-chloromethyl-isoxazole

3-ethoxyacrylonitrile

3,3-bis(ethyloxy)propanenitrile

4-bromo-1,2-oxazole

Refernces

• 1、 Nitlikar, Lakshmikant H.,Shinde, Devanand B.. "Development of safe and economical synthesis of isoxazole". . p. 637 - 639. Retrieved 2013/12/04.
• 2、 Pitteri, Bruno,Bortoluzzi, Marco. "Reactivity of neutral nitrogen donors in square-planar d8 metal complexes: The system chloro(2,2′:6′,2″-terpyridine)platinum(II) cation with five-membered N-donor heterocycles in methanol". . p. 2698 - 2704. Retrieved 2008/10/09.