Isoxazole, 3-phenyl-5-(2-thienyl)-

Base Information

• Chemical Name: Isoxazole, 3-phenyl-5-(2-thienyl)-
• CAS No.: 62218-62-6
• Molecular Formula: C13H9NOS
• Molecular Weight: 227.287
• DSSTox Substance ID: DTXSID50486976
• Nikkaji Number: J3.273.689K
• Wikidata: Q82328787
• Mol file: 62218-62-6.mol

Synonyms:62218-62-6;3-phenyl-5-(thiophen-2-yl)isoxazole;Isoxazole, 3-phenyl-5-(2-thienyl)-;3-phenyl-5-(2-thienyl)isoxazole;DTXSID50486976;3-phenyl-5-thiophen-2-yl-isoxazole

Chemical Property of Isoxazole, 3-phenyl-5-(2-thienyl)-

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 227.04048508
• Heavy Atom Count: 16
• Complexity: 230

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NOC(=C2)C3=CC=CS3

Technology Process of Isoxazole, 3-phenyl-5-(2-thienyl)-

There total 13 articles about Isoxazole, 3-phenyl-5-(2-thienyl)- 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: 82.0%

→ 3-phenyl-5-(2′-thienyl)isoxazole (62218-62-6)

Guidance literature:

at 20 ℃; Alkaline conditions;

Reference yield: 76.0%

2-Iodothiophene (3437-95-4,149762-92-5) + chromium(0) hexacarbonyl (199620-14-9,13007-92-6) + phenylacetylene (536-74-3) → 3-phenyl-5-(2′-thienyl)isoxazole (62218-62-6)

Guidance literature:

With hydroxylamine hydrochloride; potassium acetate; palladium dichloride; In N,N-dimethyl-formamide; at 70 ℃; for 18h; under 760.051 Torr;

DOI:10.1016/j.tetlet.2015.11.053

Reference yield: 56.0%

2-ethynyl-thiophene (4298-52-6) + N-hydroxy-1-phenylmethanesulfonamide → 3-phenyl-5-(2′-thienyl)isoxazole (62218-62-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); iodine; tetrabutylammonium periodite; In dichloromethane; at 20 ℃; for 10h; Irradiation; Inert atmosphere;

DOI:10.1055/s-0037-1609480

upstream raw materials:

2-bromo-1-phenyl-3-(thiophen-2-yl)prop-2-en-1-one

3-hydroxyamino-1-phenyl-3-thiophen-2-yl-propan-1-one oxime

2,3-dibromo-1-phenyl-3-thiophen-2-yl-propan-1-one

1-phenyl-3-(thiophen-2-yl)propane-1,3-dione

Refernces

• 1、 Noguchi, Teppei,Nishii, Yuji,Miura, Masahiro. "Rhodium-Catalyzed Cascade Annulative Coupling of 3,5-Diarylisoxazoles with Alkynes". . p. 258 - 270. Retrieved 2019/01/04.
• 2、 G?rgen, Christina,Müller, Thomas J. J.. "Facile consecutive three-component synthesis of 3,5-disubstituted isoxazoles". . p. 422 - 429. Retrieved 2017/07/05.