3-(3-Nitrophenyl)-5-chloroisoxazole

Base Information

• Chemical Name: 3-(3-Nitrophenyl)-5-chloroisoxazole
• CAS No.: 181057-91-0
• Molecular Formula: C9H5ClN2O3
• Molecular Weight: 224.603
• DSSTox Substance ID: DTXSID40452185
• Nikkaji Number: J880.768J
• Wikidata: Q82272636
• Mol file: 181057-91-0.mol

Synonyms:5-chloro-3-(3-nitrophenyl)-1,2-oxazole;3-(3-Nitrophenyl)-5-chloroisoxazole;181057-91-0;5-CHLORO-3-(3-NITROPHENYL)ISOXAZOLE;AGN-PC-0NEK30;SCHEMBL22348262;DTXSID40452185

Chemical Property of 3-(3-Nitrophenyl)-5-chloroisoxazole

Chemical Property:

• PSA: 71.85000
• LogP: 3.42640
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 223.9988697
• Heavy Atom Count: 15
• Complexity: 246

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)[N+](=O)[O-])C2=NOC(=C2)Cl

Technology Process of 3-(3-Nitrophenyl)-5-chloroisoxazole

There total 5 articles about 3-(3-Nitrophenyl)-5-chloroisoxazole 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: 87.0%

2-(3-nitrophenyl)-1,1-dichlorocyclopropane (145490-91-1) → 3-(3-nitrophenyl)-5-chloroisoxazole (181057-91-0)

Guidance literature:

With nitrosyl chloride sulfur trioxide; In dichloromethane; at 20 ℃; for 24h; chemospecific reaction;

DOI:10.1134/S1070428013020024

Reference yield: 15.0%

3-(3-nitrophenyl)isoxazol-5(4H)-one (103029-79-4) → 3-(3-nitrophenyl)-5-chloroisoxazole (181057-91-0)

Guidance literature:

With tetraethylammonium chloride; trichlorophosphate; In dichloromethane; at 120 ℃; for 2h; Reflux;

Reference yield: 8.0%

2-(3-nitrophenyl)-1,1-dichlorocyclopropane (145490-91-1) → m-Nitrocinnamic Acid (555-68-0,1772-76-5) + 3-nitro-benzaldehyde (99-61-6) + 3-(3-nitrophenyl)-5-chloroisoxazole (181057-91-0)

Guidance literature:

With sulfuric acid; nitric acid; at 0 ℃; for 1h;

upstream raw materials:

2-(3-nitrophenyl)-1,1-dichlorocyclopropane

3-(3-nitrophenyl)isoxazol-5(4H)-one

ethyl 3-oxo-3-(3-nitrophenyl)propanoate

3-(3-nitrophenyl)-3-oxopropionic acid methyl ester

Refernces

• 1、 -. "SUBSTITUTED BICYCLIC COMPOUNDS AS FARNESOID X RECEPTOR MODULATORS". Page/Page column 195; 196. . Retrieved 2020/08/28.
• 2、 Bondarenko,Gavrilova,Murodov,Zefirov,Zyk. "Transformations of gem-dichloroarylcyclopropanes in the reaction with NOCl·2SO3. Synthesis of 3-aryl-5-chloroisoxazoles". . p. 186 - 194. Retrieved 2013/07/25.