5-Chloro-3-(4-nitrophenyl)-1,2-oxazole

Base Information

• Chemical Name: 5-Chloro-3-(4-nitrophenyl)-1,2-oxazole
• CAS No.: 142598-83-2
• Molecular Formula: C9H5ClN2O3
• Molecular Weight: 224.603
• DSSTox Substance ID: DTXSID60570597
• Nikkaji Number: J880.767A
• Mol file: 142598-83-2.mol

Synonyms:5-Chloro-3-(4-nitrophenyl)-1,2-oxazole;142598-83-2;3-(4-Nitrophenyl)-5-chloroisoxazole;DTXSID60570597;5-CHLORO-3-(4-NITROPHENYL)ISOXAZOLE

Chemical Property of 5-Chloro-3-(4-nitrophenyl)-1,2-oxazole

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: 238

Purity/Quality:

99.90% ^*data from raw suppliers

5-CHLORO-3-(4-NITROPHENYL)ISOXAZOLE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=NOC(=C2)Cl)[N+](=O)[O-]

Technology Process of 5-Chloro-3-(4-nitrophenyl)-1,2-oxazole

There total 4 articles about 5-Chloro-3-(4-nitrophenyl)-1,2-oxazole 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: 95.0%

2-(4-nitrophenyl)-1,1-dichlorocyclopropane (31913-36-7) → 3-(4-nitrophenyl)-5-chloroisoxazole (142598-83-2)

Guidance literature:

With nitrosyl chloride sulfur trioxide; In dichloromethane; at 20 ℃; for 24h; Reagent/catalyst; Time; Solvent; chemoselective reaction;

DOI:10.1134/S1070428013020024

Reference yield: 85.4%

2-(4-nitrophenyl)-1,1-dichlorocyclopropane (31913-36-7) → 1,1-dichloro-2-(2,4-dinitrophenyl)cyclopropane (181057-90-9) + 4-nitrobenzaldehdye (555-16-8) + 3-(4-nitrophenyl)-5-chloroisoxazole (142598-83-2)

Guidance literature:

With sulfuric acid; nitric acid; at 0 ℃; for 1h; Mechanism; other aryl-substituted cyclopropanes;

Reference yield: 5.0%

2-(4-nitrophenyl)-1,1-dichlorocyclopropane (31913-36-7) → 3-(4-nitrophenyl)-5-chloroisoxazole (142598-83-2) + 4-nitro-benzoic acid (62-23-7)

Guidance literature:

With nitrosonium tetrafluoroborate; In acetonitrile; for 1.5h; Ambient temperature;

DOI:10.1021/jo962297i

upstream raw materials:

2-(4-nitrophenyl)-1,1-dichlorocyclopropane

1,1-dichloro-2-phenylcyclopropane

Downstream raw materials:

5-methoxy-3-(4-nitrophenyl)isoxazole

Refernces

• 1、 Bondarenko, Oksana B.,Garaev, Zaur M.,Komarov, Arseniy I.,Kuznetsova, Lyubov I.,Gutorova, Svetlana V.,Skvortsov, Dmitry A.,Zyk, Nikolai V.. "Nitrosylsulfuric acid in the synthesis of 5-chloroisoxazoles from 1,1-dichlorocyclopropanes". . p. 419 - 420. Retrieved 2019/08/20.
• 2、 Lin,Kuo,Yang. "Reaction of halogenated cyclopropanes and nitrosyl cation: Preparation of isoxazoles". . p. 5229 - 5231. Retrieved 2007/10/03.