3-(4-CHLOROPHENYL)-5(4H)-ISOXAZOLONE

Base Information

• Chemical Name: 3-(4-CHLOROPHENYL)-5(4H)-ISOXAZOLONE
• CAS No.: 25755-85-5
• Molecular Formula: C9H6 Cl N O2
• Molecular Weight: 195.605
• Hs Code.: 2934999090
• Mol file: 25755-85-5.mol

Synonyms:2-Isoxazolin-5-one,3-(p-chlorophenyl)- (6CI,8CI); 3-(4-Chlorophenyl)-2-isoxazolin-5-one

Chemical Property of 3-(4-CHLOROPHENYL)-5(4H)-ISOXAZOLONE

Chemical Property:

• PSA: 38.66000
• LogP: 1.42660

Purity/Quality:

99%min ^*data from raw suppliers

3-(4-CHLOROPHENYL)-4,5-DIHYDRO-1,2-OXAZOL-5-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-(4-CHLOROPHENYL)-5(4H)-ISOXAZOLONE

There total 6 articles about 3-(4-CHLOROPHENYL)-5(4H)-ISOXAZOLONE 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: 61.0%

ethyl (4-chlorobenzoyl)acetate (2881-63-2) → 3-(4-chlorophenyl)isoxazol-5-(4H)-one (25755-85-5)

Guidance literature:

With hydroxylamine hydrochloride; In ethanol; water; Heating;

DOI:10.1071/CH99075

Reference yield:

para-chloroacetophenone (99-91-2) → 3-(4-chlorophenyl)isoxazol-5-(4H)-one (25755-85-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / 60 °C

2: hydroxylamine hydrochloride / ethanol / Reflux

With hydroxylamine hydrochloride; sodium hydride; In ethanol;

DOI:10.1016/j.tetlet.2014.09.129

Reference yield:

para-chloroacetophenone (99-91-2) + carbonic acid dimethyl ester (616-38-6) → 3-(4-chlorophenyl)isoxazol-5-(4H)-one (25755-85-5)

Guidance literature:

para-chloroacetophenone; With sodium hydride; In toluene; at 20 ℃; for 0.5h;

carbonic acid dimethyl ester; In toluene; at 110 ℃; for 12h; Further stages;

DOI:10.1021/acs.joc.9b01585

upstream raw materials:

carbon dioxide

4-chloroacetophenone oxime

ethyl (4-chlorobenzoyl)acetate

para-chloroacetophenone

Downstream raw materials:

2-acetyl-3-(4-chlorophenyl)isoxazol-5(2H)-one

5-Bromodifluoromethoxy-3-(4-chlorophenyl)isoxazole

3-(4-Chlorophenyl)-5-difluoromethoxyisoxazole

3-(4-chlorophenyl)-5-methoxyisoxazole

Refernces

• 1、 Zhu, Yi-Ming,Xu, Pei,Wang, Shun-Yi,Ji, Shun-Jun. "Palladium catalyzed insertion reaction of isocyanides with 3-arylisoxazol-5(4 H)-ones: Synthesis of 4-aminomethylidene isoxazolone derivates". . p. 11007 - 11013. Retrieved 2019/09/30.
• 2、 Vereshchagin, Anatoly N.,Elinson, Michail N.,Korshunov, Alexander D.,Anisina, Yuliya E.,Novikov, Roman A.,Goloveshkin, Alexander S.,Bushmarinov, Ivan S.,Zlotin, Sergey G.,Egorov, Mikhail P.. "Stereoselective Michael Halogenation Initiated Ring Closure (MHIRC) Synthesis of Spirocyclopropanes from Benzylidenemalononitriles and 3-Arylisoxazol-5(4H)-ones". . p. 2489 - 2493. Retrieved 2016/10/21.