132401-91-3

Basic information

• Product Name: 3-(4-chlorophenyl)-1,4,2-dioxazol-5-one
• Synonyms: 3-(4-chlorophenyl)-1,4,2-dioxazol-5-one
• CAS NO: 132401-91-3
• Molecular Weight: 197.578
• Mol File: 132401-91-3.mol
• Article Data: 27

Chemical Properties

• CAS DataBase Reference: 3-(4-chlorophenyl)-1,4,2-dioxazol-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-chlorophenyl)-1,4,2-dioxazol-5-one(132401-91-3)
• EPA Substance Registry System: 3-(4-chlorophenyl)-1,4,2-dioxazol-5-one(132401-91-3)

Safety Data

• Hazardous Substances Data: 132401-91-3(Hazardous Substances Data)

Upstream product

• 75-44-5 phosgene 
• 1613-88-3 4-chloro-N-hydroxybenzamide 
• 10507-69-4 4-methoxybenzohydroxamic acid 
• 530-62-1 1,1'-carbonyldiimidazole 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 10364-95-1 1-(4-chloro-benzoyl)-1H-imidazole 
• 74-11-3 para-chlorobenzoic acid 
• 122-01-0 4-chloro-benzoyl chloride 

Downstream Products

• 128258-86-6 4-methyl-5-methoxy-2-(4-chlorophenyl)-2-oxazoline 
• 54573-19-2 4,4-dimethyl-5-methoxy-2-(4-chlorophenyl)-2-oxazoline 
• 104-12-1 p-chlorphenylisocyanate 
• 1581756-86-6 4-chloro-N-[2-(pyridin-2-yl)phenyl]benzamide 
• 83800-99-1 2-(4-chlorophenyl)-4-methoxyquinazoline 
• 119-61-9 benzophenone 
• 1229610-04-1 2-(4-chloro-phenyl)-4-phenyl-quinazoline 
• 91-01-0 1,1-Diphenylmethanol 
• 59524-98-0 2-(4-chlorophenyl)-4-ethoxyquinazoline 
• 1373758-53-2 2-(4-chlorophenyl)-5-(4-ethoxyphenyl)oxazole 
• 134227-60-4 2-(4-chlorophenyl)-5-phenyl-4,5-dihydro-1,3-oxazole 
• 66535-86-2 2-(4-chloro-phenyl)-[1,2,4]triazolo[5,1-a]isoquinoline 
• 6833-15-4 4-chlorobenzanilide 
• 962-08-3 N-(4-chlorophenyl)-3-oxo-3-phenylpropanamide 

Relevant articles and documents

Rhodium(iii)-catalyzed diamidation of olefins: Via amidorhodation and further amidation

Rh(iii)-catalyzed synthesis of vicinal diamides has been realized via elaboration of an authenticated Rh-C(sp3) species generated via initial intramolecular amidorhodation of olefins. The second amidation was achieved using both electrophilic and nucleophilic amidating reagents. The reactions proceeded under mild conditions with good yield, broad substrate scope, and excellent functional-group tolerance.

Cu(II)-Catalyzed C-H Amidation/Cyclization of Azomethine Imines with Dioxazolones via Acyl Nitrenes: A Direct Access to Diverse 1,2,4-Triazole Derivatives

We report a Cu(II)-catalyzed C-H amidation/cyclization of azomethine imines with dioxazolones as acyl nitrene transfer reagents under additive-and ligand-free conditions. An array of 1,2,4-triazolo[1,5-a]pyridine derivatives were afforded in moderate to good yields with excellent functional group tolerance. In addition, scale-up reaction and photoluminescence properties were discussed.

Thioether-Directed NiH-Catalyzed Remote γ-C(sp3)-H Hydroamidation of Alkenes by 1,4,2-Dioxazol-5-ones

A NiH-catalyzed thioether-directed cyclometalation strategy is developed to enable remote methylene C-H bond amidation of unactivated alkenes. Due to the preference for five-membered nickelacycle formation, the chain-walking isomerization initiated by the NiH insertion to an alkene can be terminated at the γ-methylene site remote from the alkene moiety. By employing 2,9-dibutyl-1,10-phenanthroline as the ligand and dioxazolones as the reagent, the amidation occurs at the γ-C(sp3)-H bonds to afford the amide products in up to 90% yield (>40 examples) with remarkable regioselectivity (up to 24:1 rr).

Interweaving Visible-Light and Iron Catalysis for Nitrene Formation and Transformation with Dioxazolones

Herein, visible-light-driven iron-catalyzed nitrene transfer reactions with dioxazolones for intermolecular C(sp3)-N, N=S, and N=P bond formation are described. These reactions occur with exogenous-ligand-free process and feature satisfactory to excellent yields (up to 99 %), an ample substrate scope (109 examples) under mild reaction conditions. In contrast to intramolecular C?H amidations strategies, an intermolecular regioselective C?H amidation via visible-light-induced nitrene transfer reactions is devised. Mechanistic studies indicate that the reaction proceeds via a radical pathway. Computational studies show that the decarboxylation of dioxazolone depends on the conversion of ground sextet state dioxazolone-bounding iron species to quartet spin state via visible-light irradiation.