19226-10-9

Basic information

• Product Name: 3,5-Diphenyl-1,3,4-oxadiazol-2(3H)-one
• Synonyms: 3,5-Diphenyl-1,3,4-oxadiazol-2(3H)-one
• CAS NO: 19226-10-9
• Molecular Formula: C₁₄H₁₀N₂O₂
• Molecular Weight: 0
• Mol File: 19226-10-9.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,5-Diphenyl-1,3,4-oxadiazol-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Diphenyl-1,3,4-oxadiazol-2(3H)-one(19226-10-9)
• EPA Substance Registry System: 3,5-Diphenyl-1,3,4-oxadiazol-2(3H)-one(19226-10-9)

Safety Data

• Hazardous Substances Data: 19226-10-9(Hazardous Substances Data)

Upstream product

• 100-63-0 phenylhydrazine 
• 1199-02-6 5-phenyl-3H-[1,3,4]oxadiazol-2-one 
• 66003-76-7 Diphenyliodonium triflate 
• 613-94-5 benzoic acid hydrazide 
• 591-50-4 iodobenzene 
• 532-96-7 N-benzoyl-N'-phenylhydrazine 
• 98-88-4 benzoyl chloride 
• 156216-46-5 tetrahydro-1-benzoyl-2,4,6-triphenyl-1,2,4,5-tetrazin-3(2H)-one 
• 106538-30-1 N'-ethoxycarbonyl-N'-phenylbenzohydrazide 
• 75-44-5 phosgene 
• 124-38-9 carbon dioxide 
• 588-64-7 benzaldehyde phenylhydrazone 
• 100-52-7 benzaldehyde 
• 13183-09-0 3-phenyl-4-bromosydnone 

Downstream Products

• 34241-53-7 3,3',5,5'-tetraphenyl-2(3H),2'(3'H)-spirobi-1,3,4-thiadiazole 
• 93326-84-2 2,5-diphenyl-3,4-dihydro-2H-pyrazole-3r,4c-dicarboxylic acid anhydride 

Relevant articles and documents

Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts

Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts under mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows utilizing both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). We found that the steric effects in aryl moieties determined the chemoselectivity of N- and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones. Mesityl-substituted diaryliodonium salts demonstrated the high potential as a selective arylation reagent. The structural study suggests that steric accessibility of N-atom in 1,2,4-oxadiazol-5(4H)-ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4-oxadiazol-2(3H)-ones and 1,2,4-oxadiazole-5-thiol. (Figure presented.).

The reaction of sydnones with bromine in acetic anhydride revisited: A new route to 5-substituted-3-aryl-1,3,4-oxadiazol-2(3H)-ones from N-aryl-N-bromocarbonylhydrazines

The reaction of 3-phenylsydnone with bromine in acetic anhydride to form 5-methyl-3-phenyl-1,3,4-oxadiazol-2(3H)-one has been reexamined and improved. A new mechanism involving a bromocarbonylhydrazine species is proposed and its intermediacy is supported

Method for synthesizing 1,3,4-oxadiazole-2-one compounds of oxadiazon and the like by carbon dioxide

The invention discloses a method for synthesizing 1,3,4-oxadiazole-2-one compounds of oxadiazon and the like by carbon dioxide. The method comprises: adding an acyl halide hydrazone raw material and a solvent into a high-pressure autoclave; using alkali and an additive as accelerants, introducing carbon dioxide, and performing a stirring reaction for 6 to 24 hours at a temperature of 0 to 70 DEG C; after finishing the reaction, cooling to the room temperature; slowly releasing the unreacted carbon dioxide; after adding water to dilute reaction liquid, carrying out extraction by ethyl acetate; concentrating to obtain a crude product; purifying by column chromatography to obtain the 1,3,4-oxadiazole-2-one compounds. The method disclosed by the invention uses the carbon dioxide for replacing conventional phosgene and carbon monoxide, is safe and simple to operate, low in toxicity, friendly to the environment, simple and easy for obtaining reaction raw materials and reagents, wide in universality of a type of a reaction substrate, simple in post-processing process, high in target product yield and beneficial to industrial production, and is widely applied in synthesis of pesticides, medicines and natural products.