1090-82-0

Basic information

• Product Name: 2-(4-nitrophenyl)-5-phenyl-[1,3,4]oxadiazole
• Synonyms: 2-(4-nitrophenyl)-5-phenyl-[1,3,4]oxadiazole
• CAS NO: 1090-82-0
• Molecular Formula: C₁₄H₉N₃O₃
• Molecular Weight: 267.23956
• Mol File: 1090-82-0.mol
• Article Data: 47

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-nitrophenyl)-5-phenyl-[1,3,4]oxadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-nitrophenyl)-5-phenyl-[1,3,4]oxadiazole(1090-82-0)
• EPA Substance Registry System: 2-(4-nitrophenyl)-5-phenyl-[1,3,4]oxadiazole(1090-82-0)

Safety Data

• Hazardous Substances Data: 1090-82-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 90, p. 5626, 1968 DOI: 10.1021/ja01022a066

Upstream product

• 6781-65-3 N'-benzoyl-4-nitrobenzohydrazide 
• 18039-42-4 5-Phenyl-1H-tetrazole 
• 122-04-3 4-nitro-benzoyl chloride 
• 532-55-8 Benzoyl isothiocyanate 
• 16687-60-8 5-(4-nitrophenyl)-2H-tetrazole 
• 902-47-6 p-nitrobenzoic anhydride 
• 4402-22-6 N,N'-bis-(4-nitro-benzoyl)-hydrazine 
• 134022-08-5 2-(4-nitrophenyl)-3-acetyl-5-phenyl-2,3-dihydro-1,3,4-oxadiazole 
• 93-58-3 benzoic acid methyl ester 
• 100-52-7 benzaldehyde 
• 636-97-5 N-amino-(4-nitrophenyl)carboxamide 
• 613-94-5 benzoic acid hydrazide 
• 555-16-8 4-nitrobenzaldehdye 
• 59394-91-1 (E)-N′-(4-nitrobenzylidene)benzohydrazide 

Downstream Products

• 17012-75-8 2-(3-nitrophenyl)-5-(4-nitrophenyl)-1,3,4-oxadiazole 
• 74415-24-0 2-(2-nitrophenyl)-5-(4-nitrophenyl)-1,3,4-oxadiazole 
• 1044-49-1 bis-(4-nitro-phenyl)-[1,3,4]oxadiazole 
• 1874-33-5 4-(5-phenyl-1,3,4-oxadiazol-2-yl)benzonitrile 
• 2003-84-1 2-Phenyl-5-(4-carbamoyl-phenyl)-1,3,4-oxadiazol 
• 925102-99-4 4-oxo-4(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenylamino)butanoic acid 
• 610257-94-8 4-fluoro-N-(4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl)benzamide 
• 356791-78-1 4-methyl-N-(4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl)benzamide 
• 356792-11-5 4-methoxy-N-(4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl)benzamide 
• 357154-78-0 4-nitro-N-(4-(5-phenyl-1,3,4-oxadiazole-2-yl)phenyl)benzamide 
• 709010-11-7 2-chloro-N-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]benzamide 
• 23133-32-6 1-acetoxy-4-(5-phenyl-[1,3,4]oxadiazol-2-yl)-benzene 
• 842-79-5 2-(4-methoxy-phenyl)-5-phenyl-[1,3,4]oxadiazole 
• 23133-34-8 2-(4-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazole 

Relevant articles and documents

Zirconium(IV) chloride mediated cyclodehydration of 1,2-diacylhydrazines: A convenient synthesis of 2,5-diaryl 1,3,4-oxadiazoles

Zirconium(IV) chloride was invented as a mild catalyst for the cyclodehydration of 1,2-diacylhydrazines. Efficient synthesis of several 2,5-disubstituted 1,3,4-oxadiazoles is reported.

One-pot, three component synthesis of 2,5-disubstituted 1,3,4-oxadiazoles catalyzed by heteropolyacid

H6[PMo9V3O40] was used as an efficient catalyst for the preparation of 1-aroyl-2-arylidene hydrazines. 2,5-Disubstituted 1,3,4-oxadiazoles have been synthesized by oxidation of 1-aroyl-2-arylidene hydrazines with CrO3 in excellent yields.

Experimental and Theoretical Studies on the Mechanism of DDQ-Mediated Oxidative Cyclization of N-Aroylhydrazones

The controversial single-electron-transfer process, frequently proposed in many 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated reactions, was investigated experimentally and theoretically using the oxidative cyclization of aroylhydrazone with DDQ. DDQ-mediated oxadiazole formation involves several processes, including cyclization to form an oxadiazole ring and N-H bond cleavage, either by proton, hydride, or hydrogen atom transfer. The detailed mechanistic study using the M06-2X density functional theory, and the 6-31+G(d,p) basis set, suggests that the pathways involving radical ion pair (RIP) intermediates, which resulted from single-electron transfer (SET), were found to be energetically nearly identical to the pathway without the SET. The substituent-dependent reactivity of oxadiazole formation was consistent with the free energy profiles of both pathways, with or without the SET. This result indicates that in addition to the electron-transfer pathway, the nucleophilic addition/elimination pathway for DDQ should be considered as a possible mechanism of the oxidative transformation reaction using DDQ.

Study on DDQ-promoted synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles from acid hydrazides and aldehydes

A facile stepwise synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles proceeding via oxidative cyclization of N-acylhydrazones is reported. The reaction is efficiently promoted by 2, 3-dichloro-5, 6-dicyano-1, 4- benzoquinone (DDQ) to afford the desired products mostly in high yields and in relatively short times. The final 1, 3, 4-oxadiazole derivatives are also synthesized directly from acid hydrazides and aldehydes in a one-pot procedure. The substrate scope and limitations of the reported transformation are discussed in detail.

Ligand-free copper(0) catalyzed direct C-H arylation of 1,2,4-triazoles and 1,3,4-oxadiazoles with aryl iodides in PEG-400

A ligand-free copper catalyzed approach has been developed to the synthesis of 3,4,5-triaryl-1,2,4-triazoles and 2,5-diaryl-1,3,4-oxadiazoles by the direct arylation of corresponding 3,4-diaryl-1,2,4-triazoles and 2-aryl-1,3,4-oxadiazoles with aryl iodides using PEG-400 as reaction medium. The procedure is experimentally simple and free from addition of external chelating ligands or co-catalysts.