1134-56-1

Basic information

• Product Name: 2-ethoxy-5-phenyl-1,3,4-oxadiazole
• Synonyms: 2-Ethoxy-5-phenyl-1,3,4-oxadiazole
• CAS NO: 1134-56-1
• Molecular Formula: C₁₀H₁₀N₂O₂
• Molecular Weight: 190.1986
• Mol File: 1134-56-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 295°C at 760 mmHg
• Flash Point: 132.2°C
• Density: 1.156g/cm³
• Vapor Pressure: 0.00275mmHg at 25°C
• Refractive Index: 1.527
• CAS DataBase Reference: 2-ethoxy-5-phenyl-1,3,4-oxadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ethoxy-5-phenyl-1,3,4-oxadiazole(1134-56-1)
• EPA Substance Registry System: 2-ethoxy-5-phenyl-1,3,4-oxadiazole(1134-56-1)

Safety Data

• Hazardous Substances Data: 1134-56-1(Hazardous Substances Data)

Upstream product

• 59105-38-3 2-oxo-5-phenyl-2λ⁴-[1,2,3,4]oxathiadiazole-3-carboxylic acid ethyl ester 
• 817-87-8 ethyl azidocarbonate 
• 100-47-0 benzonitrile 
• 55084-85-0 5-phenyl-tetrazole-2-carboxylic acid ethyl ester 
• 42157-97-1 1-bromo-1-phenyl-nitromethane 
• 4114-31-2 ethylhydrazine carboxylate 
• 611-73-4 Benzoylformic acid 
• 1972-28-7 diethylazodicarboxylate 
• 4231-62-3 1-benzoyl-1H-benzotriazole 
• 1199-02-6 5-phenyl-3H-[1,3,4]oxadiazol-2-one 
• 100-52-7 benzaldehyde 
• 78-09-1 orthocarbonic acid tetraethyl ester 
• 613-94-5 benzoic acid hydrazide 
• 16208-36-9 ethyl 3-benzylidenecarbazate 

Downstream Products

• 27643-12-5 4-benzyl-2-phenyl-Δ²-1,3,4-oxadiazolin-5-one 
• 1199-02-6 5-phenyl-3H-[1,3,4]oxadiazol-2-one 
• 21816-80-8 2-phenyl-4-ethyl-1,3,4-oxadiazol-5(4H)-one 
• 879-60-7 3-methyl-5-phenyl-1,3,4-oxadiazol-2(3H)-one 
• 55084-87-2 2-phenyl-4-isobutyl-1,3,4-oxadiazol-5(4H)-one 
• 725-12-2 2,5-bis-(phenyl)-1,3,4-oxadiazole 

Relevant articles and documents

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Electrochemical Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from α-Keto Acids and Acylhydrazines Under Mild Conditions

1,3,4-Oxadiazoles are a kind of useful heterocycles which can be frequently found in materials and bioactive molecules. In this study, intermolecular electrochemical cyclization between α-keto acids and acylhydrazines has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles with the yield up to 91 %. This transformation can be run under mild reaction conditions in the absence of external oxidant, base and transition metal catalyst. Both symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles could be prepared according to the careful choice of the substrate combination. Gram scale synthesis also illustrates the potential application of this protocol in large preparation.

A convergent synthesis of 1,3,4-oxadiazoles from acyl hydrazides under semiaqueous conditions

The 1,3,4-oxadiazole is an aromatic heterocycle valued for its low-lipophilicity in drug development. Substituents at the 2- and/or 5-positions can modulate the heterocycle's electronic and hydrogen bond-accepting capability, while exploiting its use as a carbonyl bioisostere. A new approach to 1,3,4-oxadiazoles is described wherein α-bromo nitroalkanes are coupled to acyl hydrazides to deliver the 2,5-disubstituted oxadiazole directly, avoiding a 1,2-diacyl hydrazide intermediate. Access to new building blocks of oxadiazole-substituted secondary amines is improved by leveraging chiral α-bromo nitroalkane or amino acid hydrazide substrates. The non-dehydrative conditions for oxadiazole synthesis are particularly notable, in contrast to alternatives reliant on highly oxophilic reagents to effect cyclization of unsymmetrical 1,2-diacyl hydrazides. The mild conditions are punctuated by the straightforward removal of co-products by a standard aqueous wash.