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Usage

Uses

Used in Pharmaceutical Industry:
2-Benzyl-1,3,4-oxadiazole serves as an intermediate in the synthesis of various pharmaceuticals due to its potential biological activities. It is used as a building block for the development of new drugs with antioxidant, anticancer, and anti-inflammatory properties, contributing to the treatment of various diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical industry, 2-benzyl-1,3,4-oxadiazole is utilized as an intermediate in the synthesis of agrochemicals, such as pesticides and herbicides. Its unique structure and reactivity enable the creation of effective compounds for crop protection and management.
Used in Material Science:
2-Benzyl-1,3,4-oxadiazole's unique structure and reactivity make it a valuable component in the development of new materials and functional molecules. It is used in the creation of advanced materials with specific properties, such as conductivity, magnetism, or luminescence, for various applications in material science.
Used in Chemical Research:
As a versatile chemical compound, 2-benzyl-1,3,4-oxadiazole is employed in chemical research for the exploration of new reactions, synthesis methods, and the development of novel compounds with potential applications in various fields, including medicine, agriculture, and material science.

InChI:InChI=1/C9H8N2O/c1-2-4-8(5-3-1)6-9-11-10-7-12-9/h1-5,7H,6H2

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 937-39-3 2-phenylacetylhydrazine 
• 149-73-5 trimethyl orthoformate 
• 1338916-77-0 1,1'-diphenylthiodiacetic acid dihydrazide 
• 101-97-3 Ethyl 2-phenylethanoate 
• 4695-09-4 α-mercaptophenylacetic acid 
• 611-71-2 MANDELIC ACID 
• 16201-52-8 2-mercapto-2-phenylacetic acid methyl ester 
• 90006-97-6 α-mercaptophenylacetic acid hydrazide 
• 4870-65-9 2-bromophenylacetic acid 
• 101-41-7 benzeneacetic acid methyl ester 
• 103-82-2 phenylacetic acid 

Downstream Products

• 1025984-46-6 {1-[(5-benzyl-[1,3,4]oxadiazol-2-yl)-hydroxy-methyl]-2-methyl-propyl}-carbamic acid tert-butyl ester 
• 140-29-4 phenylacetonitrile 
• 1398814-78-2 2-benzyl-1,3,4-oxadiazolyldiphenylphosphine 
• 1280732-66-2 (5-benzyl-[1,3,4]oxadiazol-2-yl)-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-methanol 

Relevant academic research and scientific papers

Reactions of α-mercaptocarboxylic acid hydrazides with triethyl orthoesters: Synthesis of 1,3,4-thiadiazin-5(6H)-ones and 1,3,4-oxadiazoles

Reactions of α-mercapto-β-phenylpropionic and α-mercaptophenylacetic acid hydrazides with triethyl orthoesters were conducted under N2 in glacial acetic acid and resulted in the formation of two groups of products, derivatives of 1,3,4-thiadiazin-5(6H)-ones and 2-(1-mercaptomethyl)-1,3,4-oxadiazoles. When conducting the same transformations on α-mercaptophenylacetic acid hydrazide in the presence of air, two different products from the 1,3,4-oxadiazole family, the appropriate bis(1,3,4-oxadiazol-2-yl-phenylmethyl) disulfides and 2-benzyl-1,3,4- oxadiazoles, were formed with the liberation of free sulfur. The oxygenated bis(1,3,4-oxadiazol-2-yl-phenylmethyl) disulfides were reduced to the corresponding 2-(1-mercaptomethyl)-1,3,4-oxadiazoles with the use of zinc powder under mild conditions.

The synthesis of bis(1,3,4-oxadiazol-2-yl-phenylmethyl) sulfides and other related 1,3,4-oxadiazoles from 1,1′-diphenylthiodiacetic acid dihydrazide and triethyl orthoesters

Reactions of symmetrical 1,1′-diphenylthiodiacetic acid dihydrazide and triethyl orthoesters in the presence of catalytic amount of glacial acetic acid resulted in the formation of three heterocyclic products: the appropriate bis(1,3,4-oxadiazol-2-yl-phenylmethyl) sulfides, 2-benzyl-1,3,4-oxadiazoles and 2-benzoyl-1,3,4-oxadiazoles. The presence of the latter two compounds is connected with carbon-sulfur fission in the molecule of the starting hydrazide. The identity of the unexpected fission products was confirmed by parallel syntheses of the model 1,3,4-oxadiazoles from phenylacetic acid hydrazide and 2-hydroxymethyl-1,3,4-oxadiazole derivatives.

Greener and rapid access to bio-active heterocycles: one-pot solvent-free synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles

A novel one-pot solvent-free synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles by condensation of acid hydrazide and triethyl orthoalkanates under microwave irradiations is reported. This green protocol was catalyzed efficiently by solid supported NafionNR50 and phosphorus pentasulfide in alumina (P4S10/Al2O3) with excellent yields.

Development of orally active nonpeptidic inhibitors of human neutrophil elastase

5-Amino-2-phenylpyrimidin-6-ones, some of their desamino derivatives, and miscellaneous derivatives were synthesized and biologically evaluated on both in vitro activity and oral activity in an acute hemorrhagic assay. These compounds contained an α-keto-1,3,4-oxadiazole moiety to bind covalently to the Ser-195 hydroxy group of human neutrophil elastase (HNE). Among those tested, compounds 11a-c,e,i-l(F), 11d,e,k(H), 21d,e,k(F), and 21d,e(H) showed a good oral profile. RS-Mixture 3(H) was selected for clinical evaluation based on its oral potency, duration of action, enzyme selectivity, safety profile, and ease of synthesis. Structure -activity relationships (SARs) are discussed.