68496-88-8

Basic information

• Product Name: ethyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate
• Synonyms: ethyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate
• CAS NO: 68496-88-8
• Molecular Weight: 252.657
• Mol File: 68496-88-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: ethyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate(68496-88-8)
• EPA Substance Registry System: ethyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate(68496-88-8)

Safety Data

• Hazardous Substances Data: 68496-88-8(Hazardous Substances Data)

Upstream product

• 7335-27-5 ethyl 4-chlorobenzoate 
• 104-88-1 4-chlorobenzaldehyde 
• 99-91-2 para-chloroacetophenone 
• 7099-88-9 4-chlorophenylglyoxylic acid 
• 4755-77-5 Ethyl oxalyl chloride 
• 536-40-3 4-chlorobenzoic acid hydrazide 

Downstream Products

• 23289-10-3 2-(4-chlorophenyl)-1,3,4-oxadiazole 
• 1173178-65-8 4-{5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl}benzonitrile 
• 1354791-56-2 (5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)(3-(4-((dimethylamino)methyl)phenoxy)azetidin-1-yl)methanone 
• 1354791-20-0 (5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)(3-(4-(pyrrolidin-1-ylmethyl)phenoxy)azetidin-1-yl)methanone 
• 1254035-95-4 (5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)(3-hydroxyazetidin-1-yl)methanone 

Relevant articles and documents

Design, Synthesis, and Study of the Insecticidal Activity of Novel Steroidal 1,3,4-Oxadiazoles

A series of novel steroidal derivatives with a substituted 1,3,4-oxadiazole structure was designed and synthesized, and the target compounds were evaluated for their insecticidal activity against five aphid species. Most of the tested compounds exhibited potent insecticidal activity against Eriosoma lanigerum (Hausmann), Myzus persicae, and Aphis citricola. Compounds 20g and 24g displayed the highest activity against E. lanigerum, showing LC50 values of 27.6 and 30.4 μg/mL, respectively. Ultrastructural changes in the midgut cells of E. lanigerum were detected by transmission electron microscopy, indicating that these steroidal oxazole derivatives might exert their insecticidal activity by destroying the mitochondria and nuclear membranes in insect midgut cells. Furthermore, a field trial showed that compound 20g exhibited effects similar to those of the positive controls chlorpyrifos and thiamethoxam against E. lanigerum, reaching a control rate of 89.5% at a dose of 200 μg/mL after 21 days. We also investigated the hydrolysis and metabolism of the target compounds in E. lanigerum by assaying the activities of three insecticide-detoxifying enzymes. Compound 20g at 50 μg/mL exhibited inhibitory action on carboxylesterase similar to the known inhibitor triphenyl phosphate. The above results demonstrate the potential of these steroidal oxazole derivatives to be developed as novel pesticides.

Photoredox Catalysis Enables Decarboxylative Cyclization with Hypervalent Iodine(III) Reagents: Access to 2,5-Disubstituted 1,3,4-Oxadiazoles

A novel approach to 2,5-disubstituted 1,3,4-oxadiazoles derivatives via a decarboxylative cyclization reaction by photoredox catalysis between commercially available α-oxocarboxylic acids and hypervalent iodine(III) reagent is described. This powerful transformation involves the coupling reaction between two different kinds of radical species and the formation of C-N and C-O bonds.

Oxidation of sp3C—H bonds in N-alkylhydrazides: Access to 2,5-disubstituted 1,3,4-oxadiazole derivatives

The oxidation of sp3C[sbnd]H bonds in N-alkylhydrazides was achieved en route to the efficient synthesis of a broad series of 1,3,4-oxadiazoles. Mechanistic studies have revealed that N-acylhydrazone is a key intermediate in this catalytic transformation.