122503-21-3

Basic information

• Product Name: 3-(4-methoxyphenyl)-5-vinyl-1,2,4-oxadiazole
• Synonyms: 3-(4-methoxyphenyl)-5-vinyl-1,2,4-oxadiazole
• CAS NO: 122503-21-3
• Molecular Weight: 202.213
• Mol File: 122503-21-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3-(4-methoxyphenyl)-5-vinyl-1,2,4-oxadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-methoxyphenyl)-5-vinyl-1,2,4-oxadiazole(122503-21-3)
• EPA Substance Registry System: 3-(4-methoxyphenyl)-5-vinyl-1,2,4-oxadiazole(122503-21-3)

Safety Data

• Hazardous Substances Data: 122503-21-3(Hazardous Substances Data)

Upstream product

• 5373-87-5 4-methoxybenzamidoxime 
• 874-90-8 4-methoxybenzonitrile 
• 814-68-6 acryloyl chloride 
• 3717-21-3 p-methoxyl benzaldoxime 
• 35787-71-4 thianthrene cation radical perchlorate 

Relevant articles and documents

Development of Potent 3-Br-isoxazoline-Based Antimalarial and Antileishmanial Compounds

Starting from the structure of previously reported 3-Br-isoxazoline-based covalent inhibitors of P. falciparum glyceraldehyde 3-phosphate dehydrogenase, and with the intent to improve their metabolic stability and antimalarial activity, we designed and synthesized a series of simplified analogues that are characterized by the insertion of the oxadiazole ring as a bioisosteric replacement for the metabolically labile ester/amide function. We then further replaced the oxadiazole ring with a series of five-membered heterocycles and finally combined the most promising structural features. All the new derivatives were tested in vitro for antimalarial as well as antileishmanial activity. We identified two very promising new lead compounds, endowed with submicromolar antileishmanial activity and nanomolar antiplasmodial activity, respectively, and a very high selectivity index with respect to mammalian cells.

Reactions of Oximes with Thianthrene Cation Radical in Nitrile Solvents. Cycloaddition To Form Oxadiazoles and Deoxygenation To Form Nitriles

Reactions of eight oximes, RCH=NOH (1a, R= C6H5; 1b, R= 4-CH3C6H4; 1c, R= 4-NO2C6H4; 1d, R= 4-CH3OC6H4; 1e, R= 2-CH3OC6H4; 1f, R= 1-naphthyl; 1g, R= C5H11; 1h, R= C4H9), with thianthrene cation radical perchlorate (Th.+ClO4-) in acetonitrile under argon were studied.The major product from the oxime in all cases, but of 1d, was the nitrile, RCN.The anticipated product of oxidative cycloaddition, namely, a 3-R-5-methyl-1,2,4-oxadiazole (2), was obtained in substantial yield (2d, 66percent) only in the case of 1d.An isomeric 5-R-3-methyl-1,2,4-oxadiazole (3) was obtained from some reactions, that is, 3c alone from 1c, and a mixture of 2a and 3a from 1a.Neither 2 nor 3 was obtained in measurable amounts from reactions of 1g and 1h.The aldehyde (RCHO) was obtained in small yields from each reaction.Thianthrene (Th) and thianthrene 5-oxide (ThO) were also major products.Studies with -1b and -1d showed that the oxgen atom in 2 came entirely and in ThO primarily from the oxime.Studies of workup with H218O showed that the workup water was the source of the oxgen atom in RCHO and to a small extent in ThO.Explanations are given for the formation of 2 by a stepwise addition of RCH=NOH.+ (1.+) to solvent nitrile and of 3 by the reaction of solvent nitrile with an oxaziridine cation radical (7, obtained from 1.+).