90418-03-4

Basic information

• Product Name: 5-methyl-3-phenyl-1,2,4-thiadiazole
• Synonyms: 5-methyl-3-phenyl-1,2,4-thiadiazole
• CAS NO: 90418-03-4
• Molecular Weight: 176.242
• Mol File: 90418-03-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 5-methyl-3-phenyl-1,2,4-thiadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methyl-3-phenyl-1,2,4-thiadiazole(90418-03-4)
• EPA Substance Registry System: 5-methyl-3-phenyl-1,2,4-thiadiazole(90418-03-4)

Safety Data

• Hazardous Substances Data: 90418-03-4(Hazardous Substances Data)

Upstream product

• 3663-37-4 3-phenyl-1,2,4-oxadiazol-5-amine 
• 62-55-5 thioacetamide 
• 50483-77-7 3-Methyl-5-phenyl-1,2,4-thiadiazole 
• 24255-23-0 5-chloro-3-phenyl-[1,2,4]thiadiazole 
• 92580-75-1 (3-phenyl-[1,2,4]thiadiazol-5-yl)-malonic acid diethyl ester 

Downstream Products

• 95953-10-9 3,3'-diphenyl-5,5'-(2,2'-p-phenylene-divinyl)-bis-[1,2,4]thiadiazole 
• 94328-46-8 5-(3-nitro-styryl)-3-phenyl-[1,2,4]thiadiazole 
• 92858-94-1 5-(4-nitro-styryl)-3-phenyl-[1,2,4]thiadiazole 
• 94205-90-0 3-phenyl-5-styryl-[1,2,4]thiadiazole 
• 92868-03-6 4-[2-(3-phenyl-[1,2,4]thiadiazol-5-yl)-vinyl]-phenol 
• 78061-84-4 5-(2-oxopropyl)-3-phenyl-1,2,4-thiadiazole 
• 92576-05-1 1-(3-phenyl-[1,2,4]thiadiazol-5-yl)-butan-2-one 
• 92868-01-4 1-phenyl-2-(3-phenyl-[1,2,4]thiadiazol-5-yl)-ethanone 
• 91955-70-3 2-oxo-3-(3-phenyl-[1,2,4]thiadiazol-5-yl)-propionic acid ethyl ester 
• 93873-67-7 N,N-dimethyl-4-[2-(3-phenyl-[1,2,4]thiadiazol-5-yl)-vinyl]-aniline 
• 90322-93-3 3-phenyl-[1,2,4]thiadiazole-5-carbaldehyde oxime 
• 94573-58-7 5-(4-methyl-styryl)-3-phenyl-[1,2,4]thiadiazole 
• 96955-70-3 1-(3-phenyl-[1,2,4]thiadiazol-5-ylmethyl)-pyridinium; iodide 

Relevant articles and documents

Photochemistry of phenyl-substituted 1,2,4-thiadiazoles. 15N-labeling studies

Irradiation of 5-phenyl-1,2,4-thiadiazole (6) resulted in the formation of benzonitrile (5), 3-phenyl-1,2,4-thiadiazole (4), phenyl- and diphenyl-1,3,5-triazines (7 and 8), and a trace quantity of diphenyl-1,2,4-thiadiazole (9). The formation of 4, 5, 7, and 8 can be explained in terms of photoinduced electrocyclic ring closure resulting in the formation of an intermediate 4-phenyl-1,3-diaza-5-thiabicyclo[2.1.0]pentene. 15N-labeling experiments revealed that sulfur can undergo sigmatropic shifts around all four sides of the diazetine ring. Thus, irradiation of 6-4-15N led to the formation of 6-2-15N and an equimolar mixture of 4-2-15N and 4-4-15N. The thiabicyclo[2.1.0]pentene intermediate is also suggested to undergo sulfur elimination resulting in the formation of phenyldiazacyclobutadiene, which can undergo complete fragmentation to benzonitrile or [4+2] cycloaddition leading to unstable tricyclic adducts, the suggested precursors of the 1,3,5-triazine products 7 and 8. The observed 15N distribution in 7 and 8 is consistent with this mechanism. Irradiation of 4 led only to the formation of 5. 15N-labeling experiments show that 4 does not undergo electrocyclic ring closure but reacts exclusively by photofragmentation of the thiadiazole ring.