1722-18-5

Basic information

• Product Name: 1,3,5-Triazine, 2-phenyl- (9CI)
• Synonyms: 1,3,5-Triazine, 2-phenyl- (9CI);Phenyl-1,3,5-triazine;1,3,5-Triazine,2-phenyl-
• CAS NO: 1722-18-5
• Molecular Formula: C₉H₇N₃
• Molecular Weight: 157.17198
• Product Categories: PYRIMIDINE;QUINAZOLINE
• Mol File: 1722-18-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 341.822 °C at 760 mmHg
• Flash Point: 163.713 °C
• Appearance: /
• Density: 1.17 g/cm³
• Vapor Pressure: 0.000155mmHg at 25°C
• Refractive Index: 1.586
• CAS DataBase Reference: 1,3,5-Triazine, 2-phenyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Triazine, 2-phenyl- (9CI)(1722-18-5)
• EPA Substance Registry System: 1,3,5-Triazine, 2-phenyl- (9CI)(1722-18-5)

Safety Data

• Hazardous Substances Data: 1722-18-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 1470, 1959 DOI: 10.1021/ja01515a047The Journal of Organic Chemistry, 26, p. 2784, 1961 DOI: 10.1021/jo01066a037

InChI:InChI=1/C9H7N3/c1-2-4-8(5-3-1)9-11-6-10-7-12-9/h1-7H

Upstream product

• 290-87-9 1,3,5-Triazine 
• 1670-14-0 benzamidine monohydrochloride 
• 618-39-3 benzamidin 
• 74466-89-0 5-Phenyl-1,2,4-thiadiazole 
• 623-49-4 ethyl cyanoformate 
• 6313-33-3 formamidine hydrochloride 
• 15067-64-8 2,4-bis(methylthio)-6-phenyl-1,3,5-triazine 

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.