58737-90-9

Basic information

• Product Name: 2H-1,2,3-Triazole, 4,5-dimethyl-2-phenyl-
• CAS NO: 58737-90-9
• Molecular Formula: C10H11N3
• Molecular Weight: 173.217
• Mol File: 58737-90-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2H-1,2,3-Triazole, 4,5-dimethyl-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1,2,3-Triazole, 4,5-dimethyl-2-phenyl-(58737-90-9)
• EPA Substance Registry System: 2H-1,2,3-Triazole, 4,5-dimethyl-2-phenyl-(58737-90-9)

Safety Data

• Hazardous Substances Data: 58737-90-9(Hazardous Substances Data)

Upstream product

• 24624-00-8 2,3-bis-phenylazo-but-2-ene 
• 67-68-5 dimethyl sulfoxide 
• 138815-29-9 N-Benzoyl-2-phenyl-4,5-dimethyl-1,2,3-triazol-1-imine 
• 15256-65-2 4,5-dimethyl-2-phenyl-1,2,3-triazole-1-oxide 
• 75-36-5 acetyl chloride 
• 2861-48-5 butane-2,3-dione-bis-phenylhydrazone 
• 644-21-3 1-ethyl-1-phenylhydrazine 
• 135636-66-7 butane-2,3-dione mono-oxime 
• 80957-49-9 3-hydroxyomono-2-phenylhydrazonobutane 
• 100-63-0 phenylhydrazine 
• 31400-24-5 Biacetyl Benzoylhydrazone Phenylhydrazone 

Downstream Products

• 90916-86-2 2-(p-nitrophenyl)-4,5-dimethyl-1,2,3-triazole 

Relevant articles and documents

Synthesis of 2-Substituted 1,2,3-Triazoles via an Intramolecular N–N Bond Formation

An efficient synthesis of 2-aryl 1,2,3-triazoles based on an intramolecular N–N bond formation is described. Selective activation of bis-hydrazone at the dimethylamino hydrazone group with MeI forms a mono-hydrazonium species. Treatment of the hydrazonium

Reaction of 2-phenyl substituted 1,2,3-triazol 1-oxides with acylating agents. Preparation of hydroxy- halogen- hydroxymethyl- and chloromethyltriazoles

2-Phenyltriazol 1-oxides react with acetyl chloride producing acetoxy- and chloro-substituted triazoles.The substituents enter the 5 and the 4-position.When these are not accessible the substituents go to lateral positions and to the phenyl group producing acetoxymethyltriazoles and 2-halogenophenyl triazoles.Acetic anhydride reacts reluctantly while trifluoroacetic anhydride is more reactive producing trifluoroacetoxytriazoles.The reactions provide effective routes to hydroxy- and hydroxymethyltriazoles.Several mechanisms among which a cyclic one are operating.

Activation of Exocyclic α-Positions of Azole N-Oxides by O-Silylation

Exocyclic α-positions at immonium ring carbon atoms of pyrazole and 1,2,3-triazole 1-oxides are selectively attacked in a one-pot sequence comprising silylation with iodotrimethylsilane, deprotonation with 1,2,2,6,6-pentamethylpiperidine and allylic substitution of the trimethylsilyloxy group with the iodide ions liberated by the silylation.In this way 3- and 5-iodomethylpyrazoles as well as 4-iodomethyl-1,2,3-triazoles are obtained in good yields.These may be useful for the preparation of heteroarylmethyl derivatives since the iodine atom can be displaced by even weak nucleophiles such as acetate ions.The side chain iodination is complementary to O-alkylation of the N-oxides followed by nucleophilic attack which preferentially takes place at ring carbon atoms.