120337-45-3

Basic information

• Product Name: 1-benzyl-4-phenyl-1,2,4-triazolium chloride
• CAS NO: 120337-45-3
• Molecular Weight: 271.749
• Mol File: 120337-45-3.mol

Chemical Properties

• CAS DataBase Reference: 1-benzyl-4-phenyl-1,2,4-triazolium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-4-phenyl-1,2,4-triazolium chloride(120337-45-3)
• EPA Substance Registry System: 1-benzyl-4-phenyl-1,2,4-triazolium chloride(120337-45-3)

Safety Data

• Hazardous Substances Data: 120337-45-3(Hazardous Substances Data)

Upstream product

• 16227-12-6 1-phenyl-1,3,4-triazole 
• 100-44-7 benzyl chloride 
• 62-53-3 aniline 
• 144091-32-7 1-Benzyl-5-methoxy-4-phenyl-4,5-dihydro-1H-[1,2,4]triazole 

Downstream Products

• 144091-31-6 4-benzyl-1-formyl-1-phenyl-amidrazone 
• 144091-33-8 1-benzyl-1,5-dihydro-4-phenyl-1,2,4-triazole-5-oxide-anion 
• 144091-32-7 1-Benzyl-5-methoxy-4-phenyl-4,5-dihydro-1H-[1,2,4]triazole 

Relevant articles and documents

Kinetics anmd Mechanism of Ring Cleavage of 1-Benzyl-4-phenyl-1,2,4-triazolium Chloride

1-Benzyl-4-phenyl-1,2,4-triazolium chloride (1) is cleaved by aqueous sodium hydroxide to form 4-benzyl-1-formyl-1-phenyl-amidrazone (5), the structure of which is proved by mass spectroscopy.The kinetics of the cleavage reaction are studied by UV spectroscopy in methanol/water 1:1 (v/v) in the presence of Na2CO3/HCl buffer at pH values from 11.64 to 12.61.The reaction obeys a first-order kinetic law.The rate constants do not depend linearly on the hydroxide concentration.This is in coincidence with fast formation of the pseudobase from 1, followed by fast deprotonation to the pseudobase anion, and slow decay to the amidrazone.The pseudobase anion is proved spectroscopically, and its spectroscopically determined pKQOH = 12.7 coincides with that from the kinetic experiments.The equilibrium constant of pseudobase formation pKA = 10.99 is two orders of magnitude higher than that from the azocoupling of 1 which shows that in the azocoupling not the pseudobase but its methyl ether (pKQOMe = 8.7) is active. 4-Benzyl-1-formyl-1-phenyl-amidrazone (5) re-cyclizes in the presence of HCl in MeOH/H2O to form 1.The kinetics of this reaction are also studied.

Azocoupling of Quaternary 1,2,4-Triazolium Salts to Form 5-p-N,N-Dimethylaminophenylazo-1,2,4-triazolium Salts

Quaternary 1,2,4-triazolium salts 1 couple easily with p-N,N-dimethylamino-benzenediazonium salts to form azodyes 3 (5-N,N-dimethylaminophenylazo-1,2,4-triazolium salts), preferably under solid-liquid phase transfer conditions using chloroform or methylene chloride and triethylamine or DABCO.Zwitterionic 1,2,4-triazolium salts (anhydro mercapto hydroxide, anhydro hydroxy hydroxide, and anhydro anilido hydroxide ("nitron")) couple as well.The azodyes - as also well known from industrially used types - absorb in the region of 500 nm and have high extinction coefficients.Substituents in 1-, 3- or 4-position of the triazolium ring exert no clear substituent effects.The quaternary 1,2,4-triazolium salts were synthesized according to standard procedures.