28386-89-2

Basic information

• Product Name: 2-benzyl-5-phenyl-2H-tetrazole
• Synonyms: 2-benzyl-5-phenyl-2H-tetraazole; 2-Benzyl-5-phenyl-2H-tetrazole; 2H-tetrazole, 5-phenyl-2-(phenylmethyl)-
• CAS NO: 28386-89-2
• Molecular Formula: C₁₄H₁₂N₄
• Molecular Weight: 236.2719
• Mol File: 28386-89-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 430.3°C at 760 mmHg
• Flash Point: 214°C
• Density: 1.19g/cm³
• Vapor Pressure: 1.31E-07mmHg at 25°C
• Refractive Index: 1.656
• CAS DataBase Reference: 2-benzyl-5-phenyl-2H-tetrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-benzyl-5-phenyl-2H-tetrazole(28386-89-2)
• EPA Substance Registry System: 2-benzyl-5-phenyl-2H-tetrazole(28386-89-2)

Safety Data

• Hazardous Substances Data: 28386-89-2(Hazardous Substances Data)

Upstream product

• 18039-42-4 5-Phenyl-1H-tetrazole 
• 100-39-0 benzyl bromide 
• 620-05-3 iodomethylbenzene 
• 5532-86-5 benzyl cyanoformate 
• 100-47-0 benzonitrile 
• 100-52-7 benzaldehyde 
• 555-96-4 Benzylhydrazine 
• 13211-11-5 benzaldehyde benzylhydrazone 
• 100-46-9 benzylamine 
• 18039-42-4 5-phenyl-2H-1,2,3,4-tetrazole 
• 100-51-6 benzyl alcohol 
• 108-88-3 toluene 

Relevant articles and documents

Alkylation of 5-Substituted 1 H-Tetrazoles via the Diazotization of Aliphatic Amines

A new alkylation reaction of monosubstituted tetrazoles via the diazotization of aliphatic amines is reported. This method enables preferential formation of 2,5-disubstituted tetrazoles. A one-pot 1,3-dipolar cycloaddition/diazotization sequence starting from widely available nitriles is also described. Azide residues are quenched in the second step with the nitrite reagent, thus limiting the intrinsic risk associated with trimethylsilyl azide. The reaction conditions were compatible with several functional groups, including thiocyanates, which afford preferentially disubstituted 2-alkyl-5-(substituted-thio)tetrazoles.

Application of Photoclick Chemistry for the Synthesis of Pyrazoles via 1,3-Dipolar Cycloaddition between Alkynes and Nitrilimines Generated In Situ

The photochemical extrusion of gaseous nitrogen from 2,5-disubstituted tetrazoles to generate reactive nitrilimines in situ represents an efficient and attractive way to form dipoles that can be used to provide useful chemicals via 1,3-dipolar cycloadditions. The concept of “photoclick chemistry” already inspired numerous researchers, who exploited photochemical processes involving alkenes for the synthesis of adducts or the functionalization of biocompatible materials. The approach requires bioorthogonality, ease of access to the starting materials and operational simplicity. We report herein our investigations toward a photoclick reaction involving 2,5-disubstituted tetrazoles and alkynes as the dipolarophile for the synthesis of pyrazole derivatives. In addition to the numerous reports recently published on the synthesis of pyrazoles, we wish to add to the list a photochemical procedure that represents a mild and atom-economical alternative. Moreover, considering that such nitrilimines precursors can be accessed in one step from inexpensive and abundant starting materials and given the commercial availability of a broad spectrum of alkynes, we examined the scope of the photoclick reaction with respect to reactive partners, enabling the synthesis of a library of useful heteroaromatics.

Transition-metal-free direct alkylation of aryl tetrazoles via intermolecular oxidative C-N formation

A transition-metal-free synthetic approach for constructing alkylated aryl tetrazoles has been developed using n-Bu4NI as the catalyst and t-BuOOH as the oxidant. It involves the direct C-N bond formation through sp3 C-H activation. A wide range of benzylic C-H substrates (or alkyl ethers) and aryl tetrazoles undergo this reaction smoothly to deliver the corresponding products in good yields.