7465-48-7

Basic information

• Product Name: 5,6,7,8-Tetrahydrotetrazolo[1,5-a]pyridine
• Synonyms: 5,6,7,8-Tetrahydrotetrazolo[1,5-a]pyridine;Tetramethylenetetrazole
• CAS NO: 7465-48-7
• Molecular Formula: C₅H₈N₄
• Molecular Weight: 124.1438
• Mol File: 7465-48-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 336°Cat760mmHg
• Flash Point: 157°C
• Appearance: /
• Density: 1.53g/cm³
• Vapor Pressure: 0.000115mmHg at 25°C
• Refractive Index: 1.772
• CAS DataBase Reference: 5,6,7,8-Tetrahydrotetrazolo[1,5-a]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6,7,8-Tetrahydrotetrazolo[1,5-a]pyridine(7465-48-7)
• EPA Substance Registry System: 5,6,7,8-Tetrahydrotetrazolo[1,5-a]pyridine(7465-48-7)

Safety Data

• Hazardous Substances Data: 7465-48-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 1218, 1993 DOI: 10.1055/s-1993-26027

InChI:InChI=1/C5H8N4/c1-2-4-9-5(3-1)6-7-8-9/h1-4H2

Upstream product

• 660-88-8 5-aminopentanoic acid 
• 120-92-3 cyclopentanone 
• 21994-41-2 5-azidopentanenitrile 
• 274-87-3 tetrazolo[1,5-a]pyridine 

Downstream Products

• 954154-12-2 8-benzylidene-5,6,7,8-tetrahydro-tetrazolo[1,5-a]pyridine 
• 926290-89-3 acetic acid phenyl-(5,6,7,8-tetrahydro-tetrazolo[1,5-a]pyridin-8-yl)-methyl ester 
• 32847-45-3 N-(but-3-en-1-yl)cyanamide 

Relevant articles and documents

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Remodeling and Enhancing Schmidt Reaction Pathways in Hexafluoroisopropanol

The effect of carrying out two variations of the Schmidt reaction with ketone electrophiles in hexafluoroisopropanol (HFIP) solvent has been studied. When TMSN3 is reacted with ketones in the presence of triflic acid (TfOH) promoter, tetrazoles are obtained as the major products. This observation is in contrast to established methods, which usually lead to amides or lactams arising from formal NH insertion as the major products. The full product profiles of several examples of this reaction are also reported and found to include mechanistically interesting products (e.g., double ring expansion). Application of TfOH promoter in HFIP was also found to promote the reaction of a hydroxyalkyl azide with a ketone, which affords lactams following nucleophilic opening of initially formed iminium ether more efficiently than previously reported methods. (Chemical Equation Presented).

Preparation of 1,5-fused tetrazoles under solvent-free conditions

A facile and efficient procedure is developed for a one-pot synthesis of fused 1,5-disubstituted tetrazoles from cyclic ketones and sodium azide in the presence of aluminum chloride in solvent-free media. Advantages of this method are chemoselectivity, with high yields in a simple operation, and short reaction time under solvent-free conditions. Copyright Taylor & Francis, Inc.