14506-41-3

Basic information

• Product Name: phenyl(2H-tetrazol-5-yl)methanone
• CAS NO: 14506-41-3
• Molecular Formula: C₈H₆N₄O
• Molecular Weight: 174.1594
• Mol File: 14506-41-3.mol

Chemical Properties

• Boiling Point: 381.2°C at 760 mmHg
• Flash Point: 187.5°C
• Density: 1.387g/cm³
• Vapor Pressure: 5.16E-06mmHg at 25°C
• Refractive Index: 1.631
• CAS DataBase Reference: phenyl(2H-tetrazol-5-yl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl(2H-tetrazol-5-yl)methanone(14506-41-3)
• EPA Substance Registry System: phenyl(2H-tetrazol-5-yl)methanone(14506-41-3)

Safety Data

• Hazardous Substances Data: 14506-41-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Phenyl(2H-tetrazol-5-yl)methanone is used as a pharmaceutical intermediate for its potential to contribute to the development of new drugs. Its unique structure and ability to form stable complexes with metal ions make it a promising candidate for the synthesis of compounds with therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, phenyl(2H-tetrazol-5-yl)methanone is used as a key building block for the creation of more complex molecules. Its reactivity and structural features facilitate the synthesis of a variety of organic compounds, which can be further utilized in various chemical processes.
Used in Coordination Chemistry:
Phenyl(2H-tetrazol-5-yl)methanone is employed as a ligand in coordination chemistry, where it forms stable complexes with metal ions. These complexes are of interest for their potential applications in catalysis, as well as for their unique electronic and structural properties.
Used in Antimicrobial Applications:
The tetrazole moiety in phenyl(2H-tetrazol-5-yl)methanone has been studied for its antimicrobial properties, making it a potential candidate for use as an antimicrobial agent in various applications, such as in the development of new antibiotics or as a component in disinfectants.
Used in Antitumor Applications:
The potential antitumor properties of phenyl(2H-tetrazol-5-yl)methanone's tetrazole component have been investigated, suggesting that it could be used in the development of antitumor drugs, contributing to the fight against cancer.

Upstream product

• 40060-76-2 (±)-phenyl(1H-tetrazol-5-yl)methanol 
• 721-04-0 2-phenoxy-1-phenylethanone 
• 119718-87-5 cyano(phenyl)methyl acetate 
• 1202945-76-3 but-3-yn-1-yl (6-(((((1-methyl-1H-tetrazol-5-yl)(phenyl)methylene)amino)oxy)methyl)pyridin-2-yl)carbamate 
• 33452-25-4 (1?methyl?1H?tetrazol?5?yl)(phenyl)methanone 
• 6919-61-5 N-methoxy-N-methylbenzamide 
• 613-90-1 benzoyl cyanide 

Downstream Products

• 18489-25-3 5-benzyl-1H-tetrazole 
• 63920-70-7 1H-tetrazole-5-carboxylic acid anilide 
• 43134-03-8 diphenyl(1H-tetrazol-5-yl)methanol 
• 132778-86-0 1,2-diphenyl-1,2-bis-(1H-tetrazol-5-yl)-ethane-1,2-diol 
• 95898-94-5 phenyl-(5-tetrazolyl)methanamine acetate 
• 84456-99-5 phenyl[5-(p-tolyl)-1,3,4-oxadiazol-2-yl]methanone 
• 19836-23-8 phenyl(5-phenyl-1,3,4-oxadiazol-2-yl)methanone 
• 95899-18-6 C₁₁H₁₂N₈ 
• 95899-13-1 C₁₁H₁₁N₇S 
• 95899-19-7 C₁₂H₁₄N₈ 

Relevant articles and documents

Functionalization of 1 N-Protected Tetrazoles by Deprotonation with the Turbo Grignard Reagent

1N-PMB-protected tetrazole undergoes C-H deprotonation with the turbo Grignard reagent, providing a metalated intermediate with increased stability. This can be used for the reaction with electrophiles such as aldehydes, ketones, Weinreb amides, and iodine. C-H deprotonation with the turbo Grignard reagent is compatible with the PMB-protecting group at the tetrazole, which can be cleaved using oxidative hydrogenolysis and acidic conditions. The method enables the tetrazole functionalization at the fifth position by overcoming the difficulties associated with retro [2 + 3] cycloaddition of the metalated intermediates.

Phototransformation of tetrazoline oxime ethers: Photoisomerization vs. photodegradation

Fungicides showing potent biological activity in green house may have poor activity in the field due to fast photodegradation. This is the case of tetrazoline oxime ethers 1 and 2, active in the Z form, on which very little is known. A comprehensive study was therefore conducted to understand the photochemical behaviour of these compounds. It could be firmly demonstrated that both photoisomerization Z → E and photodegradation occur, and that interestingly photodegradation only takes place from E forms. Quantum yields of photoisomerization lay within the range 0.38-0.48 and those of E photodegradation in the range 0.06-0.11. During the reaction, the non-fungicidal E forms become the major isomers due to their lower solar light absorptivity than Z forms. The analytical study showed that photodegradation involves the cleavage of the N-O bond and allowed the identification of photoproducts arising from the rearrangement of the iminyl and alkoxyl radicals. Moreover, the proposed mechanism of alkoxyl radical oxidation into corresponding aldehyde and acid was elucidated using a computational study. This fundamental investigation fully explains the fast loss of the fungicidal activity of tetrazoline oxime ethers 1 and 2 in the field.

Safe and fast tetrazole formation in ionic liquids

The [2+3] cycloaddition of nitriles and azides is reliable for intramolecular reactions, but the hazards with volatile azides in intermolecular reactions are tremendous. Zinc catalysis in aqueous solution is a magnificent improvement, but requires the removal of the zinc salts from the acidic product. Herein, we report safe solvents featuring low vapor pressure and good solubility of NaN3. Ionic liquids based on alkylated imidazoles combined with microwave heating turned out to be a solution for the given tasks.