14064-61-0

Basic information

• Product Name: 5-(4-CHLORO-BENZYL)-2H-TETRAZOLE
• Synonyms: 5-(4-CHLOROBENZYL)-2H-1,2,3,4-TETRAAZOLE;5-(4-CHLORO-BENZYL)-2H-TETRAZOLE;AKOS B020753;BUTTPARK 84\02-04;ART-CHEM-BB B020753;5-(4-Chlorobenzyl)tetrazole;5-(4-chlorobenzyl)-1H-tetrazole(SALTDATA: FREE);5-(4-chlorobenzyl)-2H-tetraazole
• CAS NO: 14064-61-0
• Molecular Formula: C₈H₇ClN₄
• Molecular Weight: 194.62
• Mol File: 14064-61-0.mol

Chemical Properties

• Melting Point: 164 °C
• Boiling Point: 387°Cat760mmHg
• Flash Point: 219.9°C
• Appearance: /
• Density: 1.402g/cm³
• Vapor Pressure: 3.4E-06mmHg at 25°C
• Refractive Index: 1.626
• PKA: 4.69±0.10(Predicted)
• CAS DataBase Reference: 5-(4-CHLORO-BENZYL)-2H-TETRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-CHLORO-BENZYL)-2H-TETRAZOLE(14064-61-0)
• EPA Substance Registry System: 5-(4-CHLORO-BENZYL)-2H-TETRAZOLE(14064-61-0)

Safety Data

• Hazardous Substances Data: 14064-61-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
5-(4-Chloro-benzyl)-2H-tetrazole is used as a building block for synthesizing more complex molecules. Its unique structure allows for various chemical reactions, making it a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds.
Used in Photoelectric Applications:
5-(4-Chloro-benzyl)-2H-tetrazole is used as a component in materials with photoelectric properties. Its potential use in telescopes and other optical devices highlights its importance in the development of advanced technologies that rely on light-sensitive materials.
Used in Research and Development:
5-(4-Chloro-benzyl)-2H-tetrazole is used as a research compound for studying the properties and reactions of tetrazoles. Its unique structure provides insights into the behavior of nitrogen-rich compounds and their potential applications in various fields, including materials science and pharmaceuticals.

InChI:InChI=1/C8H7ClN4/c9-7-3-1-6(2-4-7)5-8-10-12-13-11-8/h1-4H,5H2,(H,10,11,12,13)

Upstream product

• 1878-66-6 4-chlorophenylacetic Acid 
• 20101-92-2 2-(4-chlorophenyl)acetamide 
• 140-53-4 p-chlorobenzyl cyanide 

Downstream Products

• 950272-35-2 2-(4-chlorobenzyl)-5-phenyl-1,3,4-oxadiazole 
• 1230658-90-8 5-(4-chlorobenzyl)-2-(4-nitrophenyl)tetrazole 
• 1230658-84-0 5-(4-chlorobenzyl)-1-(4-nitrophenyl)tetrazole 

Relevant articles and documents

Aluminum(III) hydrogensulfate: An efficient solid acid catalyst for the preparation of 5-substituted 1H-tetrazoles

An efficient method for preparation of 5-substituted 1H-tetrazoles via [2+3] cycloaddition of nitriles and sodium azide is reported using aluminum(III) hydrogensulfate as an effective solid acid. This method has the advantages of good yields, simple methodology, and easy workup. Copyright

Highly efficient synthesis of 1- and 5-substituted 1H-tetrazoles using chitosan derived magnetic ionic liquid as a recyclable biopolymer-supported catalyst

A general method for the efficient synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines is described using chitosan supported magnetic ionic liquid nanoparticles (CSMIL) as a novel heterogeneous catalyst. The application of this catalyst allows the synthesis of a variety of tetrazoles in high yields at low temperature. This new magnetic catalyst has been prepared from chitosan (the most abundant biopolymer in nature and cheap industrial waste) and methyl imidazole (a widely available backbone of ionic liquids) which was reacted with FeCl3 to obtain the CS-EMImFeCl4 catalyst. This methodology illustrates a very simple procedure, with wide applicability, environmental friendliness and reusability of catalyst. The new catalyst was characterized using some different microscopic and spectroscopic techniques such as transmission electron microscopy (TEM), scanning electron microscopy (SEM), FTIR spectroscopy, and Raman spectroscopy. The novel catalyst has therefore a great potential to be used in green processes. The Royal Society of Chemistry 2013.

The microwave-assisted synthesis of 5-substituted 1: H -tetrazoles via [3+2] cycloaddition over a heterogeneous Cu-based catalyst: Application to the preparation of 13N-labelled tetrazoles

The [3+2] cycloaddition between various nitriles and sodium azide proceeds smoothly in the presence of a new CuII catalyst in N-methyl-2-pyrrolidone (NMP) to give the corresponding 5-substituted 1H-tetrazoles. The desired tetrazoles were obtain

FeCl3-SiO2 as a reusable heterogeneous catalyst for the synthesis of 5-substituted 1H-tetrazoles via [2+3] cycloaddition of nitriles and sodium azide

An efficient method for the preparation of 5-substituted 1H-tetrazole derivatives is reported using FeCl3-SiO2 as an effective heterogeneous catalyst. This method has the advantages of high yields, simple methodology, and easy work-up. The catalyst can be recovered by simple filtration and reused delivering good yields.

Amberlyst-15 catalyzed synthesis of 5-substituted 1-H-tetrazole via [3+2] cycloaddition of nitriles and sodium azide

A mild and efficient method for the preparation of 5-substituted 1-H-tetrazole derivatives is reported using solid acidic resin Amberlyst-15 as an effective heterogeneous catalyst. This method is advantageous because of non-toxicity and stability of catalyst, high product yield, simple methodology, and easy work up. The catalyst was recovered by simple filtration and reused several times delivering moderate to good product yield.

Nanocrystalline ZnO as an efficient heterogeneous catalyst for the synthesis of 5-substituted 1H-tetrazoles

Nanocrystalline ZnO is an effective heterogeneous catalyst for the [2 + 3]-cycloaddition of sodium azide with nitriles to afford 5-substituted 1H-tetrazoles in good yields.

An experimental and computational assessment of acid-catalyzed azide-nitrile cycloadditions

The mechanism of the azidea-nitrile cycloaddition mediated by different Bronsted and Lewis acids has been addressed through DFT calculations. In all cases activation of the nitrile substrate by the Bronsted or Lewis acid catalyst was found to be responsib

Lithiation Substitution of Unprotected Benzyltetrazoles

1H-Tetrazoles occupy an important role in modern medicinal chemistry, but few methods for their modification exist. Many extant protocols require the use of a difficult to remove N-alkyl-protecting group, precluding the products from use as carboxylate bioisosteres, the major role of tetrazoles in pharmaceuticals. We herein report a convenient, protecting-group-free lithiation-substitution protocol for benzylic tetrazoles. Metalation with n-BuLi at 0 °C followed by electrophilic trapping gave a range of α-functionalized benzyltetrazoles in up to 91% yield.

Synthesis, molecular docking and xanthine oxidase inhibitory activity of 5-aryl-1H-tetrazoles

5-Aryl-1H-tetrazoles (1–24) were synthesized and screened for their xanthine oxidase (XO) inhibitory activity using allopurinol as standard inhibitor (IC50 = 2.0 ± 0.01 μM). Six compounds 3, 4, 5, 9, 21, and 24 exhibited significant to weak act

L -Proline: An Efficient Organocatalyst for the Synthesis of 5-Substituted 1 H -Tetrazoles via [3+2] Cycloaddition of Nitriles and Sodium Azide

A simple and efficient route for the synthesis of a series of 5-substituted 1 H -tetrazoles using l -proline as a catalyst from structurally diverse organic nitriles and sodium azide is reported. The prominent features of this environmentally benign, cost effective, and high-yielding l -proline-catalyzed protocol includes simple experimental procedure, short reaction time, simple workup, and excellent yields making it a safer and economical alternative to hazardous Lewis acid catalyzed methods. The protocol was successfully applied to a broad range of substrates, including aliphatic and aryl nitriles, organic thiocyanates, and cyanamides.