16687-60-8

Basic information

• Product Name: 5-(4-NITRO-PHENYL)-2H-TETRAZOLE
• Synonyms: BUTTPARK 2\01-81;5-(4-NITROPHENYL)TETRAZOLE;5-(4-NITRO-PHENYL)-2H-TETRAZOLE;5-(4-NITROPHENYL)-1H-TETRAZOLE;5-(4-nitrophenyl)-2H-1,2,3,4-tetrazole;4-(1H-Tetrazol-5-yl)nitrobenzene
• CAS NO: 16687-60-8
• Molecular Formula: C₇H₅N₅O₂
• Molecular Weight: 191.15
• Mol File: 16687-60-8.mol
• Article Data: 152

Chemical Properties

• Melting Point: 223°C (dec.)
• Boiling Point: 435.3 °C at 760 mmHg
• Flash Point: 217.1 °C
• Appearance: /
• Density: 1.534 g/cm³
• Vapor Pressure: 8.85E-08mmHg at 25°C
• Refractive Index: 1.662
• Storage Temp.: Store at RT.
• PKA: 3.38±0.10(Predicted)
• Water Solubility: Insoluble in water. Soluble in DMSO.
• BRN: 192840
• CAS DataBase Reference: 5-(4-NITRO-PHENYL)-2H-TETRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-NITRO-PHENYL)-2H-TETRAZOLE(16687-60-8)
• EPA Substance Registry System: 5-(4-NITRO-PHENYL)-2H-TETRAZOLE(16687-60-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 16687-60-8(Hazardous Substances Data)

Usage

Uses

It is used as a reagent used as activator for both solution- and solid-phase synthesis of oligonucleotides using the phosphoramidite method.

InChI:InChI=1/C7H5N5O2/c13-12(14)6-3-1-5(2-4-6)7-8-10-11-9-7/h1-4H,(H,8,9,10,11)

Upstream product

• 619-72-7 4-nitrobenzonitrile 
• 24067-17-2 4-nitrophenylboronic acid 
• 67-68-5 dimethyl sulfoxide 
• 619-73-8 4-nitrobenzyl chloride 
• 1129-37-9 4-nitrobenzaldehyde oxime 
• 1129-37-9 4-nitrobenzaldehyde oxime 
• 26060-30-0 4-nitrothiobenzamide 
• 555-16-8 4-nitrobenzaldehdye 
• 207301-19-7 1-(4-nitrophenyl)-4-ferrocenylmethylenetetrazolium fluoroborate 
• 207301-29-9 (O₂NC₆H₄)CN₄H(CH(CH₃)(C₅H₄)Fe(C₅H₅))⁽¹⁺⁾*BF₄^(1-)=[O₂NC₆H₄CN₄H(CH(CH₃)(C₅H₄)Fe(C₅H₅))]BF₄ 
• 636-98-6 p-nitrobenzene iodide 
• 586-78-7 para-nitrophenyl bromide 
• 619-80-7 4-nitrobenzamide 
• 81945-84-8 N-amino-4-nitrobenzene-1-carboximidamide 

Downstream Products

• 161001-97-4 phenyl 5-(4-nitrophenyl)-2H-tetrazole-2-carboxylate 
• 20743-51-5 1-methyl-5-(4-nitrophenyl)-1H-tetrazole 
• 43131-48-2 4,1,20.2-methyl-5-(4-nitrophenyl)-2H-tetrazole 
• 73670-66-3 2-(4-pentenyl)-5-(p-nitrophenyl)tetrazole 
• 22815-99-2 2-methyl-5-(4-nitrophenyl)-1,3,4-oxadiazole 
• 1090-82-0 2-(4-nitrophenyl)-5-phenyl-1,3,4-oxadiazole 
• 106191-98-4 5-(4-Nitro-phenyl)-2-(2,3,3-triiodo-allyl)-2H-tetrazole 
• 92712-28-2 2-(1'-iodopropyn-3'-yl)-5-(p-nitrophenyl)tetrazole 
• 4291-13-8 2-(4-nitrophenyl)-1,3,4-oxadiazole 
• 51449-84-4 N,N-dimethyl-4-(1⁽²⁾H-tetrazol-5-yl)-aniline 

Relevant articles and documents

Tetrazoles: LI. Synthesis of 5-substituted tetrazoles under microwave activation

Reaction of nitriles with sodium azide in the presence of ZnCl2 under microwave activation (MWA) leads to the formation of 5-tetrazoles in high yields; therewith the process is 2-3 times shorter than the inactivated reaction. Nauka/Interperiodica 2007.

Efficient synthesis of 5-substituted 1H-tetrazoles catalysed by silver(I) bis(trifluoromethanesulfoyl)nimide

An efficient method is developed for the synthesis of 5-substituted 1H-tetrazoles through the [3 + 2] cycloaddition reaction of nitriles with sodium azide using silver(I) bis(trifluoromethanesulfonyl)imide (AgNTf2) as a catalyst. This procedure provides mild reaction conditions, short reaction times and high yields.

A tetrazolate-based coordination complex with novel 3D structure and catalytic property

Hydrothermal reaction of 5-(4-nitrophenyl)-2H-tetrazole [H(4-nptz)] and CuCl generates a novel complex Cu(4-nptz). In complex (1), the tetrahedral Cu(I) cations are linked by μ4-4-nptz ligands into a 4-connected 3D framework with sra topology.

Click synthesis of 5-substituted 1H-tetrazoles from aldehydes, hydroxylamine, and [bmim]N3 via one-pot, three-component reaction

An easy and efficient one-pot, three-component method for the synthesis of 5-substituted 1H-tetrazole derivatives, via the reaction of aldehydes, hydroxylamine, and [bmim]N3, is reported. Georg Thieme Verlag KG · Stuttgart · New York.

Methionine-Coated Fe3O4 Nanoparticles: An Efficient and Reusable Nanomagnetic Catalyst for the Synthesis of 5-Substituted 1H-Tetrazoles

Abstract: Methionine-coated Fe3O4 nanoparticles, a magnetically reusable and environmentally friendly heterogeneous catalyst, was synthesized. The new catalyst was characterized by FT-IR spectra, XRD, SEM, and EDX analysis and was us

Humic acid as an efficient and reusable catalyst for one pot three-component green synthesis of 5-substituted 1: H -tetrazoles in water

Humic acid is a non toxic, inexpensive, easily available high-molecular weight polymer. A simple and facile one pot three-component synthesis of 5-substituted 1H-tetrazoles from aldehydes, hydroxyamine hydrochloride and sodium azide using humic acid as an efficient catalyst in water is described. The method reported has several advantages such as high to excellent yields, easy work-up, mild reaction conditions, use of water as a green solvent, and a commercially available, nontoxic and reusable catalyst.

The mineral alum: an effective and low-cost heterogeneous catalyst for the successful synthesis of 5-substituted-1H-tetrazoles

A simple, efficient, and green procedure for the synthesis of 5-substituted-1H-tetrazoles via [3 + 2] cycloaddition reaction of nitriles with sodium azide is described. The reaction was catalyzed by natural and mesoporous alum nanoparticles (NPs) in DMSO

An efficient Cu/functionalized graphene oxide catalyst for synthesis of 5-substituted 1H-tetrazoles

The copper nanoparticles (Cu NPs) and amide functionalized graphene oxide (Cu-Amd-RGO) catalyst were prepared. This prepared catalyst (Cu-Amd-RGO) used for the synthesis of tetrazole derivatives. The catalyst (Cu-Amd-RGO) was characterized by field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FTIR), and X-ray diffraction analysis (XRD). The average particle size of Cu was found to be 7.6?nm. The Cu-Amd-RGO catalyst exhibited excellent catalytic activity and recyclability for synthesis of tetrazoles.

One pot three-component synthesis of 5-substituted 1H-tetrazole from aldehyde

A versatile, robust and efficient strategy for the synthesis of vast range of highly functionalized 5-substituted 1H-tetrazole derivatives by using one pot three-component synthesis from various aldehydes, hydroxylamine hydrochloride and sodium azide in p

Direct conversion of aldehydes to amides, tetrazoles, and triazines in aqueous media by one-pot tandem reactions

A variety of aldehydes reacted with iodine in ammonia water at room temperature to give the nitrile intermediates, which were trapped by addition of hydrogen peroxide, sodium azide, or dicyandiamide to produce their corresponding amides, tetrazoles, and 1,3,5-triazines in modest to high yields. The one-pot tandem reactions were conducted in water media, and the products were obtained simply by extraction or filtration.

A practical multigram-scale method for the green synthesis of 5-substituted-1H-tetrazoles in deep eutectic solvent

A series of 5-substituted-1H-tetrazoles have been efficiently synthesized in moderate to excellent yields (68–90%) under mild reaction conditions by combining aryl aldehydes, hydroxylamine hydrochloride with sodium azide in the presence of catalytic amoun

Unprecedented formation of a μ-oxobridged polymeric copper(II) complex: Evaluation of catalytic activity in synthesis of 5-substituted 1H-tetrazoles

The reaction of CuCl2·2H2O with Schiff base ligand, 4-[(2-hydroxy-3-methoxybenzylidene)amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3-one] (hmdpH), in 1:1 molar ratio led to a novel and unprecedented oxo-bridged polymeric copper (II) complex, [Cu(μ-O) (hmdp)]n. The complex was isolated as crystalline solid and characterized by FTIR, UV–visible and EPR spectroscopic techniques. The molecular structure of the complex was also determined by single crystal X-ray diffraction studies. The formation of the complex is unique and unprecedented in the sense that one of the CH3 group of the 4-aminoantipyrene unit of the Schiff base ligand is oxidized in situ to CH2OH, during the complex formation. The catalytic potential of the complex has been demonstrated in the synthesis of a series of 5-substituted 1H-tetrazoles via [3 + 2]-cycloaddition reactions of substituted benzonitriles and sodium azide in ethylene glycol.

Synthesis of 5-Substituted 1H-Tetrazoles Catalyzed by M-SAPO-34 (M = Co, Cu, Mn, Fe, and V) Nanostructures

Abstract: The synthesis of 5-substituted 1H-tetrazoles by use of a series of M-SAPO-34 (M = Co, Cu, Mn, Fe, and V) nanocatalysts are presented. Following the optimized conditions, Co-SAPO-34 nanocatalyst has been found to effectively catalyze the 5-substi