365-33-3

Usage

Uses

Used in Organic Synthesis:
2-Nitrobenzenediazonium tetrafluoroborate is used as a synthetic intermediate for the preparation of various organic compounds. Its reactivity allows it to participate in a wide range of chemical reactions, such as coupling reactions, which are essential for the formation of new chemical bonds and the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Nitrobenzenediazonium tetrafluoroborate is utilized as a building block for the synthesis of active pharmaceutical ingredients (APIs). Its ability to form various chemical bonds makes it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Dye and Pigment Industry:
2-Nitrobenzenediazonium tetrafluoroborate is also employed in the dye and pigment industry for the synthesis of azo dyes and pigments. These compounds are widely used in various applications, including textiles, plastics, and printing inks, due to their vibrant colors and stability.
Used in Chemical Research:
In the field of chemical research, 2-Nitrobenzenediazonium tetrafluoroborate serves as a valuable tool for studying reaction mechanisms and exploring new synthetic pathways. Its unique reactivity allows researchers to gain insights into the behavior of diazonium salts and their potential applications in various chemical processes.

InChI:InChI=1/C6H4N3O2.B.4FH/c7-8-5-3-1-2-4-6(5)9(10)11;;;;;/h1-4H;;4*1H/q+1;+3;;;;/p-4

Upstream product

• 88-74-4 2-nitro-aniline 
• 109-63-7 boron trifluoride diethyl etherate 
• 7632-00-0 sodium nitrite 
• 13755-29-8 sodium tetrafluoroborate 
• 540-80-7 tert.-butylnitrite 

Downstream Products

• 109509-95-7 5-[3-(2-nitro-phenyl)-triazenyl]-3-phenyl-[1,2,4]thiadiazole 
• 27328-95-6 3-(2-nitro-phenylhydrazono)-2-oxo-2,3-dihydro-oxazolo[3,2-a]pyridinylium betaine 
• 61053-50-7 methyl(2-nitrophenyl)selenide 
• 132993-22-7 2-nitrophenyl trifluoromethanesulfonate 
• 84451-31-0 o-nitrotellurophenetole 
• 152770-36-0 2-acetonyl-5-nitro-5-(2-nitrophenylazo)-4,6-dimethoxy-2,5-dihydropyrimidine 
• 152770-45-1 N-methoxycarbonyl-N'-<1-acetonyl-2-nitro-2-(2-nitrophenylhydrazono)>ethyl-O-methylisourea 
• 609-73-4 o-nitroiodobenzene 
• 71129-54-9 bis(2-nitrophenyl) telluride 
• 72726-15-9 2-nitrophenyl tellurocyanate 
• 98-95-3 nitrobenzene 
• 89185-84-2 3-(2-Nitrophenyl)-2,4-pentanedione 
• 86-00-0 2-nitrobiphenyl 
• 69625-10-1 (E)-2-nitro-benzenediazo hydroxide; sodium-salt 

Relevant academic research and scientific papers

Metal-Free Visible-Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism

The first metal-free procedure for the synthesis of arylsulfonyl fluorides is reported. Under organo-photoredox conditions, aryl diazonium salts react with a readily available SO2 source (DABSO) to afford the desired product through simple nucleophilic fluorination. The reaction tolerates the presence of both electron-rich and -poor aryls and demonstrated a broad functional group tolerance. To shed the light on the reaction mechanism, several experimental techniques were combined, including fluorescence, NMR, and EPR spectroscopy as well as DFT calculations.

Matsuda-Heck arylation of itaconates: A versatile approach to heterocycles from a renewable resource

Itaconic acid esters and hemiesters undergo Pd-catalyzed coupling reactions with arene diazonium salts in high to excellent yields. The coupling products of ortho-nitro arene diazonium salts can be converted in one or two steps to benzazepine-2-ones.

Modular and Selective Arylation of Aryl Germanes (C?GeEt3) over C?Bpin, C?SiR3 and Halogens Enabled by Light-Activated Gold Catalysis

Selective C (Formula presented.) –C (Formula presented.) couplings are powerful strategies for the rapid and programmable construction of bi- or multiaryls. To this end, the next frontier of synthetic modularity will likely arise from harnessing the coupling space that is orthogonal to the powerful Pd-catalyzed coupling regime. This report details the realization of this concept and presents the fully selective arylation of aryl germanes (which are inert under Pd0/PdII catalysis) in the presence of the valuable functionalities C?BPin, C?SiMe3, C?I, C?Br, C?Cl, which in turn offer versatile opportunities for diversification. The protocol makes use of visible light activation combined with gold catalysis, which facilitates the selective coupling of C?Ge with aryl diazonium salts. Contrary to previous light-/gold-catalyzed couplings of Ar–N2+, which were specialized in Ar–N2+ scope, we present conditions to efficiently couple electron-rich, electron-poor, heterocyclic and sterically hindered aryl diazonium salts. Our computational data suggest that while electron-poor Ar–N2+ salts are readily activated by gold under blue-light irradiation, there is a competing dissociative deactivation pathway for excited electron-rich Ar–N2+, which requires an alternative photo-redox approach to enable productive couplings.

Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: Synthesis of: N -arylpyrazoles

A general method for the synthesis of structurally diverse N-arylpyrazoles from readily available cyclopropanols and aryldiazonium salts is disclosed. The reaction was conducted at room temperature within minutes with a broad substrate scope and excellent regioselectivity.

Copper(I)-promoted trifluoromethylthiolation of arenediazonium salts with AgSCF3

An efficient method for trifluoromethylthiolation of arenediazonium salts has been developed in mild conditions with a stable and convenient AgSCF3. It provides a straightforward and convenient way for the synthesis of trifluoromethylthiolated compound from diazonium salts in moderate to good yields.

Method for producing 4-fluoro-3-(trifluoromethylsulfonyl)benzenesulfonamide

The invention provides a method for producing 4-fluoro-3-(trifluoromethylsulfonyl)benzenesulfonamide. 2-nitroaniline is used as an initial raw material, is subjected to diazotization reaction, trifluoromethyl sulfonation reaction, fluoronation, chlorosulfonation reaction, and is reacted with ammonium hydroxide to finally produce the 4-fluoro-3-(trifluoromethylsulfonyl)benzenesulfonamide. Comparedwith reported synthesis methods, the method for producing the 4-fluoro-3-(trifluoromethylsulfonyl)benzenesulfonamide has the advantages that the reaction yield of the synthesis route is high, used reaction agents are economic and easy to obtain, reaction conditions are mild and controllable, and in a reaction process, column chromatography and purification are not needed, so that the method for producing the 4-fluoro-3-(trifluoromethylsulfonyl)benzenesulfonamide has wide commercial application prospects.

Ferrocene catalysed C–H arylation of arenes and reaction mechanism study using cyclic voltammetry

Ferrocene catalysed C–H arylation of benzene using aryldiazonium salt is studied. Yield of biphenyl in this reaction was found to be better than some of the known methods. Aryldiazonium salts with electron withdrawing groups produced excellent yields (upto 85%) in C–H arylation. Applicability of this reaction was studied on several arenes and heteroarene such as benzene, naphthalene, anthracene, pyrene and pyridine. Catalytic role of ferrocene in aryl radical formation was studied by cyclic voltammetry of phenyldiazonium tetrafluoroborate. In presence of ferrocene more radical formation was observed. This reaction model works at ambient temperature and features the use of inexpensive catalyst for the synthesis of biaryl derivatives.

Gold-catalysed cross-coupling between aryldiazonium salts and arylboronic acids: Probing the usefulness of photoredox conditions

The synthesis of biaryl compounds from aryldiazonium salts and arylboronic acids was achieved using PPh3AuCl as catalyst, CsF as base and acetonitrile as solvent. Combined to photosensitizers, irradiation by blue LEDs allowed accelerating the reaction and expanding its scope. Various functional groups were compatible including bromoaryls, iodoaryls, aldehydes and alcohols. A 2-iodobenzyl alcohol moiety was smoothly introduced by this method, enabling its consecutive isotopic labelling by a Pd-catalysed alkoxycarbonylation.

An unprecedentedly simple method of synthesis of aryl azides and 3-hydroxytriazenes

Fischer's approach towards the synthesis of aryl azides and triazinoles from diazonium salts and hydroxylammonium chloride (phenylhydraxylamine) was reinvestigated and optimized. The new methodology enables the preparation of aryl azides and triazinoles in high yields in water at room temperature. The procedure is very simple, robust, easily scalable, reproducible, and "green".

Palladium(II)-catalyzed intramolecular tandem aminoalkylation via divergent C(sp3)-H functionalization

(Chemical Equation Presented) We have developed a Pd(II)-catalyzed oxidative tandem aminoalkylation via divergent C(sp3)-H functionalization, a ffording three- and five-membered-ring fused indolines in good yields under two optimized conditions, respectively. The mechanism studies have indicated that the benzylic C - H cleavage involved in the former transformation is the rate-determining step, while the cleavage of amide α-C - H in the latter is not. This is the first example of a Pd-catalyzed tandem reaction involving C(sp3)-H activation without the employment of prefunctionalized reagents (e.g., halogenated and boron reagents) and directing groups, representing a green and economic protocol for the construction of N-containing heterocycles.