459-64-3

Usage

Uses

Used in Organic Synthesis:
4-Methoxybenzenediazonium tetrafluoroborate is used as a reagent for the preparation of azo coupled cyclic β-enaminones. This application is particularly useful in the synthesis of complex organic molecules and the development of new chemical compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Methoxybenzenediazonium tetrafluoroborate is used as a key intermediate in the synthesis of various drug molecules. Its ability to form diazonium salts allows for the creation of a wide range of pharmaceutical compounds with potential therapeutic applications.
Used in Dye and Pigment Industry:
4-Methoxybenzenediazonium tetrafluoroborate is also used in the dye and pigment industry for the production of azo dyes. These dyes are widely used in various applications, including textiles, plastics, and printing inks, due to their vibrant colors and stability.
Overall, 4-Methoxybenzenediazonium tetrafluoroborate is a versatile reagent with applications in various industries, including organic synthesis, pharmaceuticals, and dyes and pigments. Its ability to form diazonium salts makes it a valuable component in the development of new chemical compounds and products.

InChI:InChI=1/C7H7N2O.B.4FH/c1-10-7-4-2-6(9-8)3-5-7;;;;;/h2-5H,1H3;;4*1H/q+1;+3;;;;/p-4

Upstream product

• 104-94-9 4-methoxy-aniline 
• 74317-32-1 18-crown-6/p-methoxybenzenediazonium tetrafluoroborate complex 
• 5329-14-6 aminosulfonic acid 
• 51-66-1 4-methoxyacetanilide 
• 7664-39-3 hydrogen fluoride 
• 11113-50-1 boric acid 
• 13755-29-8 sodium tetrafluoroborate 
• 7632-00-0 sodium nitrite 
• 67-56-1 methanol 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 109-63-7 boron trifluoride diethyl etherate 
• 540-80-7 tert.-butylnitrite 
• 90-04-0 2-methoxy-phenylamine 
• 462-34-0 boron trifluoride-tetrahydrofuran complex 

Downstream Products

• 459-60-9 1-fluoro-4-methoxybenzene 
• 66716-02-7 2,3-bis-(4-methoxy-phenyl)-3,5,6,7-tetrahydro-2H-2aλ⁴-thia-1,2,3,4-tetraaza-cyclopenta[cd]indene 
• 69065-70-9 N',N'''-bis-(4-methoxy-phenyl)-N,N''-(4-tert-butyl-1-methoxy-1-phenyl-1λ⁵-phosphinine-2,6-diyl)-bis-diazene 
• 34658-01-0 6,7-dimethyl-benzo[4,5]imidazo[2,1-b]thiazole-2,3-dione 2-[(4-methoxy-phenyl)-hydrazone] 
• 51459-97-3 4-[3-(4-methoxy-phenylazo)-5-phenyl-furan-2-yl]-morpholine 
• 66716-04-9 2-(4-methoxy-phenyl)-3-phenyl-3,5,6,7-tetrahydro-2H-2aλ⁴-thia-1,2,3,4-tetraaza-cyclopenta[cd]indene 
• 203110-98-9 C₉H₁₃N₂O₄P 
• 18316-83-1 5,6-diphenyl-imidazo[2,1-b]thiazole-2,3-dione 2-[(4-methoxy-phenyl)-hydrazone] 
• 51208-27-6 (1,1-dimethoxy-2,6-diphenyl-1λ⁵-phosphinin-4-yl)-(4-methoxy-phenyl)-diazene 
• 37735-07-2 naphtho[1',2':4,5]imidazo[2,1-b]thiazole-8,9-dione 9-[(4-methoxy-phenyl)-hydrazone] 
• 150-78-7 1,4-dimethoxybezene 
• 86298-05-7 2-(4-Methoxy-phenyl)-4-(4-methoxy-phenylsulfanyl)-5,6-dihydro-2H-2aλ⁴,3-dithia-1,2-diaza-cyclopenta[cd]pentalene 
• 86298-10-4 2-(4-Methoxy-phenyl)-4-(4-methoxy-phenylsulfanyl)-2,5,6,7-tetrahydro-2aλ⁴,3-dithia-1,2-diaza-cyclopenta[cd]indene 
• 24845-40-7 2-(4-methoxyphenyl)acetophenone 

Relevant academic research and scientific papers

Mono- and Ditopic Bisfunctionalization of Graphene

For the first time, the bisfunctionalization of graphene by employing two successive reduction and covalent bond forming steps is reported. Bulk functionalization in dispersion and functionalization of individual sheets deposited on surfaces have both been carried out. Whereas in the former case attacks from both sides of the basal plane are possible and can lead to strain-free architectures, in the latter case, retrofunctionalizations can become important when the corresponding anion of the addend is a sufficiently good leaving group.

Deprotection of arenediazonium tetrafluoroborate ethers with BBr 3

(Chemical Equation Presented) Ether cleavage was carried out on arene bearing a diazonium salt. The deprotection takes place with boron tribromide under very mild conditions in good yields without affecting the diazonium group.

Aryl Radical Activation of C-O Bonds: Copper-Catalyzed Deoxygenative Difluoromethylation of Alcohols

Given their ubiquity in natural products and pharmaceuticals, alcohols represent one of the most attractive starting materials for the construction of C-C bonds. We report herein the first catalytic strategy to harness the reactivity of aryl radicals for the activation of C-O bonds in alcohol-derived xanthate esters, allowing for the discovery of the first catalytic deoxygenative difluoromethylation reaction. Under copper-catalyzed conditions, a wide variety of alkyl xanthate esters, readily synthesized from alcohol feedstocks, were activated by catalytically generated aryl radicals and were converted to the alkyl-difluoromethane products via alkyl radical intermediates. This scalable protocol exhibits a broad substrate scope and functional group tolerance, enabling late-stage modification of complex pharmaceutical agents. A one-pot protocol has been developed that allows for the direct use of free alcohols without purification of the xanthate esters. Mechanistic studies are consistent with the hypothesis of aryl radicals being formed and initiating the cleavage of the C-O bonds of xanthate esters, to generate alkyl radicals as the key intermediates. This aryl radical activation approach represents a new strategy for the activation of alcohols as cross-coupling partners.

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.

Aryl Diazonium Salts: Powerful Arylating Agents for Catellani-Typeortho-Arylation

The Catellani reaction provides an efficient synthetic approach to polyfunctionalized arenes. However, the selectiveortho-arylating reagents employed in these reactions have been strictly limited to activated bromoarenes. As demonstrated in this work, aryl diazonium salts bearing both electron-donating and electron-withdrawing substituents, after in situ transformations with KI into the corresponding iodoarenes, were efficient arylating reagents for Catellani typeortho-arylation approaches.

Chemical and Genetic Studies on the Formation of Pyrrolones During the Biosynthesis of Cytochalasans

A key step during the biosynthesis of cytochalasans is a proposed Knoevenagel condensation to form the pyrrolone core, enabling the subsequent 4+2 cycloaddition reaction that results in the characteristic octahydroisoindolone motif of all cytochalasans. In this work, we investigate the role of the highly conserved α,β-hydrolase enzymes PyiE and ORFZ during the biosynthesis of pyrichalasin H and the ACE1 metabolite, respectively, using gene knockout and complementation techniques. Using synthetic aldehyde models we demonstrate that the Knoevenagel condensation proceeds spontaneously but results in the 1,3-dihydro-2H-pyrrol-2-one tautomer, rather than the required 1,5-dihydro-2H-pyrrol-2-one tautomer. Taken together our results suggest that the α,β-hydrolase enzymes are essential for first ring cyclisation, but the precise nature of the intermediates remains to be determined.

Aqueous and Visible-Light-Promoted C-H (Hetero)arylation of Uracil Derivatives with Diazoniums

Direct C5 (hetero)arylation of uracil and uridine substrates with (hetero)aryl diazonium salts under photoredox catalysis with blue light was reported. The coupling proceeds efficiently with diazonium salts and heterocycles in good functional group tolerance at room temperature in aqueous solution without transition-metal components. A plausible radical mechanism has been proposed.

Light- and Manganese-Initiated Borylation of Aryl Diazonium Salts: Mechanistic Insight on the Ultrafast Time-Scale Revealed by Time-Resolved Spectroscopic Analysis

Manganese-mediated borylation of aryl/heteroaryl diazonium salts emerges as a general and versatile synthetic methodology for the synthesis of the corresponding boronate esters. The reaction proved an ideal testing ground for delineating the Mn species responsible for the photochemical reaction processes, that is, involving either Mn radical or Mn cationic species, which is dependent on the presence of a suitably strong oxidant. Our findings are important for a plethora of processes employing Mn-containing carbonyl species as initiators and/or catalysts, which have considerable potential in synthetic applications.

Azoacetylenes for the Synthesis of Arylazotriazole Photoswitches

We report a modular approach toward novel arylazotriazole photoswitches and their photophysical characterization. Addition of lithiated TIPS-acetylene to aryldiazonium tetrafluoroborate salts gives a wide range of azoacetylenes, constituting an underexplored class of stable intermediates.In situdesilylation transiently leads to terminal arylazoacetylenes that undergo copper-catalyzed cycloadditions (CuAAC) with a diverse collection of organoazides. These include complex molecules derived from natural products or drugs, such as colchicine, taxol, tamiflu, and arachidonic acid. The arylazotriazoles display near-quantitative photoisomerization and long thermalZ-half-lives. Using the method, we introduce for the first time the design and synthesis of a diacetylene platform. It permits implementation of consecutive and diversity-oriented approaches linking two different conjugants to independently addressable acetylenes within a common photoswitchable azotriazole. This is showcased in the synthesis of several photoswitchable conjugates, with potential applications as photoPROTACs and biotin conjugates.

Palladium-Catalyzed Formal (3 + 2) Cycloaddition Reactions of 2-Nitro-1,3-enynes with Vinylaziridines, -epoxides, and -cyclopropanes

A two-step Pd-catalyzed (3 + 2) cycloaddition/HNO2 elimination reaction sequence has been developed to give novel cyclic 1,3-dien-5-yne systems from Pd-stabilized zwitterionic 1,3-dipoles and 2-nitro-1,3-enyne substrates. The process is highly atom-efficient and tolerates the reaction of 2-vinyloxirane, 1-tosyl-2-vinylaziridine, and diethyl 2-vinylcyclopropane-1,1-dicarboxylate derived 1,3-dipoles with a variety of 2-nitro-1,3-enyne substrates. The stereochemistry of the intermediate (3 + 2) cycloadducts was determined by single crystal X-ray analysis. Furthermore, a selective kinetic elimination of the cycloadduct with an antiperiplanar relationship between the NO2 group and the participating hydrogen was demonstrated, allowing for efficient isolation of a single diastereoisomer of the cycloadduct.