456-25-7

Usage

Uses

Used in Organic Synthesis:
4-carboxybenzediazonium tetrafluoroborate serves as a versatile reagent in organic synthesis, particularly for the preparation of azo dyes and pigments. Its unique structure allows for a range of reactions that contribute to the color and properties of these compounds.
Used in Pharmaceutical Production:
4-carboxybenzediazonium tetrafluoroborate also finds application in the pharmaceutical industry, where it is utilized in the production of various drugs. Its role as an intermediate in synthesis processes is crucial for creating the desired medicinal compounds.
Used as an Intermediate in Synthesis:
4-carboxybenzediazonium tetrafluoroborate is employed as an intermediate in the synthesis of a variety of organic compounds. Its reactivity and functional groups make it a key component in creating complex organic molecules for different applications.
Used in Chemical Research:
In the field of chemical research, 4-carboxybenzediazonium tetrafluoroborate is used to explore new reaction pathways and to understand the behavior of diazonium compounds under various conditions.

Upstream product

• 540-80-7 tert.-butylnitrite 
• 150-13-0 4-amino-benzoic acid 
• 13755-29-8 sodium tetrafluoroborate 
• 7632-00-0 sodium nitrite 

Downstream Products

• 115974-97-5 methyl (E)-4-carboxyl cinnamate 
• 1386388-88-0 4-(phenyltellanyl)benzoic acid 
• 6427-66-3 4-azidobenzoic acid 
• 456-22-4 4-Fluorobenzoic acid 
• 619-58-9 4-iodobenzoic acid 
• 138-41-0 4-(aminosulfonyl)-benzoic acid 
• 216955-64-5 4-(2H-tetrazol-2-yl)benzoic acid 
• 669713-98-8 1-tert-butoxycarbonyl-2-(4-carboxyphenyl)pyrrole 
• 29886-62-2 4-thiophen-2-yl-benzoic acid 
• 35461-98-4 4-(furan-2-yl)benzoic acid 
• 117076-42-3 4-<2-(Methoxycarbonyl)ethenyl>benzoyl-chlorid 

Relevant academic research and scientific papers

Aryl diazonium chemistry for the surface functionalization of glassy biosensors

Nanostring resonator and fiber-optics-based biosensors are of interest as they offer high sensitivity, real-time measurements and the ability to integrate with electronics. However, these devices are somewhat impaired by issues related to surface modification. Both nanostring resonators and photonic sensors employ glassy materials, which are incompatible with electrochemistry. A surface chemistry approach providing strong and stable adhesion to glassy surfaces is thus required. In this work, a diazonium salt induced aryl film grafting process is employed to modify a novel SiCN glassy material. Sandwich rabbit IgG binding assays are performed on the diazonium treated SiCN surfaces. Fluorescently labelled anti-rabbit IgG and anti-rabbit IgG conjugated gold nanoparticles were used as markers to demonstrate the absorption of anti-rabbit IgG and therefore verify the successful grafting of the aryl film. The results of the experiments support the effectiveness of diazonium chemistry for the surface functionalization of SiCN surfaces. This method is applicable to other types of glassy materials and potentially can be expanded to various nanomechanical and optical biosensors.

Preparation of water-dispersible palladium nanoparticles stabilized by carbon-palladium bonds and application to Suzuki-Miyaura coupling in water

Water-dispersible palladium nanoparticle catalysts have been prepared using palladium-carbon covalent bonds. They worked as an excellent catalyst for Suzuki-Miyaura coupling reaction in water. Even though the particle size of Pd nanoparticles was much larger than the previously reported ones, they showed a very good catalytic activity for the coupling reaction.

Method for preparing iodo-benzoic acid (ester) by improving moral Michael reaction

The invention discloses a method for preparing iodo-benzoic acid (ester) by improving a moral reaction, and belongs to the technical field of organic synthesis. The method comprises the following steps: preparing and separating the diazonium tetrafluoroborate through diazotization of aminobenzoic acid (ester) and then performing iodination reaction with the iodinated reagent in an organic medium to obtain the corresponding iodo carboxylic acid (ester). The iodo-benzoic acid (ester) prepared by the method has high purity. The method has the advantages of good quality and simple post-treatment, and the product yield reaches 70 - 90%.

Hypervalent Iodine(III)-Catalyzed Balz–Schiemann Fluorination under Mild Conditions

An unprecedented hypervalent iodine(III) catalyzed Balz–Schiemann reaction is described. In the presence of a hypervalent iodine compound, the fluorination reaction proceeds under mild conditions (25–60 °C), and features a wide substrate scope and good functional-group compatibility.

Chemoselective Rapid Azo-Coupling Reaction for Bioconjugation

Novel biomolecular conjugates containing non-natural aromatic chemical moieties covalently coupled to a diazonium compound and methods of their use are disclosed.

A Chemoselective Rapid Azo-Coupling Reaction (CRACR) for Unclickable Bioconjugation

Chemoselective modification of complex biomolecules has become a cornerstone of chemical biology. Despite the exciting developments of the past two decades, the demand for new chemoselective reactions with unique abilities, and those compatible with existing chemistries for concurrent multisite-directed labeling, remains high. Here we show that 5-hydroxyindoles exhibit remarkably high reactivity toward aromatic diazonium ions and this reaction can be used to chemoselectively label proteins. We have previously genetically encoded the noncanonical amino acid 5-hydroxytryptophan in both E. coli and eukaryotes, enabling efficient site-specific incorporation of 5-hydroxyindole into virtually any protein. The 5-hydroxytryptophan residue was shown to allow rapid, chemoselective protein modification using the azo-coupling reaction, and the utility of this bioconjugation strategy was further illustrated by generating a functional antibody-fluorophore conjugate. Although the resulting azo-linkage is otherwise stable, we show that it can be efficiently cleaved upon treatment with dithionite. Our work establishes a unique chemoselective "unclickable" bioconjugation strategy to site-specifically modify proteins expressed in both bacteria and eukaryotes.

Method and manufacturing method thereof and a metal particulate carrier org. compd.

PROBLEM TO BE SOLVED: To provide: a metal particulate carrier produced using an environmentally-friendly polar solvent, particularly a water-based solvent through a simple process; a method for production of the carrier; and a catalyst comprising the metal particulate carrier by which an objective compound can be obtained at high efficiency in the reaction of an organic compound such as, hydration, oxidation, reduction or cross coupling. SOLUTION: The metal particulate carrier is obtained through supporting by a carrier comprising an inorganic or carbon material, of a metal particulate which has a bond of phenyl skeleton and metal M represented by formula (I) (wherein X1is (CH2)nCOOH or salt thereof, or a corresponding carboxylate ion (n=0 to 3); m is an integer of 1 to 5; and M is at least one metal selected from transition metals of groups 9, 10 and 11). COPYRIGHT: (C)2012,JPOandINPIT

Azo-aromatic functionalized polyethylene by nitroxide radical coupling (NRC) reaction: Preparation and photo-physical properties

The nitroxide radical coupling (NRC) reaction between the 4-(phenylazo)-benzoyl-2,2,6,6-tetramethylpiperidine-1-oxyl radical (AzO-TEMPO) or the 4-(2-thienylazo)-benzoyl-2,2,6,6-tetramethylpiperidine-1-oxyl radical (ThiO-TEMPO) and polyethylene macroradicals allowed the preparation of "functional" polyolefins bearing covalently grafted azo-aromatic chromophores. A comparison of the photo-physical behavior of the free and grafted RO-TEMPO molecules was carried out by UV-Vis spectroscopy irradiating the free RO-TEMPO solutions and the functionalized polymer films at 366 and 254 nm. Results evidenced the transfer of the photo-physical properties of the chromophores to the polymer matrix. Interestingly, some different isomerization abilities and kinetics between the free and grafted RO-TEMPO moieties, depending on the nature of the aromatic group bonded to the diazo-moiety and on the structure of the polymer matrix, were observed. Indeed, when the chromophores were grafted to the polymer, the isomerization resulted to be less efficient in terms of photo-isomerization degree and isomerization rate than in solution, suggesting a strong effect of the semi-crystalline matrix especially in the case of the more rigid HDPE. Finally the determination of the water contact angle of the functionalized polymers, before and after photo-isomerization, confirmed the occurrence of the isomerization and evidenced an increase of the wettability of the polymer surface owing to the process.

GOLD FINE PARTICLE MATRIX METALLOPROTEASE INHIBITOR

PROBLEM TO BE SOLVED: To provide a matrix metalloprotease inhibitor in which cytotoxicity and genetic toxicity are markedly inhibited. SOLUTION: A matrix metalloprotease inhibitor according to the present invention comprises gold nanoparticles. Each of the gold nanoparticles has, on its surface, a protectant comprising a functional group capable of coordinate bonding to a zinc ion at an enzyme activation site of matrix metalloprotease. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Synthesis of 2-aryl-2H-tetrazoles via a regioselective [3+2] cycloaddition reaction

A regioselective cycloaddition reaction of arenediazonium salts with trimethylsilyldiazomethane is reported. A series of 2-aryltetrazoles were obtained in good to moderate yields with wide functional group compatibility. Furthermore, this cycloaddition reaction opens the way to build up the versatile intermediate 2-aryl-5-bromotetrazole.