24067-17-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Nitrophenylboronic acid is used as a synthetic intermediate for the preparation of combretastatin analogs, which are potential antitumor agents. It is also used in the synthesis of human immunodeficiency virus (HIV) protease inhibitors with antiviral activities against drug-resistant viruses.
Used in Chemical Synthesis:
4-Nitrophenylboronic acid is used as a reagent for ligand-free palladium-catalyzed Suzuki-Miyaura cross-couplings, which are essential in the formation of carbon-carbon bonds in organic synthesis. It is also used in ruthenium-catalyzed direct arylation of benzylic sp3 carbons of acyclic amines, Diels-Alder or C-H activation reactions, and regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulations.
Used in Environmentally Benign Synthesis:
4-Nitrophenylboronic acid is used in an environmentally benign one-pot synthesis through a double arylation process, which reduces waste and improves efficiency in chemical synthesis.
Used in Copper-Mediated Reactions:
It is used as a reagent in copper-mediated cyanations and copper-catalyzed arylations, which are important for the synthesis of various organic compounds.
Used in Regioselective Glycosylations:
4-Nitrophenylboronic acid is used in regioselective glycosylations, which are crucial for the synthesis of complex carbohydrates and their derivatives.
Used in Suzuki Couplings:
It is used in Suzuki couplings followed by arylations, which are essential for the formation of biaryl compounds and have applications in the synthesis of pharmaceuticals, agrochemicals, and materials.
Used in X-ray Absorption:
4-Nitrophenylboronic acid is used as a reagent on rhodium-grafted hydrotalcite catalyst for heterogeneous 1,4-addition reaction of organoboron reagents to electron-deficient olefins, which is important for the development of new catalytic systems and synthetic methods.
Used in Suzuki Reaction:
4-Nitrophenylboronic acid is used in the Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds in organic synthesis, particularly useful for the synthesis of complex molecules and biologically active compounds.

InChI:InChI=1/C6H6BNO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4,9-10H

Upstream product

• 108-24-7 acetic anhydride 
• 98-80-6 phenylboronic acid 
• 850693-33-3 C₆H₄BF₃NO₂^(1-) 
• 636-98-6 p-nitrobenzene iodide 
• 73183-34-3 bis(pinacol)diborane 
• 100-00-5 4-chlorobenzonitrile 
• 586-78-7 para-nitrophenyl bromide 
• 13675-18-8 tetrahydroxydiboron 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 100-01-6 4-nitro-aniline 
• 55124-35-1 diisopropylamine borane 
• 7732-18-5 water 
• 67-56-1 methanol 

Downstream Products

• 89415-43-0 (4-aminophenyl)boronic acid 
• 52099-42-0 2-(4-nitro-phenyl)-[1,3,6,2]dioxazaborocane 
• 120185-88-8 3-(4-nitrophenyl)-4H-1-benzopyran-4-one 
• 5747-27-3 2-(4-nitro-phenyl)-benzo[1,3,2]dioxaborole 
• 233770-26-8 2-formyl-3-(p-nitrophenyl)-1-tosylpyrrole 
• 417699-11-7 2,2-dimethoxy-5-(4-nitrophenyl)indan-1,3-dione 
• 355399-68-7 [7-Chloro-6-(4-nitrophenyl)-2-oxo-1,2-dihydro-3-quinolyl]-phosphonic acid diethyl ester 
• 7147-77-5 5-(4-nitrophenyl)-2-furaldehyde 
• 101-63-3 bis(4-nitrophenyl)ether 
• 52939-00-1 5-(4-nitrophenyl)furan-2-carboxylic acid methyl ester 
• 6242-98-4 4'-bromo-4-nitrobiphenyl 
• 3282-11-9 p,p-dinitro-p-terphenyl 

Relevant academic research and scientific papers

Microwave-assisted transition-metal-catalyzed synthesis of N-shifted and ring-expanded buflavine analogues

Two novel and efficient strategies for the synthesis of hitherto unknown N-shifted and ring-expanded buflavine analogues are presented. Construction of the medium-sized ring system of the title molecules, a difficult task due to the high activation energy needed for the ring-closure with the additional rigidity imposed by the biaryl skeleton, was achieved by using Suzuki-Miyaura biaryl coupling and a ring-closing metathesis reaction as the key steps. The combination of a second-generation Grubbs catalyst and microwave irradiation proved to be highly useful in generating the otherwise difficult to obtain medium-sized ring system of the buflavine analogues.

Alkylative Dearomatization by Using an Unactivated Aryl Nitro Group as a Leaving Group: Access to Diversified Alkylated Spiro[5.5]trienones

The cleavage of an unactivated aryl nitro group triggered by alkyl radicals enables a dearomative cyclization, affording diversified alkylated spiro[5.5]trienones in good yields. Using readily available compounds (toluene and analogues, alkanes, ethers, ketones, etc.) as alkylating reagents, various alkyls have been implanted into the spirocycles via C(sp3)-H and Ar-NO2 bond activation with high functional group tolerance. This protocol provides a distinct method for the activation of the aryl nitro group.

Synthesis, structure, and synthetic potential of arenediazonium trifluoromethanesulfonates as stable and safe diazonium salts

Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2+ TfO– can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.

Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids

Owing to the unusual reactivity of dialkylamine-borane complexes, a methodology was developed to simply access boronic acids. The intrinsic instability of magnesium aminoborohydride was tweaked into a tandem dehydrogenation borylation sequence. Proceeding via an autocatalytic cycle, amineborane dehydrogenation was induced by a variety of Grignard reagents. Overall, addition of the organomagnesium species onto specially designed dialkylamine-borane complexes led to a variety of boronic acids in high yields. In addition, the reaction can be performed under Barbier conditions, on a large scale.

Development of a Concise Multikilogram Synthesis of LPA-1 Antagonist BMS-986020 via a Tandem Borylation-Suzuki Procedure

The process development for the synthesis of BMS-986020 (1) via a palladium catalyzed tandem borylation/Suzuki reaction is described. Evaluation of conditions culminated in an efficient borylation procedure using tetrahydroxydiboron followed by a tandem Suzuki reaction employing the same commercially available palladium catalyst for both steps. This methodology addressed shortcomings of early synthetic routes and was ultimately used for the multikilogram scale synthesis of the active pharmaceutical ingredient 1. Further evaluation of the borylation reaction showed useful reactivity with a range of substituted aryl bromides and iodides as coupling partners. These findings represent a practical, efficient, mild, and scalable method for borylation.

Borinic Acids via Direct Arylation of Amine-Borane Complexes: An Air- and Water-Stable Boron Source

A synthesis of borinic acids and borinates was optimized using amine-borane complexes as a water and air insensitive borylating agent. The reaction operates under convenient conditions using a non-cryogenic temperature and with no flash chromatography, and it gives no boron impurities. The reaction proceeds through a tandem dehydrogenation-double addition mechanism.

Methanol-promoted borylation of arylamines: A simple and green synthetic method to arylboronic acids and arylboronates

A Sandmeyer borylation of arylamines via a SN2Ar pathway promoted by methanol with sodium nitrite and hydrochloric acid as diazotization agent has been developed, which provide a simple and green synthetic method to arylboronic acids and arylboronates. Georg Thieme Verlag Stuttgart New York.

An easy route to (hetero)arylboronic acids

An unprecedented spontaneous reactivity between diazonium salts and diboronic acid has been unveiled, leading to a versatile arylboronic acid synthesis directly from (hetero)arylamines. This fast reaction (35 min overall) tolerates a wide range of functional groups and is carried out under very mild conditions. The radical nature of the reaction mechanism has been investigated.

Sequential one-pot access to molecular diversity through aniline aqueous borylation

On the basis of our recently reported aniline aqueous borylation, molecular diversity was achieved in a one-pot process by combining other reactions such as esterification, Suzuki-Miyaura coupling, hydrogenolysis, or Petasis borono-Mannich.

Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid

The Suzuki-Miyaura reaction has become one of the more useful tools for synthetic organic chemists. Until recently, there did not exist a direct way to make the most important component in the coupling reaction, namely the boronic acid. Current methods to make boronic acids often employ harsh or wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthesis is unveiled, which includes a wide array of synthetically useful aryl electrophiles. It makes use of the newly available second generation Buchwald XPhos preformed palladium catalyst and bis-boronic acid. For ease of isolation and to preserve the often sensitive C-B bond, all boronic acids were readily converted to their more stable trifluoroborate counterparts.