280563-63-5

Usage

Uses

Used in Organic Synthesis:
3-Aminophenylboronic acid is utilized as a reagent for the formation of carbon-carbon bonds, particularly in the Suzuki-Miyaura cross-coupling reaction. Its role in this reaction is crucial for the synthesis of various organic compounds, making it a valuable component in the field of organic chemistry.
Used in Sensor Development:
Leveraging its ability to form stable complexes with diols and polyols, 3-aminophenylboronic acid is employed in the development of sensors for glucose monitoring. This application is significant for the medical and biotechnology industries, where accurate and sensitive glucose detection is essential for diabetes management.
Used in Pharmaceutical Industry:
3-Aminophenylboronic acid has demonstrated potential as a therapeutic agent in the treatment of diabetes and cancer. Its capacity to inhibit specific enzymes and receptors involved in these diseases positions it as a promising candidate for drug development, offering new avenues for treatment and disease management.

Upstream product

• 13331-27-6 m-nitrobenzene boronic acid 
• 98-80-6 phenylboronic acid 
• 585-79-5 m-nitrobromobenzene 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 1160186-73-1 potassium 3-aminophenyltrifluoroborate 
• 7732-18-5 water 
• 1020180-02-2 3-bromo-N-(diphenylmethylene)-benzenamine 
• 591-19-5 m-Bromoaniline 
• 85006-23-1 3-aminophenylboronic acid hydrochloric salt 

Downstream Products

• 100607-14-5 (3-((ethoxycarbonyl)amino)phenyl)boronic acid 
• 1449484-93-8 3-(1-(pyridin-2-yl)piperidin-2-yl)aniline 
• 1449484-54-1 cis-3,3'-(1-(pyridin-2-yl)piperidine-2,6-diyl)dianiline 
• 1371629-14-9 8-(3-aminophenyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid 

Relevant academic research and scientific papers

Potentiometric saccharide detection based on the pKa changes of poly(aniline boronic acid)

A novel approach for the potentiometric detection of saccharides using poly(aniline boronic acid) is presented. A model is described in which the electrochemical potential is sensitive to the change in the pKa of the conducting polymer as a result of boronic acid-diol complexation. In this system, boronic acid complexation is the mode of transduction and it is manifested as changes in the electrochemical potential of the polymer with remarkable selectivity. Characteristics of both transient and steady-state response associated with the complexation are discussed. The presence of Nafion and fluoride during the electrochemical polymerization of 3-aminophenylboronic acid are shown to impact the sensitivity and the stability of the electrode response. The sensor sensitivity is improved significantly by increasing the concentration of sodium fluoride during the polymerization. Finally, the nature of the selectivity of the boronic acid-diol reaction under these conditions is explored by using molecular orbital calculations.

Method for synthesizing 3-aminobenzeneboronic acid

The invention discloses a method for synthesizing 3-aminobenzeneboronic acid, and belongs to the field of organic synthesis. The method comprises the following steps: performing coupling reaction on 3-nitrobromobenzene and catechol diboron under action of a palladium catalyst; adding water for quenching; adding an acid for salifying a product and entering a water layer; adding alkali into the separated water layer to adjust to near neutral; and extracting and desolventizing to obtain the 3-aminobenzeneboronic acid. The method is simple in operation, high in purity of the obtained product and suitable for industrialized scale-up production.

NITROGENOUS HETEROCYCLIC COMPOUND, PREPARATION METHOD, INTERMEDIATE, COMPOSITION AND USE

Disclosed are a nitrogenous heterocyclic compound, intermediates, a preparation method, a composition and use thereof. The nitrogenous heterocyclic compound in the present invention is as shown in formula I. The compound has a high inhibitory activity towards ErbB2 tyrosine kinase and a relatively good inhibitory activity towards human breast cancer BT-474 and human gastric cancer cell NCI-N87 which express ErbB2 at a high level, and at the same time has a relatively weak inhibitory activity towards EGFR kinase. Namely, the compound is a highly selective small-molecule inhibitor targeted at ErbB2, and hence it has a high degree of safety, and can effectively enlarge the safety window in the process of taking the drug.

An efficient method for the hydrolysis of potassium organotrifluoroborates promoted by montmorillonite K10

An efficient and non-expensive method for conversion of diverse potassium organotrifluoroborates to their corresponding boronic acids promoted by montmorillonite K10 using water as the reaction solvent is described. Further interconversion of potassium organotrifluoroborates to their corresponding boronic esters, via boronic acid intermediates was also successfully accomplished. The products were obtained in good yields, being the rate of hydrolysis influenced by the type of substituent present in the boronic acid.

Hexafluoro-2-propanol-assisted quick and chemoselective nitro reduction using iron powder as catalyst under mild conditions

Hexafluoro-2-propanol as the promoter for the quick nitro reduction using a combination of iron powder and 2 N HCl aqueous solution is reported. This methodology has several positive features, as it is of room temperature, remarkably short reaction time. A wide range of substrates including those bearing reducible functional groups such as aldehyde, ketone, acid, ester, amide, nitrile, halogens, even allyl, propargyl and heterocycles are chemoselectively reduced in good to excellent yields, even on gram scale. Notably, the highly selective reduction of 3-nitrophenylboronic acid is achieved quantitatively. The reduction is also tolerant of common protecting groups, and aliphatic nitro compound, 1-nitrooctane can be reduced successfully.

PROCESS FOR THE PREPARATION OF AMINOARYL- AND AMINOHETEROARYL BORONIC ACIDS AND ESTERS

The present invention relates to a process for the preparation of aminoaryl- and aminoheteroaryl boronic acids and esters thereof of formula (I) in high yield. The claimed process uses diarylketal formula (V) to generate an arylbromide of formula (III) in which the amino-group is protected as bisarylmethylidenimino-group, which is then transformed into a formula (I) compound.

Process for the preparation of aminoaryl- and aminoheteroaryl boronic acids and esters

The present invention relates to a process for the preparation of aminoaryl- and aminoheteroaryl boronic acids and esters of formula (I) in high yields The claimed process uses diarylketal formula (V) to generate an arylbromid of formula (III) in which the amino-group is protected as bisarylmethylidenimino-group:

Compositions for oxidatively dyeing keratin fibers and methods for using such compositions

Compositions for dyeing keratin fibers comprise (a) at least one keratin dyeing compound selected from aromatic systems which comprise at least one boronic acid or boronic ester moiety and which are capable of forming upon oxidation a nucleophile or an electrophile, (b) at least one additional keratin dyeing compound selected from the group consisting of auxiliary developers and auxiliary couplers, and (c) a cosmetically suitable medium. Methods for oxidatively dyeing keratin fibers comprise the steps of applying such compositions in the presence of an oxidizing agent and rinsing the hair. A hair coloring product in kit form comprises a first separately packaged container comprising a composition as described above and a second separately packaged container comprising an oxidizing agent.

Process for the preparation of aniline boronic acids and derivatives thereof

Production of anilineboronic acid derivatives (I) comprises converting an aniline compound (II) to a doubly protected derivative (III), metallating (III) and simultaneously or subsequently reacting it with a borate ester (IV) to give a protected anilineboronic acid ester (V), and deprotecting (V). Production of anilineboronic acid derivatives of formula (I) comprises converting an aniline compound of formula (II) to a doubly protected derivative of formula (III), metallating (III) and simultaneously or subsequently reacting it with a borate ester of formula (IV) to give a protected anilineboronic acid ester of formula (V), and deprotecting (V): [Image] PG : protecting group; R : H, halo, 1-20C alkyl or alkoxy, optionally substituted 6-12C aryl or aryloxy, heteroaryl or heteroaryloxy, optionally substituted 3-8C cycloalkyl, dialkylamino, diarylamino, alkylthio, arylthio, ester or acetal; X : H or halo; R1>-R3>H or optionally substituted 1-20C alkyl, or two of R1>-R3> can form a ring or another borate group.

Preparation, properties, and synthetic potentials of novel boronates in a fluorous version (fluorous boronates)

(equation presented) 4a-j R = aryl, alkenyl, alkyl A series of boronic acids were attached to a fluorous tag by esterification. Functional transformations of these boronates together with the fluorous Suzuki coupling reaction illustrated their usefulness in fluorous-phase techniques.