397843-58-2

Usage

Uses

Used in Chemical Synthesis:
Boronic acid, [3-(4-morpholinylmethyl)phenyl](9CI) is used as a synthetic intermediate for the preparation of various organic compounds. Its boron-oxygen bond and hydrocarbon groups facilitate reactions with other molecules, making it a valuable component in the synthesis of complex organic structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Boronic acid, [3-(4-morpholinylmethyl)phenyl](9CI) is used as a building block for the development of new drugs. Its unique structure allows it to form stable complexes with biological targets, potentially leading to the discovery of novel therapeutic agents.
Used in Material Science:
Boronic acid, [3-(4-morpholinylmethyl)phenyl](9CI) is used as a component in the development of advanced materials. Its ability to form covalent bonds with other molecules can contribute to the creation of materials with specific properties, such as improved strength, flexibility, or chemical reactivity.
Used in Analytical Chemistry:
In analytical chemistry, Boronic acid, [3-(4-morpholinylmethyl)phenyl](9CI) is used as a reagent for the detection and quantification of certain compounds. Its selective binding properties can be exploited to develop sensitive and specific analytical methods for the identification of target molecules.

InChI:InChI=1/C11H16BNO3/c14-12(15)11-3-1-2-10(8-11)9-13-4-6-16-7-5-13/h1-3,8,14-15H,4-7,9H2

Upstream product

• 1025113-70-5 potassium 3-(morpholinomethyl)-phenyltrifluoroborate 
• 110-91-8 morpholine 
• 51323-43-4 (3-(bromomethyl)phenyl)boronic acid 

Downstream Products

• 1617499-05-4 3-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-5-[3-(morpholinomethyl)phenyl]pyridin-2-amine 
• 1617499-00-9 3-(1-isopropyltriazol-4-yl)-5-[3-(morpholinomethyl)phenyl]pyridin-2-amine 
• 1239441-34-9 C₂₀H₂₀N₆O 

Relevant academic research and scientific papers

Efficient hydrolysis of organotrifluoroborates via silica gel and water

(Chemical Equation Presented) A general, mild, and efficient method for the hydrolysis of organotrifluoroborates to unveil boronic acids using silica gel and H2O was developed. This method proved to be tolerant of a broad range of aryl-, heteroaryl-, alkenyl-, and alkyltrifluoroborates as well as structurally diverse aminomethylated organotrifluoroborates.As anticipated, electron-rich substrates provided the corresponding boronic acids more readily than electron-poor substrates, owing to the resonance-stabilized difluoroborane intermediate. The method developed was expanded further for the conversion of organotrifluoroborates to the corresponding boronate esters. 2009 American Chemical Society.

Pyrrolopyrimidines and Pyrrolopyridines

Compounds of formula I in free or salt or solvate form, wherein X, T1, T3 and T4 have the meanings as indicated in the specification, are useful for treating diseases mediated by the ALK-5 and/or ALK-4 receptor. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.

Preparation and uses of conjugated solid supports for boronic acids

The invention provides novel solid supports comprising dihydroxyalkyl aminoalkyl and dihydroxyalkylaminobenzyl groups, and methods for making and using them. The supports are particularly useful for immobilizing and derivatizing functionalized boronic acids for use in solid phase synthesis, such as those used in combinatorial chemistries. The compositions and methods of the invention are also useful as scavenger solid supports, e.g., in solution-phase parallel synthesis of small molecule libraries, and for use in resin-to-resin transfer reactions via phase transfer of solid supported boronic acids under both aqueous and anhydrous conditions. The methods of the invention provide convergent solid-phase synthesis of symmetrically or unsymmetrically functionalized compounds, such as biphenyl compounds. Also provided are synthesizer devices, e.g., semiautomated parallel synthesizers.

Universal solid-phase approach for the immobilization, derivatization, and resin-to-resin transfer reactions of boronic acids

Boronic acid-containing molecules are employed in a broad range of biological, medicinal, and synthetic applications. These compounds, however, tend to be difficult to handle by solution-phase methods. Herein, this problem is addressed with the development of the first general solid-phase approach for the derivatization of functionalized boronic acids. This approach is based on the use of a diethanolamine resin anchor that facilitates boronic acid immobilization by avoiding the need for exhaustive removal of water in the esterification process. The immobilization of a wide variety of boronic acids onto N,N-diethanolaminomethyl polystyrene (DEAM-PS, 1) can be performed within minutes by simple stirring in anhydrous solvents at room temperature. Evidence for the formation of a bicyclic diethanolamine boronate with putative N-B coordination was shown by 1H NMR analysis of DEAM-PS-supported p-tolylboronic acid. The hydrolytic cleavage of the same model boronic acid from the DEAM-PS resin was studied by UV spectroscopy. Hydrolysis and attachment were shown to occur under a rapidly attained equilibrium, and a large excess of water (> 32 equiv) is required to effect a practically quantitative release of boronic acids from DEAM-PS. Despite their relative sensitivity to water and alcohols, DEAM-PS-bound arylboronic acids functionalized with a formyl, a bromomethyl, a carboxyl, or an amino group can be transformed in good to excellent yields into a wide variety of amines, amides, anilides, and ureas, respectively. Ugi multicomponent reactions on DEAM-PS-supported aminobenzeneboronic acids, derivatization of multifunctional arylboronic acids, and sequential reactions can also be carried out efficiently. These new DEAM-PS-supported arylboronic acids can be employed directly into resin-to-resin transfer reactions (RRTR). This type of multiresin process helps eliminate time-consuming cleavage and transfer operations, thereby considerably simplifying the outlook of combinatorial library synthesis by manual or automated means. This concept was illustrated by a set of optimized procedures for the Suzuki cross-coupling and the borono-Mannich reactions.