6291-23-2

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
4-Morpholinophenol is used as a building block for the synthesis of pharmaceuticals and agrochemicals, contributing to the development of new drugs and agricultural products.
Used in Chemical Production:
4-Morpholinophenol is used as an intermediate in the production of various chemicals, such as dyes, pigments, and rubber chemicals, enhancing the properties and performance of these materials.
Used in Skin Care and Cosmetic Products:
Due to its antioxidant and anti-inflammatory properties, 4-morpholinophenol is a potential candidate for use in skin care and cosmetic products, offering benefits for skin health and protection.
However, it is crucial to handle and use 4-morpholinophenol with caution, as it may present health and environmental hazards due to its toxic and irritant properties. Proper safety measures should be taken to minimize risks associated with its use.

InChI:InChI=1/C10H13NO2/c12-10-3-1-9(2-4-10)11-5-7-13-8-6-11/h1-4,12H,5-8H2

Upstream product

• 123-30-8 4-amino-phenol 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 106-41-2 4-bromo-phenol 
• 6793-92-6 p-benzyloxyphenylbromide 
• 36603-49-3 4-(tetrahydropyran-2'-yloxy)-1-bromobenzene 
• 110-91-8 morpholine 
• 540-38-5 p-Iodophenol 
• 70291-67-7 N-(4-chlorophenyl)morpholine 

Downstream Products

• 1149748-56-0 C₁₅H₂₂BrNO₂ 
• 67914-39-0 4-{4-[2-(2,4-dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-morpholine 

Relevant academic research and scientific papers

Preparation and application of aminourea-sensitive amine oxidase inhibitor

The invention provides preparation and application of an aminourea-sensitive amine oxidase inhibitor. Specifically, the invention discloses a compound as shown in a formula I which is described in thespecification or a stereoisomer or racemate or a pharmaceutically acceptable salt thereof. The invention also discloses the capability of the compound in inhibition of aminourea-sensitive amine oxidase.

N-(2-Phenoxy)ethyl imidazo[1,2-a]pyridine-3-carboxamides containing various amine moieties: Design, synthesis and antitubercular activity

Seven 2,6-disubstituted N-(2-phenoxy)ethyl imidazo[1,2-a]pyridine-3-carboxamide series containing various amine moieties were designed and synthesized as new anti-TB agents. Many of them show excellent in vitro activity against both drug-sensitive MTB strain H37Rv and two MDR-MTB clinical isolates (MIC: 0.002–0.030 μg/mL). Compounds 2f, 5e and 5g display acceptable safety and pharmacokinetic profiles, opening a new direction for further development.

Ultrafine hybrid Cu2O-Fe2O3 nanoparticles stabilized by hexaphenylbenzene-based supramolecular assemblies: A photocatalytic system for the Ullmann-Goldberg coupling reaction

Ultrafine hybrid Cu2O-Fe2O3 NPs have been prepared using the supramolecular assemblies of hexaphenylbenzene (HPB) derivative 3 as nanoreactors and stabilizers. The as-prepared hybrid Cu2O-Fe2O3 NPs serve as an efficient and recyclable photocatalytic system for carrying out C-N coupling between aryl halides and various amines (aliphatic, aromatic and N-heterocyclic) at room temperature in mixed aqueous media under visible light irradiation. Amazingly, Cu2O-Fe2O3 NPs also exhibited high efficiency in the reactions involving the synthesis of biologically important N-substituted carbazole derivatives. The work being presented in this article demonstrates the preparation of a 'dip strip' coated with the as-prepared catalytic system and utilization of this paper strip as a recyclable and portable heterocatalytic system for carrying out the Ullmann-Goldberg coupling.

Buchwald-Hartwig amination reaction of aryl halides using heterogeneous catalyst based on Pd nanoparticles decorated on chitosan functionalized graphene oxide

In this work, graphene oxide was functionalized with chitosan (GO-Chit) followed by a simple approach for immobilization of palladium nanoparticles onto a chitosan grafted graphene oxide surface. The Pd-nanocomposite (GO-Chit-Pd) was characterized using Transmission Electron Microscopy (TEM), Fourier transforms infrared spectroscopy (FT-IR), and X-ray diffraction (XRD) measurements. The catalytic activity of the prepared heterogeneous graphene oxide functionalized chitosan-palladium (GO-Chit-Pd) was investigated in term of C-N coupling reaction (Buchwald-Hartwig amination reaction of aryl halides) yielding products of N-arylamines. The easy purification, convenient operation, and environmental friendliness, combined with a high yield, render this method viable for use in both laboratory research and larger industrial scales. Studying the reusability of the catalyst in this work showed that it could be reused for five times without obvious loss in catalytic activity.

Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions

The combination of Cu(acac)2 and N,N′-bis(4-hydroxyl-2,6-dimethylphenyl)oxalamide (BHMPO) provides a powerful catalytic system for hydroxylation of (hetero)aryl halides. A wide range of (hetero)aryl chlorides bearing either electron-donating or -withdrawing groups proceeded well at 130 °C, delivering the corresponding phenols and hydroxylated heteroarenes in good to excellent yields. When more reactive (hetero)aryl bromides and iodides were employed, the hydroxylation reactions completed at relatively low temperatures (80 and 60 °C, respectively) at low catalytic loadings (0.5 mol % Cu).

Efficient microwave-assisted Pd-catalyzed hydroxylation of aryl chlorides in the presence of carbonate

An efficient microwave-assisted, palladium-catalyzed hydroxylation of aryl chlorides in the presence of a weak base carbonate was developed, which rapidly converts aryl and heteroaryl chlorides to phenols, and can be used when the aryl chloride is functionalized with a ketone, aldehyde, ester, nitrile, or amide.

(t-Bu)2PN=P(i-BuNCH2CH2)3N: New efficient ligand for palladium-catalyzed C-N couplings of aryl and heteroaryl bromides and chlorides and for vinyl bromides at room temperature

(Chemical Equation Presented) By employing Pd(OAc)2, Cs 2CO3, or NaOH, and the new ligand (t-Bu) 2PN=P(i-BuNCH2CH2)3N (3a), an electronically diverse array of aryl bromides and chlorides possessing base-sensitive substituents (nitro, ester, and keto) provide coupling products with bulky aryl amines in good to excellent yields. Aryl halides possessing other functional groups including cyano, amino, trifluoromethyl, and phenol, coupled with equal ease, producing highly functionalized amines in good to excellent yields. Moreover, an aryl chloro group can be preserved in the presence of a bromo substituent under our reaction conditions. BOC-protected amines also participated efficiently. Heterocyclic bromides and chlorides underwent clean couplings with amines in excellent yields. An important strength of our protocol is the use of lower palladium loadings than those reported earlier, without compromising yields. The air-stable palladium complex (η3-cinnamyl)PdCl·(3a) (5) was also employed successfully in C-N coupling reactions while the crotyl analogue was less efficacious. The 3a/Pd(OAc)2 catalyst system promotes, for the first time, efficient coupling of vinyl bromides with a variety of amines to produce imines and enamines at room temperature.

Palladium/proazaphosphatrane-catalyzed amination of aryl halides possessing a phenol, alcohol, acetanilide, amide or an enolizable ketone functional group: Efficacy of lithium bis(trimethylsilyl)amide as the base

A commercially available catalyst system comprising Pd(OAc)2 or Pd2(dba)3 and the proazaphosphatrane ancillary ligand P(i-BuNCH2CH2)3N (1) for the amination of aryl halides substituted with a phenol, alcohol, acetanilide, amide or ketone group containing an enolizable hydrogen is described. The reaction is performed in the presence of LiN(SiMe3)2 as the base. Other bases tested were either less effective or completely non-functional.

Scope and utility of CsOH·H2O in animation reactions via direct coupling of aryl halides and sec-alcyclic amines

Direct coupling of aryl halides with sec-alicyclic amines promoted by CsOH·H2O in DMSO to the corresponding aryl substituted amines, with good to excellent yields, is reported herein. A variety of aryl halides and sec-alicyclic amines with a broad range of electronic diversity and functional groups was studied in this transformation, thus offering general applicability in organic synthesis.

Rapid and Efficient Microwave-Assisted Amination of Electron-Rich Aryl Halides without a Transition-Metal Catalyst

Equation presented. A rapid and direct amination of aryl halides has been developed in good to high yields under microwave irradiation without a transition-metal catalyst. This reaction is a particularly powerful method for the coupling of electron-rich aryl halides with various amines. In some cases, the excellent regioselectivity could be observed, which facilitated the preparation of meta-substituted anilines from ortho- or para-substituted phenylhalides. In addition, a mechanism via the interesting benzyne intermediate has been proposed.