127580-92-1

Basic information

• Product Name: 4-(4-BROMOBENZOYL) MORPHOLINE
• Synonyms: 4-(4-BROMOBENZOYL) MORPHOLINE;(4-Bromophenyl)(morpholin-4-yl)methanone;(4-Bromophenyl)(morpholino)methanone;4-(Morpholine-4-carbonyl)bromobenzene
• CAS NO: 127580-92-1
• Molecular Formula: C₁₁H₁₂BrNO₂
• Molecular Weight: 270.12
• Product Categories: blocks;Bromides;Carboxes
• Mol File: 127580-92-1.mol

Chemical Properties

• Boiling Point: 398.7 °C at 760 mmHg
• Flash Point: 194.9 °C
• Appearance: /
• Density: 1.486 g/cm³
• Vapor Pressure: 1.45E-06mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -1.73±0.20(Predicted)
• CAS DataBase Reference: 4-(4-BROMOBENZOYL) MORPHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-BROMOBENZOYL) MORPHOLINE(127580-92-1)
• EPA Substance Registry System: 4-(4-BROMOBENZOYL) MORPHOLINE(127580-92-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• Hazardous Substances Data: 127580-92-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-Bromobenzoyl) Morpholine is used as a pharmaceutical intermediate for enhancing the solubility and bioavailability of certain pharmaceutical agents due to its basicity and polar character.
Used in Organic Synthesis:
4-(4-Bromobenzoyl) Morpholine is used as a chemical intermediate in organic synthesis for the production of various chemical compounds for commercial, pharmaceutical, or research purposes.

InChI:InChI=1/C11H12BrNO2/c12-10-3-1-9(2-4-10)11(14)13-5-7-15-8-6-13/h1-4H,5-8H2

Upstream product

• 61750-21-8 4-(4-Bromothiobenzoyl)morpholine 
• 110-91-8 morpholine 
• 586-76-5 4-Bromobenzoic acid 
• 1122-91-4 4-bromo-benzaldehyde 
• 586-75-4 4-chlorobenzoyl chloride 
• 15159-40-7 4-morpholinocarbonyl chloride 
• 148651-39-2 (4-bromophenyl)zinc iodide 
• 4394-85-8 4-morpholinecarboxaldehyde 
• 873-75-6 4-bromobenzenemethanol 
• 201230-82-2 carbon monoxide 
• 589-87-7 1,4-bromoiodobenzene 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 67-66-3 chloroform 
• 23328-69-0 4-chloromorpholine 

Downstream Products

• 1215169-46-2 (4-bromophenyl)-(3-methoxythiophen-2-yl)methanone 
• 1354349-41-9 (4-(2-benzoylbenzofuran-3-yl)phenyl)(morpholino)-methanone 
• 1413064-54-6 5-[4-(morpholine-4-carbonyl)-phenylamino]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole-4-carbonitrile 
• 1432450-87-7 (4-(4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-quinazolin-6-yl)phenyl)(morpholino)methanone 
• 58287-80-2 4-[(morpholin-4-yl)carbonyl]benzaldehyde 
• 1437785-89-1 C₁₉H₂₀N₂O₃ 
• 1593267-94-7 3-(4-(tert-butyl)phenyl)-1-(4-(morpholine-4-carbonyl)phenyl)prop-2-yn-1-one 
• 1631984-97-8 N-benzyl-N-cyano-4-(morpholine-4-carbonyl)benzamide 

Relevant articles and documents

A two-step continuous flow synthesis of amides from alcohol using a metal-free catalyst

Metal-free oxidative amination of aromatic alcohols in the presence of TBHP provides convenient access to amides in 86-96% yield under mild reaction conditions within 15 min in a two-step continuous flow reactor system. This method avoids expensive transition metal catalysts and integrates alcohol oxidation and amide bond formation, which are usually accomplished separately, into a single operation.

Heterobimetallic lanthanide/sodium phenoxides: Efficient catalysts for amidation of aldehydes with amines

Heterobimetallic lanthanide/sodium phenoxides were found to be efficient catalysts for amidation of aldehydes with amines under mild conditions. The reactivity follows the order Nd 2C6H3O iPr) 2C6H3O 2C 6H3O for phenoxide groups. In comparison with the corresponding monometallic complexes, heterobimetallic complexes show higher activity and a wider range of scope of amines. A cooperation of lanthanide and sodium in this process is proposed to contribute to the high activity of the present catalyst.

Metal-free n-Bu4NI-catalyzed direct synthesis of amides from alcohols and N,N-disubstituted formamides

A facile and efficient protocol for the synthesis of amides has been developed in the absence of transition metals. The reaction was performed with a catalytic amount of n-Bu4NI and aqueous TBHP as an oxidant. Various alcohols with N,N-disubstituted formamides were examined to furnish the desired products in good yields.

Palladium nanoparticles immobilized on an amine-functionalized MIL-101(Cr) as a highly active catalyst for oxidative amination of aldehydes

The present work reports the synthesis of well dispersed palladium nanoparticles immobilized on an amino functionalized nanoscale metal-organic framework MIL-101(Cr), by using a facile polyol method. The resulting Pd/NH2-MIL-101(Cr) nanocomposite is established to be an active heterogeneous catalyst for oxidative amination of aldehydes under solvent free conditions using hydrogen peroxide as an oxidant. The synthesized Pd/NH2-MIL-101(Cr) is characterized by powder X-ray diffraction, X-ray photoelectron spectroscopy, transmission electron microscopy, field emission scanning electron microscopy, Brunauer-Emmett-Teller (BET) surface area analysis, Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA) and atomic absorption spectroscopy (AAS). The catalyst could easily be recovered and recycled without any significant loss of its catalytic activity.

Preparation of N,N-dimethyl aromatic amides from aromatic aldehydes with dimethylamine and iodine reagents

Various N,N-dimethyl aromatic amides were obtained in good to moderate yields by the reaction of aromatic aldehydes with aqueous dimethylamine in the presence of molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH) at room temperature. Under the same conditions and using the same procedure, treatment of aromatic aldehydes and morpholine in the presence of DIH also provided the corresponding N-aroyl morpholines in good to moderate yields. Georg Thieme Verlag Stuttgart · New York.

Direct oxidative amination of aromatic aldehydes with amines in a continuous flow system using a metal-free catalyst

A novel method for metal-free oxidative amination of aromatic aldehydes and alcohols in the presence of H2O2/NaBr/H+ within 25 min in a continuous flow system has been developed. A series of different substrates were tested and the corresponding products were obtained in good yields .

Direct Amidation of Esters by Ball Milling**

The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.

NaI-mediated oxidative amidation of benzyl alcohols/aromatic aldehydes to benzamides via electrochemical reaction

In this research, we have developed a mild electrochemical process for oxidative amidation of benzyl alcohols/aromatic aldehydes with cyclic amines into the corresponding benzamides. This electroorganic synthetic method proceeds using NaI as a redox mediator under ambient temperature in undivided cell, providing more than 25 examples of amide products in moderate to good yields. The benefits of this reaction include one-pot synthesis, open air condition, proceed in aqueous media and no requirement of external conducting salt, base and oxidant.

Diverse functionalization of aryl halides mediated by bis(phenylsulfonyl)methane

A palladium-catalyzed coupling reaction of bis(phenylsulfonyl)methane and aryl halides was developed. A variety of bis(phenylsulfonyl)methyl arenes were prepared in good yields. The transformations of bis(phenylsulfonyl)methyl to methyl, trideuteriomethyl, ethyl, carboxyl, and other functional groups were demonstrated. The results provided a new approach to diverse functionalization of aryl halides.

A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.