856-19-9

Usage

Chemical class

Ketones

Physical form

Pale yellow oil

Odor

Pungent

Uses

Production of pharmaceuticals and research chemicals

Psychoactive effects

Euphoria, increased energy, heightened sensory perception

Health risks

Increased heart rate, overheating, potential overdose, drug-related deaths

Public health concern

Yes

Upstream product

• 100-52-7 benzaldehyde 
• 62-53-3 aniline 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 959-23-9 4'-methoxychalcone 

Relevant academic research and scientific papers

Synthesis of β-Amino Ketones using graphene oxide: a benign carbonaceous acid catalyst for Mannich reaction

Abstract: Simple and easily preparable graphene oxide (GO) is used as a straightforward carbocatalyst for the synthesis of β-amino ketones via a 3-component Mannich reaction under mild condition. The native GO is acting as a carbonaceous solid Br?nsted acid catalyst without any special functionalization, yielding a spectrum of β-amino ketones under metal-free conditions. The present catalytic method offers a benign and simple procedure without any hazardous workup, and chromatographic purification resulted in an excellent yield of β-amino ketones. The catalyst has shown good sustainability up to 6 consecutive catalytic cycles without any significant loss in its activity. The stability of the recovered catalyst is proved by analytical techniques such as FT-IR, PXRD, SEM, and TEM. This mild solid-acid catalyst offers an alternative and sustainable approach to get synthetically essential β-amino ketones under greener conditions. Graphical abstract: [Figure not available: see fulltext.].

Ionic liquid-immobilized proline(s) organocatalyst-catalyzed one-pot multi-component Mannich reaction under solvent-free condition

A highly efficient clean and simple methodology has been established for the one-pot Mannich reaction using ionic liquid-immobilized proline(s) organocatalyst under solvent-free conditions. The three components comprising substituted acetophenones, substituted aromatic aldehydes and substituted aromatic amines underwent Mannich reactions in the presence of 7?mol% of ionic liquid-immobilized proline(s) organocatalyst to provide β-amino carbonyl compounds in 2–3?h at room temperature with excellent yields. This methodology provides several advantages such as mild reaction conditions, short reaction time, low catalyst loading percentage, multi-component approach, transition metal-free and solvent-free synthesis. The ionic liquid-immobilized proline(s) organocatalyst was recycled and reused five times without a significant loss of its catalytic activity.

Cellulose-Supported Ionic Liquid Phase Catalyst-Mediated Mannich Reaction

Cellulose-supported ionic liquid phase (SILP) catalyst containing a camphor sulfonate anion with a pendant ferrocenyl group was prepared and characterised with different analytical techniques such as Fourier-transform infrared, Fourier-transform Raman, and cross polarization-magic angle spinning (CP-MAS) 13C NMR spectroscopy, X-ray diffraction, scanning electron microscopy, and thermogravimetric analysis. The SILP catalyst displayed excellent catalytic activity in the synthesis of β-amino carbonyl compounds by Mannich reaction. Recycling studies revealed that SILP catalyst could be reused six times without significant decrease in catalytic activity.

Solvent strategy for unleashing the Lewis acidity of titanocene dichloride for rapid Mannich reactions

The remarkable activation effect of alcohol solvent on kinetically inert titanocene dichloride was found to promote rapid three-component Mannich reactions. NMR and ESI-MS analyses as well as a control experiment of catalytic active species elucidated that the coordination of MeOH to the titanocene moiety unleashed the Lewis acid [Cp2Ti(OMe)2] and Br?nsted acid HCl, which led to the enhanced catalytic activity of [Cp2TiCl2].

Ultrasound-promoted synthesis of-Amino carbonyl compounds via a mannich reaction catalyzed by ionic liquids

Background: Mannich reaction is one of the most important carbon-carbon bond formation reactions in organic synthesis. Traditional methods require a large amount of ungreen catalysts or much longer reaction time, which limits the scope of their application. So, a recyclable catalyst with high activity and selectivity is highly appreciated, and the highly shortened reaction time is also very appealing. Methods: An efficient and facile process to prepare a series of -Amino carbonyl compounds was found via Mannich reactions catalyzed by caprolactam-based Br?nsted acidic ionic liquids under ultrasonic irradiation. Results: [Capl][BF4] was the most effective catalyst in the Mannich reaction, and good yields was gained within 2-6 h. The activity and stability of the catalyst was maintained very well even after five times, and ultrasound can effectively shorten the reaction time and enhance the yield at ambient condition. Conclusion: A convenient procedure for Mannich reaction using acidic ILs catalyst under ultrasonic irradiation has been designed with many superiorities, such as simple manipulation, less reaction time and high yields. The Mannich reaction takes place in no presence of organic solvents such as toluene or ethanol, etc. The new synthetic method reported in this paper would make appreciable contribution to the subject of environmental friendly chemistry and it is available for industrial applications.

Deep Eutectic Solvent as a Recyclable Catalyst for Three-Component Synthesis of β-Amino Carbonyls

We have reported one-pot, three-component Mannich type reaction of aldehyde, amines and ketone (acetone and acetophenones), catalyzed by deep eutectic solvent (choline chloride/zinc chloride) at room temperature to give β-amino carbonyls in good yields. The catalyst could be recycled at least four times without remarkable decrease in its catalytic activity. The general method is easy, fast and environmental friendly.

A magnetic solid sulfonic acid modified with hydrophobic regulators: An efficient recyclable heterogeneous catalyst for one-pot aza-Michael-type and Mannich-type reactions of aldehydes, ketones, and amines

Two convenient green protocols for the synthesis of β-amino ketones have been developed which involve one-pot aza-Michael-type and Mannich-type reactions of a series of aldehydes, ketones, and amines in the presence of a catalytic amount of the magnetic solid sulfonic acid catalyst, Fe3O4@SiO2@Me&Et-PhSO3H, at room temperature. The catalyst can be reused four times without loss of activity.

Synthesis of β-aminoketone by reaction of amine and activated chalcone in microwave irradiation

A simple and efficient protocol has been developed for the aza-Michael addition of amines to a variety of activated olefins or chalcones under microwave irradiation. Under these conditions, there is a significant decrease in the reaction time while considerable increase in the yield and purity of the products can be obtained.

Salicylato titanocene complexes as cooperative organometallic lewis acid and bronsted acid catalysts for three-component mannich reactions

A binary acid system has been developed that features an air-stable organometallic precursor, titanocene dichloride, and simple organic cooperative Bronsted acids, which allowed for mild and highly efficient Mannich reactions of both aryl and alkyl ketones with excellent yields and satisfactory diastereoselectivity. Mechanistic studies, including 1H NMR titration, X-ray structure analyses as well as isolation of catalytically active species, elucidated the dramatic synergistic effects of this new binary acid system.

Ionic amino acids: Application as organocatalysts in the aza-Michael reaction

The ethyl methyl imidazolium salts of amino acids, [emim][AA], have been used as catalysts in the aza-Michael reaction. Furthermore, when chiral amino acids were used, a stereoselective reaction was achieved. The mechanism of the transformation was verified by the detection of a key intermediate by electrospray ionization mass spectroscopy (ESI-MS).