857-90-9

Usage

Appearance

Yellow crystalline solid

Usage

Intermediate in the synthesis of various organic compounds

Applications

Production of pharmaceuticals, reagent in organic synthesis, preparation of dyes and pigments

Hazardous

Yes, should be handled with care and following proper safety protocols.

Upstream product

• 100-52-7 benzaldehyde 
• 62-53-3 aniline 
• 100-19-6 (4-nitrophenyl)ethanone 

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.].

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.

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].

Ethane-1,2-diaminium hydrogen sulfate: Recyclable organocatalyst for onepot synthesis of β-amino ketones by a three-component Mannich reaction

Ethane-1,2-diaminium hydrogen sulfate was synthesised and characterised by NMR and elemental analysis techniques, and found to exhibit high catalytic efficiency towards one-pot Mannich-type reactions of ketones with aromatic aldehydes and aromatic amines in ethanol. This method has the advantages of mild conditions, availability of starting materials, compatibility with a variety of functionalities, and simple work-up procedures. This catalyst also shows good recyclability and reusability.

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.

PEG-OSO3H as an efficient and recyclable catalyst for the synthesis of β-amino carbonyl compounds via the Mannich reaction in PEG-H2O

Sulfuric acid-modified polyethylene glycol 6000 (PEG-OSO3H) was applied as an efficient and recyclable catalyst for the synthesis of β-amino carbonyl compounds via the Mannich reaction between aldehydes, aromatic ketones and aromatic amines at room temperature using PEG400-H 2O (1:1) as environment-friendly solvents. The reactions were completed in short times and mild reaction conditions with good to excellent yields.

Mannich reactions catalyzed by perchloric acid in Triton X10 aqueous micelles

Perchloric acid can efficiently catalyze the one-pot, three-component Mannich reactions of ketones with aromatic aldehydes and aromatic amines in Triton X10 aqueous micelles at room temperature. This protocol has several advantages such as excellent yields, mild conditions, clear reaction profile and simple work-up procedure.

Cerium chloride (CeCl3·7H2O) as a highly efficient catalyst for one-pot three-component Mannich reaction

We have demonstrated the use of CeCl3·7H2O as highly efficient catalyst for one-pot threecomponent Mannich reaction to afford β-amino carbonyl compounds in good to excellent yield within shorter period of reaction time. The process is mild, efficient, environmentally benign with the use of little amount of catalyst.

Pronounced catalytic effect of a micellar solution of sodium dodecylsulfate (SDS) upon a three-component reaction of aldehydes, amines, and ketones under neutral conditions

A micellar solution of anionic, cationic or neutral surfactants can be used as an excellent medium for three-component Mannich reactions of aldehydes, amines, and ketones at room temperature. Sodium dodecylsulfate turned out to efficiently catalyze the reaction in neutral pure water (pH ≈ 7), and the corresponding desired β-amino ketones precipitate while the reactions proceedes. This method provides a novel and improved modification of the three-component Mannich reaction in terms of mild reaction conditions, clean reaction profile, improved yields, and excellent regio- and diastereoselectivities with a simple workup. Interesting examples of click chemistry under neutral conditions in water were observed. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.

Novel one-pot Cu-nanoparticles-catalyzed Mannich reaction

Recyclable heterogeneous Cu-nanoparticles efficiently catalyzed the one-pot three-component Mannich reaction of ketones, aromatic aldehydes and amines in methanol. This method provides a novel and improved method for obtaining β-amino carbonyl compounds in terms of good yield with little catalyst loading.