21854-73-9

Usage

Usage

Production of pharmaceuticals and dyes

Physical state

Yellow solid at room temperature

Solubility

Insoluble in water, soluble in organic solvents (e.g., ethanol, acetone)

Odor

Strong smell

Skin and eye contact

Irritant

Inhalation and ingestion hazards

Causes respiratory and digestive system irritation

Environmental impact

Harmful to aquatic life

Handling and disposal

Requires caution and proper procedures

Upstream product

• 108-94-1 cyclohexanone 
• 100-52-7 benzaldehyde 
• 106-47-8 4-chloro-aniline 
• 1613-89-4 (E)-N-benzylidene-4-chloroaniline 

Downstream Products

• 164026-52-2 2-amino-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 

Relevant academic research and scientific papers

Direct-type catalytic three-component Mannich reaction in aqueous media

Bismuth triflate catalyzed direct-type Mannich reaction of cyclohexanone, aromatic aldehyde, and aromatic amine proceeded smoothly in water to afford the corresponding β-amino ketone with very good yield and moderate to good anti selectivity.

Basic functionalized ionic liquid catalyzed One-pot mannich-type reaction: Three component synthesis of β-Amino carbonyl compounds

Three-component Mannich-type reaction of cyclohexanone, aromatic aldehydes, and aromatic amines was catalyzed by a basic functionalized ionic liquid, 1-butyl-3-methylimidazolium hydroxide ([bmim][OH]), at room temperature to give various β-amino carbonyl compounds in high yields. The ionic liquid, which is environmentally friendly, can be recycled at least 5 times without significant loss of activity.

Designing a novel tetradentate polyoxometalate eco-catalyst for the synthesis of β-aminocyclohexanone derivatives in water

The synthesis of a series of known β-aminocyclohexanones has been accomplished using pentaerythrityl tetramethyl imidazolium phosphotungstate (C(MIM-PTA)4) as a new tetradentate acidic catalyst. It was prepared via condensation of pentaerythrityl tetrabromide with methyl imidazole. Then, bulky anion H2PW12O401? was substituted with Br? in the structure. This tetradentate catalyst provides designable cations and anions. Anions have two types of acids, acidic protons, and metals with Lewis acidity. In order to test the efficient catalytic behavior of the tetradentate catalyst, a controlled reaction was performed using benzaldehyde, aniline and cyclohexanone. Imine from the condensation of benzaldehyde and aniline was observed in the absence of ionic catalyst instead of desired products. Thus, this reaction would be attractive because of the time, energy, and raw material saving considerations because of the absence of isolation of intermediates and stereospecificity. The catalyst shows high catalytic activity such that after four recycles the product was obtained with high yield and purity. This reaction was performed at room temperature. Although high temperature could improve the reaction rate, it contributes to side reactions and oxidation of aldehyde and amine. The catalyst was characterized by elemental analysis, FT-IR spectroscopy, 1H NMR, 13C NMR, and TGA.

H3PW12O40 supported on functionalized polyoxometalate organic-inorganic hybrid nanoparticles as efficient catalysts for three-component Mannich-type reactions in water

Two new types of catalyst were synthesized by the immobilization of H3PW12O40 (HPW12) on the surface of organic-inorganic polyoxometalate nanoparticles of H6Cu2[PPDA]6[SiW9Cu3O37]·12H2O (HybPOM) (PPDA = p-phenylenediamine) and Go/Fe3O4/HybPOM nanoparticles. These catalysts were characterized by thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), energy dispersive X-ray analysis (EDX) and alternating gradient force magnetometry (AGFM). The IR spectroscopy as well as XRPD reveal that HPW12 were immobilized on the support. The potentiometric titration with n-butylamine reveal that the catalysts can be classified as strong acids. The results show that the particles are mostly spherical in shape and have an average size in the range of 20-50 nm. The catalytic activities of the catalysts were probed through one-pot three-component Mannich-type reactions of aldehydes, amines and ketones in water at room temperature. The catalysts were re-used at least five times without any loss of their high catalytic activity.

Mesoporous silica nanoparticles (MSNs) as an efficient and reusable nanocatalyst for synthesis of β-amino ketones through one-pot three-component Mannich reactions

Mesoporous silica nanoparticles (MSNs) proved efficient and reusable in the catalytic synthesis of β-amino ketones, through three-component Mannich reaction of ketones, aromatic aldehydes and aromatic amines under solvent-free conditions. Simple reaction conditions coupled with simple work-ups, makes this methodology a superior option for the synthesis of such β-amino ketones.

Polyelectrolyte Br?nsted acid catalyzed three-component Mannich reactions accelerated by emulsion

An effective polyelectrolyte Br?nsted acid (polyacrylic acid) catalyzed three-component Mannich reaction accelerated by emulsion has been developed. The results demonstrated that the polyacrylic acid (PAA) provided the best catalytic activity in water because of the formation of emulsions during the reaction. This newly developed simple catalyst could be recycled at least five times without any loss of activity.

An environmentally friendly, photocontrollable and highly recyclable catalyst for use in a one-pot three-component Mannich reaction

An environmentally friendly, photocontrollable and highly recyclable catalyst (ZrOPPAZOSO3H) has been synthesized by the immobilization of 4-[4-(6-phosphonic acid-hexanoxyl)phenylazo]benzenesulfonic acid onto zirconium phosphonate. This catalyst was characterized by Fourier transform infrared, scanning electron microscopy, X-ray powder diffraction, nitrogen adsorption-desorption and UV-vis analyses. The catalytic activity of ZrOPPAZOSO3H was investigated towards the one-pot three-component Mannich-type reaction of benzaldehyde, aniline and cyclohexanone in water at room temperature, and gave excellent yields. Interestingly, the catalytic activity could be regulated by photoirradiation. Furthermore, upon completion of the reaction, the product could be readily separated by extraction, and the water phase reused in the next run. Lastly, the catalyst could be readily recovered by centrifugation and reused up to six times without any discernible impact on its activity.

H5CoW12O40@nanosilica: A green, bifunctional, heterogeneous nanocatalyst for one-pot three-component Mannich reaction in water

Abstract 12-Tungestocobaltic acid, H5CoW12O40, was immobilized on nanosilica from rice husk ash to produce H5CoW12O40@nanosilica as a bifunctional nanocatalyst. The TEM result showed that the particles are mostly spherical in shape, and that they have an average size of approximately 10 nm. The catalytic activity of this catalyst was investigated in Mannich reaction of various aldehydes, ketones, and amines in water. This rapid procedure afforded structurally diverse β-amino ketones in high to excellent yields. Short reaction time, simple work-up procedure, elimination of toxic solvents, and low catalyst loading are the advantages of this procedure.

Bronsted acid-surfactant-combined catalyst for the Mannich reaction in water

A series of Bronsted acid-surfactant-combined catalysts (BASCs) functionalised with different acids have been synthesized and applied to catalyze the three-component Mannich reaction with aldehyde, acetone and amine at 25 °C in water. The effects of cation tail length and ions of the ionic liquid and the recyclability of the catalysts and BASC acidity (H0) were investigated. The results demonstrated that the 3-(N,N- dimethyloctylammonium) propanesulfonic acid toluene sulfate ([DOPA][Tos]) provide the best catalytic activity because of the formation of emulsions during the reaction. The catalytic procedure was simple and the catalyst could be recycled 9 times by simple separating processes without noticeably decreasing the catalytic activity. The Royal Society of Chemistry 2014.

An efficient synthesis of β-aminoketone compounds through three-component Mannich reaction catalyzed by calcium chloride

Various β-aminoketones were synthesized in a three-component reaction of ketones, aldehydes, and amines in the presence of calcium chloride as catalyst in ethanol in high yields as compared to other synthetic methods. The advantages of this new method are a short reaction time (2 h), high yields, easy workup, convenience, low cost, and eco-friendly protocol. Springer-Verlag 2011.