1669-48-3

Usage

Physical state

Yellow crystalline solid

Uses

Intermediate in the synthesis of pharmaceuticals and agrochemicals; production of dyes and pigments

Biological activities

Antibacterial and antifungal properties

Hazards

Toxic and can cause irritation to skin, eyes, and respiratory system

Upstream product

• 28918-06-1 2-(4-nitrobenzylidene)-1,3-diphenylpropane-1,3-dione 
• 555-16-8 4-nitrobenzaldehdye 
• 70-11-1 α-bromoacetophenone 
• 98-86-2 acetophenone 
• 636-98-6 p-nitrobenzene iodide 
• 37442-45-8 ethyl 2-(hydroxy(phenyl)methyl)propenoate 
• 619-73-8 4-nitrobenzyl chloride 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 100-52-7 benzaldehyde 
• 1222-98-6 4-nitrochalcone 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 2960-55-6 (E)-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one 
• 49678-08-2 3-(4-nitrophenyl)-propenal 

Downstream Products

• 110655-60-2 2-(p-nitrophenyl)-1-phenylpropanol 
• 57254-06-5 2-bromo-3-(4-nitro-phenyl)-1-phenyl-propan-1-one 
• 62056-36-4 3-(4-nitro-phenyl)-1-phenyl-propan-1-ol 

Relevant academic research and scientific papers

Applications of N1-long-chain alkyl-N3-piperidine ethylimidazole salt

The invention provides applications of an N1-long-chain alkyl-N3-piperidine ethylimidazole salt, wherein the ionic liquid has surface activity and double alkalinity, and can catalyze the synthesis ofchalcone compounds. The method for synthesizing a chalcone compound under the catalysis of the ionic liquid comprises: mixing substituted benzaldehyde, substituted acetophenone and water, adding an ionic liquid, and carrying out a reaction; and after the reaction is finished, carrying out separation purification to obtain a product chalcone compound, wherein the separated catalyst-containing solution can be applied. According to the invention, the problems of strong corrosivity of composite catalyst systems such as ionic liquids/alkalis, ionic liquids/acid and the like, and high ionic liquid consumption, low yield and the like in the chalcone preparation process only using alkaline ionic liquid catalysts are overcome, and the reaction yield in the catalytic synthesis of chalcone compoundsreaches more than 85%; and the method for preparing the chalcone compound through catalysis has characteristics of easy and convenient operation, easy product separation, environmentally friendly solvent and repeated use of the catalyst.

Organocatalyzed biomimetic selective reduction of c=c double bonds of chalcones

In this article, we reported a biomimetic approach for chemoselective reduction of C=C double bonds in chalcones under metal and acid free conditions, that relies on olefin activation by hydrogen bond formation. The process requires only catalytic amount of ephedrine as hydrogen bond donor and utilizes Hantzsch esters for transfer hydrogenation.

Pd anchored on C3N4 nanosheets/reduced graphene oxide: An efficient catalyst for the transfer hydrogenation of alkenes

In this work, a porous g-C3N4 nanosheets/reduced graphene oxide (rGO) composite was synthesized via the hydrothermal co-assembly of GO and g-C3N4 nanosheets (g-C3N4 NS). Compared with g-C3N4 NS, rGO and bulk g-C3N4/rGO, the g-C3N4 NS/rGO supported Pd nanocatalyst displayed a remarkable catalytic activity for the hydrogenation of alkenes with formic acid and formates as the hydrogen source at atmospheric pressure. Among all the as-prepared Pd-g-C3N4 NS/rGO catalysts, the optimized Pd-g-C3N4 NS/rGO20 exhibited the highest turnover frequency of 133 mol mol-1 Pd h-1, which is among the highest value reported in documents. 99% conversion and 99% selectivity were achieved after 30 min reaction at 30 °C for the hydrogenation of nitrobenzene. In addition, Pd-g-C3N4 NS/rGO20 exhibited an excellently high stability after five successive cycles without significant loss of its catalytic activity.

Dirhodium(ii)/P(t-Bu)3 catalyzed tandem reaction of α,β-unsaturated aldehydes with arylboronic acids

Phosphine ligated dirhodium(ii) acetate is advocated as a catalyst for the synthesis of aryl alkyl ketones by the tandem reaction of α,β-unsaturated aromatic or aliphatic aldehydes with arylboronic acids. This tandem procedure included arylation followed by the isomerization reaction. This method exhibits good functional group tolerance and has a broad substrate scope. With the conjugated aldehydes, the one-step synthesis of γ,δ-unsaturated ketones was realized through this reaction. It is noteworthy that the length of the Rh-P bond is an important factor affecting catalytic reactions. The comparative analysis of the crystal structures of axially alkylphosphane and arylphosphane ligated dirhodium(ii) acetate revealed that the shorter Rh-P bond length favors the isomerization process as compared to the longer one. In addition, the dirhodium(ii) compound can be recovered after the completion of the reaction.

Cobalt-Catalyzed α-Alkylation of Ketones with Primary Alcohols

An ionic cobalt-PNP complex is developed for the efficient α-alkylation of ketones with primary alcohols for the first time. A broad range of ketone and alcohol substrates were employed, leading to the isolation of alkylated ketones with yields up to 98%. The method was successfully applied to the greener synthesis of quinoline derivatives while using 2-aminobenzyl alcohol as an alkylating reagent.

Metal-Free Domino One-Pot Decarboxylative Cyclization of Cinnamic Acid Esters: Synthesis of Functionalized Indanes

Trifluoroacetic acid promoted unprecedented domino reaction for the synthesis of diverse indanes starting from simple cinnamic acid esters is described. Their formation can be explained via acid triggered decarboxylation of cinnamic acid esters and subsequent inter/intramolecular cyclization. Overall process involves in the intramolecular cleavage of two σ-bonds (C-O and C-C) and inter/intramolecular construction of two/one C-C σ-bond(s). Significantly, this protocol was successful without the aid of any metal salts.

Ruthenium-catalyzed conjugate hydrogenation of ?±,?2-enones by in situ generated dihydrogen from paraformaldehyde and water

Notwithstanding that the highly selective hydrogenation of ?±,?2-enones to allylic alcohols can be realized by using Noyori's Ru bifunctional system, the selective reduction of the C=C bonds in ?±,?2-enones without touching the C=O bonds still lacks a general, simple, and efficient procedure. Ruthenium-catalyzed conjugate hydrogenation of various ?±,?2-enones to saturated ketones with high selectivity was investigated. The most important feature of this procedure was that hydrogen in situ generated from paraformaldehyde (or formalin) and water was employed as the reductant.

Catalytic asymmetric hydrogenation using a [2.2]paracyclophane based chiral 1,2,3-triazol-5-ylidene-Pd complex under ambient conditions and 1 atmosphere of H2

Chiral 1,2,3-triazol-5-ylidene-Pd complexes with the planar chiral [2.2]paracyclophane wing tip group have been synthesized and structurally characterized. The complex with a labile acetonitrile co-ligand is an excellent catalyst for chemoselective hydrogenation of alkynes and alkenes and enantioselective hydrogenation of prochiral alkenes at ambient conditions and 1.0 atmosphere of H2.

[Copper(phenanthroline)(bisisonitrile)]+-Complexes for the Visible-Light-Mediated Atom Transfer Radical Addition and Allylation Reactions

A series of heteroleptic [Cu(phenantroline)(bisisonitrile)]+-complexes was synthesized, and their structural, spectroscopic, and electrochemical properties were investigated. The new copper(I) complexes were employed as photoredox-catalysts in the visible-light-mediated atom transfer radical addition (ATRA). Especially, [Cu(dpp)(binc)]BF4 (6a-BF4)(dpp = 2,9-diphenyl-1,10-phenanthroline; binc = bis(2-isocyanophenyl) phenylphosphonate) proved to be highly active owing to an enhanced excited-state lifetime compared to the commonly employed [Cu(dap)2]Cl (1-Cl)(dap = 2,9-di(p-anisyl)-1,10-phenanthroline). Furthermore, the catalyst could be applied to allylation reactions with trimethylallylsilane under mild visible-light photoredox conditions.

A novel transition metal-free conjugate reduction of α,β-unsaturated ketones with tosylhydrazine as a hydrogen source

A novel and efficient method has been developed for the chemoselective conjugate reduction of α,β-unsaturated ketones with tosylhydrazine as a hydrogen source to the corresponding saturated ketones in moderate to good yields. The present protocol does not require the use of transition metal, and is efficient being applicable to a wide range of substrates (25 examples).