3457-46-3

Usage

Chemical Properties

White Crystal

InChI:InChI=1/C14H8Cl2O2/c15-11-5-1-9(2-6-11)13(17)14(18)10-3-7-12(16)8-4-10/h1-8H

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 4254-20-0 4,4'-dichlorobenzoin 
• 4137-78-4 4,α,α,4',α',α'-hexachloro-bibenzyl 
• 64-19-7 acetic acid 
• 860537-22-0 2-(N-ethyl-p-toluidino)-1-(4-chloro-phenyl)-ethanone 
• 622-57-1 N-ethyl-p-tolylamine 
• 18164-50-6 2,2-bis(4-chlorophenyl)acetaldehyde 
• 14774-78-8 4-chlorophenyl lithium 
• 106675-70-1 N¹,N²-dimethoxy-N¹,N²-dimethyloxalamide 
• 67-56-1 methanol 
• 873-76-7 para-Chlorobenzyl alcohol 
• 122-01-0 4-chloro-benzoyl chloride 
• 33599-26-7 α-(4-Chlorophenyl)-4-morpholineacetonitrile 
• 51490-05-2 1,2-bis(4-chlorophenyl)ethanone 

Downstream Products

• 30454-83-2 5,5-bis(4-chlorophenyl)-3-methyl-2-thioxoimidazolidin-4-one 
• 7213-62-9 4,5-Di-(4-chlorphenyl)-acenaphtho<1.2-j>fluoranthen 
• 92030-44-9 4,4'-dichloro-3,3'-dinitro-benzil 
• 37580-81-7 1,2-bis(4-chlorophenyl)-1,2-ethandiol 
• 104-88-1 4-chlorobenzaldehyde 
• 548760-13-0 5,6-bis(4-chlorophenyl)-pyrazine-2-carboxylic acid 
• 94147-84-9 1,2-Bis-(4-chloro-phenyl)-2-hydroxy-3-imidazol-1-yl-propan-1-one 
• 107680-28-4 (2R,3S)-2,3-Bis-(4-chloro-phenyl)-1-imidazol-1-yl-butane-2,3-diol 

Relevant academic research and scientific papers

Microwave-assisted solvent-free catalyzed synthesis and luminescence properties of 1,2,4,5-tetrasubstituted imidazoles bearing a 4-aminophenyl substituent

A solvent-free microwave-assisted four-component synthesis of 1,2,4,5-tetrasubstituted imidazoles bearing a 4-aminophenyl substituent was studied by condensation of p-phenylenediamine, aryl diketone, benzaldehyde derivatives and ammonium acetate in the presence of solid support silica gel and catalyst Keggin-H3[PW12O40]. The effects of four components molar ratio along with catalyst loading, irradiation time on the yields were investigated. Also, the structures of synthesized compounds were characterized by FT-IR, HRMS, 1H NMR and 13C NMR spectroscopy. Furthermore, their ultraviolet-visible maximum absorption, liquid fluorescence emission maximum and quantum yields were, respectively, measured in 0.05 M H2SO4 aqueous solution and in dichloromethane. Simultaneously, solid fluorescence spectra were determined in the powder state. The relationships between the optical behavior and the polarity of the solvents for some compounds were assessed. The results showed that the fluorescence quantum efficiency was increased by introducing amino phenyl in comparison with benzyl on 1-position of trisubstitued imidazoles. The compounds synthesized were sensitive to the polarity of the solvents.

Kinetics and mechanism of benzoin oxidation using iron(III) in the presence of ferrozine or 2,2′-bipyridine in acidic medium

Kinetics and mechanism of oxidation of benzoin (H2B) by ferrozine (Fz) or 2,2′-bipyridine (bipy) have been carried out in aqueous HNO3 medium. The rate shows first-order dependence on [H 2B] and [Fe3+| and inverse second-order dependence on (H+). The rate of reaction increased with increase in the ligand concentration. The increase in dielectric constant will increase the rate, while increase in [HNO3] decreased it. Substituent and temperature effects on the rates have been investigated. The rate laws derived are in excellent agreement with the experimental results. Plausible mechanisms are suggested.

OXIDATIVE TRAPPING OF TRANSIENT THIAZOLIUM-ALDEHYDE ADDUCTS BY INTRAMOLECULAR FLAVIN. FLAVIN-THIAMINE BISCOENZYME MODEL

A biscoenzime which has within a molecular structure both flavin and thiazolium ion was synthesized.In the presence of the biscoenzyme and hexadecyltrimethylammonium bromide (CTAB) micelle, aldehydes were efficiently converted to carboxylic acids and the acyloin condensation products were scarcely detected. Thus, the biscoenzyme serves as an interesting model system for pyruvate dehydrogenase.

Coenzyme Models. 31. Efficient Trapping of Transient Thiazolium-Aldehyde Adducts (Active Aldehydes) by Intramolecular and Quasi-Intramolecular Flavins.Flavin-Thiamin Biscoenzyme

The reaction sequence of acyloin condensation of aldehydes, catalyzed by thiazolium ion bound to the CTAB micelle, can be diverted by the addition of flavin to the oxidation reaction to afford the corresponding carboxylic acids.It was found, however, that when the aldehyde concentration is elevated or the aldehyde is relatively reactive, intermolecular flavin (3-methyltetra-O-acetylriboflavin, MeFl) cannot trap the intermediates (active aldehydes) formed from thiazolium ion and aldehydes completely, leading to a competition between the conventional acyloin condensation and the flavin oxidation.We have applied the concept of intramolecular catalysis to the system by two methods in order to suppress the acyloin condensation relative to the flavin oxidation.The first utilizes quasi-intramolecular flavin oxidation in which hydrophobic 10-dodecylisoalloxazine (10-DodFl) and N-hexadecylthiazolium bromide (HxdT) are bound to a CTAB micelle aggregate.The second is a flavin-thiazolium biscoenzyme (Fl-T) oxidation in which the intermediates on the thiazolium moiety are oxidized efficiently by the intramolecular flavin.When 4-chlorobenzaldehyde (100mM) was employed as substrate, the trapping efficiency (=flavinoxidation product/sum of acyloin condensation products) for MeFl was 1.6.The trapping efficiency for the quasi-intramolecular flavin oxidation was improved up to 15-33-fold owing to the enhanced local concentration of 10-DodFl in the micelle phase; efficiency for the biscoenzyme system was further enhanced (>115-fold).A kinetic examination has established that the reaction is zero order in MeFl for the intermolecular flavin oxidation of 4-chlorobenzaldehyde, whereas it becomes first order in MeFl for the oxidation of more reactive pyridine-4-carboxaldehyde (pyCHO).This indicates that the rate-limiting step changes depending on the reactivity of aldehyde: the deprotonation from the thiazolium-aldehyde adduct is the limiting in the oxidation of 4-chlorobenzaldehyde, whereas the oxidation of the deprotonated active aldehyde by MeFl becomes rate limiting in the oxidation of pyCHO.On the other hand, quasi-intramolecular flavin oxidation of pyCHO was zero order in 10-DodFl at low pyCHO concentrations (50mM).In the biscoenzyme oxidation of pyCHO, the zero-order decrease was always observed for up to 60percent reaction, indicating the high efficiency of intramolecular flavin as a trapping agent.The present system is a relevant model for pyruvate oxidase which requires FAD and thiamine pyrophosphate as cofactors and catalyzes the convernion of pyruvic acid to acetic acid.

FACILE OXIDATION OF ALDEHYDES AND α-KETO ACIDS AS CATALYZED BY FLAVIN AND THIAZOLIUM ION

Oxidation of aldehydes and α-keto acids to carboxylic acids occurs readily in the presence of a flavin, thiazolium ion, and cationic micelles, the reaction involving trapping by the flavin of the intermediate formed from the substrate-thiazolium adducts through deprotonation or decarboxylation.

Synthesis of 1,2-diketones by mercury-catalyzed alkyne oxidation

The first mercury-catalyzed synthesis of 1,2-diketones by alkyne oxidation has been developed. This inexpensive method extends the potential of mercury catalysis and allows the rapid construction of various 1,2-diketones and α-carbonyl amides in good yields with high functional group tolerance.

Catalyst-Free and Transition-Metal-Free Approach to 1,2-Diketones via Aerobic Alkyne Oxidation

A catalyst-free and transition-metal-free method for the synthesis of 1,2-diketones from aerobic alkyne oxidation was reported. The oxidation of various internal alkynes, especially more challenging aryl-alkyl acetylenes, proceeded smoothly with inexpensive, easily handled, and commercially available potassium persulfate and an ambient air balloon, achieving the corresponding 1,2-diketones with up to 85% yields. Meanwhile, mechanistic studies indicated a radical process, and the two oxygen atoms in the 1,2-diketons were most likely from persulfate salts and molecular oxygen, respectively, rather than water.

One-pot cascade synthesis of α-diketones from aldehydes and ketones in water by using a bifunctional iron nanocomposite catalyst

A new methodology for the synthesis of α-diketones was reportedviaa one-pot cascade process from aldehydes and ketones catalyzed by a bifunctional iron nanocomposite using H2O2as a green oxidant in water. The one-pot strategy showed excellent catalytic stability, comprehensive suitability of substrates and important practical utility for directly synthesizing biologically active and medicinally valuable N-heterocyclesviaan intermittent process.

1-butyl-3-methylimidazol-2-ylidene as an efficient catalyst for cross-coupling between aromatic aldehydes and N-aroylbenzotriazoles

Cross-coupling of aromatic aldehydes with N-aroylbenzotriazoles in [Bmim]Br in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) provided an efficient procedure for the synthesis of 1,2-diarylethane-1,2-diones.

Conversion of alkynes into 1,2-diketones using HFIP as sacrificial hydrogen donor and DMSO as dihydroxylating agent

A metal-free and hypervalent iodine free conversion of internal alkynes into 1,2-diketo compounds has been described. The efficacy of the present protocol rely on the use of HFIP (1,1,1,3,3,3-Hexafluoro-2-propanol) as reducing agent of alkynes and DMSO as dihydroxylating agent of olefins to acquire the desired chemical transformations. The obtained 1,2-diketones were further transformed into useful derivatives.