88372-92-3

Usage

Uses

Used in Agricultural Industry:
1,2-bis(4-chlorophenyl) ethane-1,2-dione is used as an acaricide for controlling mites on various crops such as cotton, fruits, and vegetables. Its application is aimed at protecting these crops from mite infestations, which can lead to significant yield losses and affect the quality of the produce.
However, due to concerns regarding its potential health and environmental effects, dicofol has faced regulatory actions. Studies have associated it with reproductive and developmental toxicity, and it is considered a possible carcinogen. As a result, its use has been banned or heavily restricted in several countries, reflecting the need for safer alternatives in agricultural pest control.

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 
• 1820-42-4 bis(4-chlorophenyl)acetylene 
• 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 
• 79183-98-5 1,2-dibromo-1,2-di-(p-chlorophenyl)-ethane 
• 4231-70-3 p-chlorobenzoyl-1H-1,2,3-benzotriazole 
• 201230-82-2 carbon monoxide 

Downstream Products

• 2216-49-1 triphenylmethyl radical 
• 4254-20-0 4,4'-dichlorobenzoin 
• 1309776-09-7 C₃₁H₂₂Cl₂N₂O₃ 
• 23102-08-1 2-(4-Chlor-benzoyl)-2-(4-chlor-phenyl)-1.1-dicyanaethylen 
• 811436-88-1 5,6-bis(4-chlorophenyl)-3-(tert-butoxycarbonyl)-pyrazine-2-carboxylic acid 
• 810685-52-0 5,6-bis(4-chlorophenyl)-N-piperidin-1-yl-3-(piperidin-1-ylcarbonyl)pyrazine-2-carboxamide 
• 810685-51-9 5,6-bis(4-chlorophenyl)-3-(piperidin-1-ylcarbonyl)pyrazine-2-carboxylic acid 
• 95026-92-9 2,3-bis(4-chlorophenyl)-5-phenylfuran 

Relevant academic research and scientific papers

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.

Aerobic oxidation of alcohols catalyzed by in situ generated gold nanoparticles inside the channels of periodic mesoporous organosilica with ionic liquid framework

In situ generated gold nanoparticles inside the nanospaces of periodic mesoporous organosilica with an imidazolium framework (Au?PMO-IL) were found to be highly active, selective, and reusable catalysts for the aerobic oxidation of activated and nonactivated alcohols under mild reaction conditions. The catalyst was characterized by nitrogen adsorption-desorption measurement, thermogravimetric analysis (TGA), transmission electron microscopy (TEM), elemental analysis (EA), diffuse reflectance infrared Fourier transform spectroscopy (DRIFT), X-ray photoelectron spectroscopy (XPS), and inductively coupled plasma atomic emission spectroscopy (ICP-AES). The catalyst exhibited excellent catalytic activity in the presence of either Cs2CO3 (35 °C) or K2CO3 (60 °C) as reaction bases in toluene as a reaction solvent. Under both reaction conditions, various types of alcohols (up to 35 examples) including activated benzylic, primary and secondary aliphatic, heterocyclic, and challenging cyclic aliphatic alcohols converted to the expected carbonyl compounds in good to excellent yields and selectivity. The catalyst was also recovered and reused for at least seven reaction cycles. Data from three independent leaching tests indicated that amounts of leached gold particles were negligible (0.2 ppm). It is believed that the combination of bridged imidazolium groups and confined nanospaces of PMO-IL might be a major reason explaining the remarkable stabilization and homogeneous distribution of in situ generated gold nanoparticles, thus resulting in the highly active and recyclable catalyst system.

Substituent Effect in the Synthesis of α,α-Dibromoketones, 1,2-Dibromalkenes, and 1,2-Diketones from the Reaction of Alkynes and Dibromoisocyanuric Acid

Internal alkynes reacted with dibromoisocyanuric acid/H2O to afford α,α-dibromoketone and 1,2-diketone derivatives. Diarylalkynes with activating groups provided 1,2-diketone derivatives as the major products, whereas diarylalkynes with a non-activating group or alkylarylalkynes gave α,α-dibromoketone derivatives as the major products. In addition, diarylalkynes with deactivating groups provided 1,2-dibromoalkenes. The reaction was conducted at room temperature and showed good yields in most cases. Reaction pathways have been proposed on the basis of experimental observations and density functional theory (DFT) calculations. (Figure presented.).

B2pin2-mediated copper-catalyzed oxidation of alkynes into 1,2-diketones using molecular oxygen

An intriguing aerobic oxidation of alkynes through copper catalysis is described, in which bis(pinacolato)diboron (B2pin2) played a dominant intermediary role in the formation 1,2-diketones. This novel protocol, which can be performed at room temperature, is versatile for various substituted alkynes, including diarylalkynes and arylalkylalkynes. The mechanism of this reaction was preliminarily investigated by control experiments.

Ring Closing Metathesis Approach for the Synthesis of o-Terphenyl Derivatives

A linear synthesis of o-terphenyl derivatives has been delineated using ring closing metathesis (RCM) as the key step. In this approach, benzil derivatives upon allyl Grignard addition provides diphenyl-1,2-diallyl dihydroxy derivatives which undergo ring closing metathesis to afford tetrahydro terphenyl derivatives. Aromatization-driven dehydration then leads to a diverse set of electron rich and electron deficient o-terphenyls. Furthermore, oxidative coupling of electron rich o-terphenyls provides the corresponding triphenylene derivatives.

Computer-aided studies for novel arylhydantoin 1,3,5-triazine derivatives as 5-HT6 serotonin receptor ligands with antidepressive-like, anxiolytic and antiobesity action in vivo

This study focuses on the design, synthesis, biological evaluation, and computer-aided structure-activity relationship (SAR) analysis for a novel group of aromatic triazine-methylpiperazines,with an hydantoin spacer between 1,3,5-traizine and the aromatic fragment. New compounds were synthesized and their affinities for serotonin 5-HT6, 5-HT1A, 5-HT2A, 5-HT7, and dopamineD2 receptorswere evaluated. The induced-fit docking (IFD) procedure was performed to explore the 5-HT6 receptor conformation space employing two lead structures. It resulted in a consistent binding mode with the activity data. For the most active compounds found in each modification line, anti-obesity and anti-depressive-like activity in vivo, as well as "druglikeness" in vitro, were examined. Two 2-naphthyl compounds (18 and 26) were identified as themost active 5-HT6R agents within each leadmodification line, respectively. The 5-(2-naphthyl)hydantoin derivative 26, themost active one in the series (5-HT6R: Ki = 87 nM), displayed also significant selectivity towards competitive G-protein coupled receptors (6-197-fold). Docking studies indicated that the hydantoin ring is stabilized by hydrogen bonding, but due to its different orientation, the hydrogen bonds formwith S5.44 and N6.55 or Q6.58 for 18 and 26, respectively. Compound 26 exerted anxiolytic-like and antidepressant-like activities. Importantly, it demonstrated anti-obesity properties in animals fed palatable feed, and did not show toxic effects in vitro.