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Chloranil

Base Information Edit
  • Chemical Name:Chloranil
  • CAS No.:118-75-2
  • Deprecated CAS:142655-99-0,856302-53-9,856302-53-9
  • Molecular Formula:C6Cl4O2
  • Molecular Weight:245.877
  • Hs Code.:29147090
  • European Community (EC) Number:204-274-4
  • ICSC Number:0780
  • NSC Number:8432
  • UNII:01W5X7N5XV
  • DSSTox Substance ID:DTXSID2020266
  • Nikkaji Number:J5.304J
  • Wikipedia:Chloranil
  • Wikidata:Q629632
  • Pharos Ligand ID:Z5DRS12S6CCZ
  • Metabolomics Workbench ID:55466
  • ChEMBL ID:CHEMBL192627
  • Mol file:118-75-2.mol
Chloranil

Synonyms:2,3,5,6-Tetrachloro-1,4-benzoquinone;Chloranil;Coversan;Reranil;Spergon;Tetrachloro 1,4 benzoquinone;Tetrachloro-1,4-benzoquinone;Vulklor

Suppliers and Price of Chloranil
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Tetrachloro-1,4-benzoquinone
  • 100g
  • $ 110.00
  • TCI Chemical
  • Chloranil (ca. 2% in N,N-Dimethylformamide) [for Detection of Primary and Secondary Amines]
  • 10ML
  • $ 45.00
  • TCI Chemical
  • Chloranil >98.0%(GC)(T)
  • 500g
  • $ 127.00
  • TCI Chemical
  • Chloranil >98.0%(GC)(T)
  • 25g
  • $ 25.00
  • SynQuest Laboratories
  • Tetrachloro-1,4-benzoquinone
  • 25 g
  • $ 16.00
  • SynQuest Laboratories
  • Tetrachloro-1,4-benzoquinone
  • 100 g
  • $ 36.00
  • Sigma-Aldrich
  • Tetrachloro-1,4-benzoquinone 99%
  • 100g
  • $ 158.00
  • Sigma-Aldrich
  • p-Chloranil for synthesis. CAS 118-75-2, pH 3.5 - 4.5 (100 g/l, H O, 20 °C) (slurry)., for synthesis
  • 8023610250
  • $ 64.70
  • Sigma-Aldrich
  • p-Chloranil for synthesis
  • 250 g
  • $ 61.97
  • Sigma-Aldrich
  • Tetrachloro-1,4-benzoquinone 99%
  • 25g
  • $ 59.90
Total 177 raw suppliers
Chemical Property of Chloranil Edit
Chemical Property:
  • Appearance/Colour:Golden crystals 
  • Vapor Pressure:1 hPa (71 °C) 
  • Melting Point:295-296 ºC (dec.) 
  • Boiling Point:269.5 ºC at 760 mmHg 
  • Flash Point:111.7 ºC 
  • PSA:34.14000 
  • Density:1.8 g/cm3 
  • LogP:2.51660 
  • Storage Temp.:Store below +30°C. 
  • Solubility.:0.25g/l practically insoluble 
  • Water Solubility.:insoluble 
  • XLogP3:3.4
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:2
  • Rotatable Bond Count:0
  • Exact Mass:245.862290
  • Heavy Atom Count:12
  • Complexity:278
Purity/Quality:

98%min *data from raw suppliers

Tetrachloro-1,4-benzoquinone *data from reagent suppliers

Safty Information:
  • Pictogram(s): IrritantXi,DangerousN,HarmfulXn 
  • Hazard Codes:Xi,N,Xn 
  • Statements: 36/38-50/53-20 
  • Safety Statements: 37-60-61-22 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Other Classes -> Aromatic Ketones, Halogenated
  • Canonical SMILES:C1(=C(C(=O)C(=C(C1=O)Cl)Cl)Cl)Cl
  • Inhalation Risk:Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
  • Effects of Short Term Exposure:The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the central nervous system. Exposure at high levels could cause unconsciousness.
  • General Description Chloranil (2,3,5,6-tetrachloro-1,4-benzoquinone) is a versatile oxidizing agent widely used in organic synthesis, including the preparation of carbazoles via silver-copper co-catalyzed cascade reactions, the synthesis of BODIPY-based semiconductors, and the antimicrobial evaluation of heterocyclic amines. It also serves as a key reagent in green chemistry approaches, such as ultrasound-initiated thiadiazole formation in water, due to its efficiency in oxidation reactions. Its applications span materials science, medicinal chemistry, and environmentally friendly synthetic methodologies.
Technology Process of Chloranil

There total 376 articles about Chloranil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With ammonium nitrate; trifluoroacetic anhydride; In dichloromethane; at 25 - 30 ℃; for 4h;
DOI:10.1021/jo00328a013
Refernces Edit

Synthesis, CoMFA analysis, and receptor docking of 3,5-diacyl-2,4- dialkylpyridine derivatives as selective A3 adenosine receptor antagonists

10.1021/jm980550w

The research aimed to explore the synthesis, structure-activity relationships, and receptor docking of 3,5-diacyl-2,4-dialkylpyridine derivatives as selective antagonists of the A3 adenosine receptor. The study synthesized various pyridine derivatives, including those with fluoro, hydroxy, and ring-constrained substitutions, and tested their affinities for human and rat A3 adenosine receptors using radioligand binding assays. The study concluded that specific structural modifications, such as the inclusion of fluoro groups at certain positions, could enhance the potency and selectivity of pyridine derivatives as A3 receptor antagonists. The research utilized a range of chemicals in the synthesis process, including various aldehydes, ketones, and esters, as well as reagents like DAST for fluorination and tetrachloroquinone for oxidation.

Silver-copper co-catalyzed cascade intramolecular cyclization/desulfinamide/dehydrogenation: One-pot synthesis of substituted carbazoles

10.1039/c8cc03600d

The research aims to develop an efficient method for synthesizing substituted carbazoles, which are important heterocyclic compounds with applications in materials chemistry and medicine. The study reports a silver and copper co-catalyzed cascade reaction involving intramolecular cyclization, desulfinamide, and dehydrogenation steps. Key chemicals used include various arylamine substrates, chloranil as an oxidizing agent, and different silver and copper catalysts such as AgSbF6 and Cu(OAc)2. The reaction conditions were optimized, and the method demonstrated good functional group tolerance and scalability. The study concludes that this catalytic cascade approach is a straightforward and efficient way to synthesize a wide range of substituted carbazoles with high yields, providing a valuable synthetic route for the construction of these important heterocyclic compounds.

A Solution-Processable meso-Phenyl-BODIPY-Based n-Channel Semiconductor with Enhanced Fluorescence Emission

10.1002/cplu.201900317

The research aims to design, synthesize, and characterize a new acceptor-donor-acceptor (AD-A) semiconductor, BDY-Ph-2T-Ph-BDY, which features a central phenyl-bithiophene-phenyl p-donor and BODIPY p-acceptor end-units. The purpose is to develop a solution-processable n-channel semiconductor with enhanced fluorescence emission for next-generation optoelectronics. The study concludes that BDY-Ph-2T-Ph-BDY exhibits an optical band gap of 2.32 eV, highly stabilized HOMO/LUMO energies (-5.74 eV/-3.42 eV), and a D-A dihedral angle of ~66°. It shows good fluorescence efficiency (FF = 0.30) and n-channel OFET transport characteristics (μe = 0.005 cm2/V·s; Ion/Ioff = 104-105), representing a significant improvement in fluorescence quantum yield compared to previous BODIPY semiconductors. This work demonstrates the potential of BDY-Ph-2T-Ph-BDY for high-performance optoelectronic applications. 4-Bromobenzaldehyde is used as a starting material to introduce the phenyl group into the BODIPY structure. N-Ethylpyrrole acts as a building block for the BODIPY core. P-Chloranil (2,3,5,6-Tetrachloro-1,4-benzoquinone) is used as an oxidizing agent in the synthesis process.

Synthesis and antimicrobial activity of styryl/pyrrolyl/pyrazolyl sulfonylmethyl-1,3,4-oxadiazolyl amines and styryl/pyrrolyl/pyrazolyl sulfonylmethyl-1,3,4-thiadiazolyl amines

10.1016/j.ejmech.2016.06.014

The research focuses on the synthesis and antimicrobial activity of a novel class of mono and bis heterocycles, including styryl, pyrrolyl, and pyrazolyl sulfonylmethyl-1,3,4-oxadiazolyl/thiadiazolyl amines. The study utilizes Z-styrylsulfonylacetic acid as a synthetic intermediate and employs various synthetic methodologies to prepare these compounds. The antimicrobial activity of these synthesized compounds was then evaluated against different bacterial and fungal strains. The reactants used in the synthesis encompass semicarbazide, thiosemicarbazide, POCl3, tosylmethyl isocyanide, sodium hydride, diazomethane, and chloranil, among others. The synthesized compounds were characterized using techniques like infrared (IR) spectroscopy, nuclear magnetic resonance (NMR), high-resolution mass spectrometry, and elemental analysis. The antimicrobial activity was assessed using the agar well diffusion method and broth dilution test to determine the minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and minimum fungicidal concentration (MFC). The findings revealed that mono heterocyclic compounds, particularly 5-(4-chlorostyrylsulfonylmethyl)-1,3,4-thiadiazol-2-amine (5c), exhibited superior antimicrobial activity against certain bacteria and fungi compared to the bis heterocyclic systems.

An Expeditious Ultrasound-Initiated Green Synthesis of 1,2,4-Thiadiazoles in Water

10.1007/s10593-020-02632-5

The research focuses on the development of an efficient, environmentally friendly method for synthesizing 1,2,4-thiadiazole derivatives, which are important heterocyclic compounds with a range of biological activities and therapeutic applications. The study introduces a metal- and catalyst-free protocol that utilizes the combination of water and ultrasound technique to achieve the dimerization of primary thioamide derivatives with chloranil, leading to the formation of 1,2,4-thiadiazoles. The optimized reaction conditions resulted in excellent yields within a short reaction time, demonstrating a significant improvement over traditional methods. The chemicals used in the process include primary thioamide derivatives, chloranil as the oxidizing agent, and water as the solvent, with other solvents like MeCN, THF, EtOH, 1,4-dioxane, CHCl3, CH2Cl2, DCE, and DMSO also tested for comparison. The study concludes that the ultrasound-initiated green synthesis in water is a valuable addition to existing methods for synthesizing substituted 3,5-diaryl-1,2,4-thiadiazoles, offering a rapid and efficient approach.

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