20541-49-5

Usage

Chemical Properties

Yellow crystalline powder

InChI:InChI=1/C12H8Cl2Se2/c13-9-1-5-11(6-2-9)15-16-12-7-3-10(14)4-8-12/h1-8H

Upstream product

• 20753-53-1 4-chlorobenzeneseleninic acid 
• 42572-42-9 phenylselenium trichloride 
• 57878-20-3 p-chlorobenzeneselenenyl chloride 
• 856129-18-5 ethyl-dichloro-(4-chloro-phenyl)-λ⁴-selane 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 106-39-8 bromochlorobenzene 
• 34713-70-7 2-Phenylpropanal 
• 60805-87-0 p-chlorobenzeneselenenyl bromide 
• 63126-47-6 (2S)-2-(methoxymethyl)-1-pyrrolidine 
• 50630-24-5 β-(phenylseleno)ethyl chloride 
• 16645-10-6 p-chloroselenophenol 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 7452-29-1 sodium O,O-diethyl phosphoroselenoate 

Downstream Products

• 20753-53-1 4-chlorobenzeneseleninic acid 
• 62635-83-0 p-chorophenylselenium trichloride 
• 53973-66-3 (4-chlorophenyl) dodecyl selenide 
• 82454-06-6 (Z)-2-(4-Chloro-phenylselanyl)-pent-2-enal 
• 82453-98-3 (Z)-2-(4-Chloro-phenylselanyl)-oct-2-enal 
• 147047-90-3 1-Chloro-4-hept-1-ynylselanyl-benzene 
• 115306-02-0 2-<(4-chlorophenyl)seleno>-1,3-dithiane 
• 101220-65-9 1-Chloro-4-difluoromethylselanyl-benzene 
• 82454-01-1 (Z)-4-(4-Chloro-phenylselanyl)-non-3-en-5-one 
• 82454-03-3 2-(4-Chloro-phenylselanyl)-3-methyl-1-phenyl-but-2-en-1-one 
• 74061-09-9 N-p-chlorobenzoyl-p-chlorobenzeneseleninimidoyl chloride 
• 60805-72-3 C₁₂H₉ClO₂SSe 
• 132591-63-0 6-(4-Chloro-phenylselanylmethyl)-1,4-dioxa-spiro[4.4]nonane 
• 145215-54-9 (+/-)-syn-2-[2-(4-chlorophenylselanyl)ethyl]-3-methyl-pent-4-ynoic acid 

Relevant academic research and scientific papers

Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor-Acceptor Complex and a Reversible Adsorption to Solid Support Strategy

DNA-encoded library (DEL) technology is a powerful tool in the discovery of bioactive probe molecules and drug leads. Mostly, the success in DEL technology stems from the molecular diversity of the chemical libraries. However, the construction of DELs has been restricted by the idiosyncratic needs and the required low concentration (～1 mM or less) of the library intermediate. Here, we report visible-light-promoted on-DNA radical coupling reactions via an electron donor-acceptor (EDA) complex and a reversible adsorption to solid support (RASS) strategy. This protocol provides a unique solution to the challenges of increasing the reactivity of highly diluted DNA substrates and reducing the residues of heavy metals from photocatalysts. A series of on-DNA indole sulfone and selenide derivatives were obtained with good to quantitative conversions. It is anticipated that these mild-condition on-DNA radical reactions will significantly improve the chemical diversity of DELs and find widespread utility to DEL construction.

Synthesis of Seleno Oxindoles via Electrochemical Cyclization of N-arylacrylamides with Diorganyl Diselenides

The tandem cyclization of acrylamide with diselenides facilitated by electrochemical oxidation was successfully developed. This strategy provided an environmentally friendly method for the construction of C?Se bond. A series of seleno oxindoles with pharmacological activity were obtained by using this well-designed tandem cyclization strategy. The in vitro antitumor activity of the compounds was also screened through MTT assay. Results showed that the seleno oxindoles exhibited better antitumor activity than other oxindole derivatives. (Figure presented.).

Clarification on the reactivity of diaryl diselenides toward hexacyclohexyldilead under light

In this study, the reactivity of organochalcogen compounds toward a representative alkyl-lead bond compound under light was investigated in detail. Under light irradiation, the Cy-Pb bond of Cy6 Pb2 (Cy = cyclohexyl) undergoes homolytic cleavage to generate a cyclohexyl radical (Cy?). This radical can be successfully captured by diphenyl diselenide, which exhibits excellent carbon-radical-capturing ability. In the case of (PhS)2 and (PhTe)2, the yields of the corresponding cyclohexyl sulfides and tellurides were lower than that of (PhSe)2. This probably occurred due to the low carbon-radical-capturing ability of (PhS)2 and the high photosensitivity of the cyclohexyl-tellurium bond.

Visible Light-Promoted Selenylation/Cyclization of Enaminones toward the Formation of 3-Selanyl-4H-Chromen-4-Ones

A simple and efficient visible-light-promoted selenylation/cyclization of enaminones have been realized for the practical synthesis of 3-selanyl-4H-chromen-4-ones. This reaction is performed in the mild conditions, no transition metal catalyst or photocatalysts and no additional oxidants are required. In addition, the 3-selanyl-4H-chromen-4-ones could be easily converted to selanyl-functionalized pyrimidines by reacting with benzamidine substrates. (Figure presented.).

Blue light-promoted radical sulfoximido-chalcogenization of aliphatic and aromatic alkenes

A transition metal-free synthesis ofN-(arylthio/seleno)ethyl sulfoxidminesviablue light-promoted radical sulfoximido-chalcogenization of aliphatic and aromatic alkenes was developed. The sulfoximidation process demonstrated high chemoselectivity and allowed a broad substrate scope, completing the sulfoximido-chalcogenization of alkenes in good yields.

Highly selective radical isothiocyano-chalcogenization of alkenes with NH4SCN in water

In the presence of catalytic amounts of molecular iodine and stoichiometric potassium persulfate, a green, highly chemoselective, regioselective and cis-selective radical isothiocyano-chalcogenization of alkenes with NH4SCN in water is disclosed. This three component reaction features high selectivities, an environmentally benign process, mild conditions, high yields, excellent functional-group tolerance, and broad substrate scope. The resulting products can be further transformed into other molecules with structural similarities of these compounds to bioactive analogs.

Preparation of selenofunctionalized heterocycles via iodosobenzene-mediated intramolecular selenocyclizations of olefins with diselenides

An intramolecular selenocyclizations of olefins mediated by a commercially available hypervalent iodine(III) reagent, PhIO, was developed. This method provided access to a wide range of selenenylated heterocycles under ambient conditions. The striking advantages of this protocol over all previous methods include mild reaction conditions, easy operation, good yields, high levels of functional group compatibility, large–scale application and suitability for the late-stage functionalization of complex molecules of biological importance.

Metal-free synthesis of unsymmetrical selenides from pyridinium salts and diselenides catalysed by visible light

We report the first metal-free selenolations of pyridinium salts with diselenides to prepare unsymmetrical organoselenides catalysed by visible light. This protocol is an efficient and green method for the preparation of unsymmetrical organoselenides because metal-free conditions and readily accessible diselenides are used.

FeCl3-catalyzed three-component aryl-selenylation of alkenes

FeCl3-catalyzed three-component aryl-selenylation of alkenes with good to excellent yields has been disclosed. This method is characterized by synthesis of complicated products in a single-step reaction, simple operation and readily available commercially reagents. Finally, a reasonable mechanism of FeCl3-catalyzed aryl-selenylation is proposed.

Iodine mediated synthesis of diaryl diselenides using SeO2 as a selenium source

A simple, eco-friendly and convenient procedure has been developed for the synthesis of diphenyl diselinides from readily available aryl boronic acids by reaction with SeO2 in the presence of iodine under simple conditions. The methodology is reported about 19 examples and applicable to a broad scope of aryl boronic acids containing electron-rich and electron-poor substituents. Apart from being milder and environmentally benign conditions, this synthetic protocol comprises a novel, reliable methodology to give good to high yields of the desired diaryl diselenides.