21856-94-0

Basic information

• Product Name: Bis(4-methylphenyl) perselenide
• Synonyms: Bis(4-methylphenyl) perdiselenide;Bis(4-methylphenyl) perselenide;Di(4-methylphenyl) perselenide;Di(p-tolyl) perselenide;p-Tolyl diselenide
• CAS NO: 21856-94-0
• Molecular Formula: C₁₄H₁₄Se₂
• Molecular Weight: 340.18
• Mol File: 21856-94-0.mol

Chemical Properties

• Melting Point: 46 °C
• Boiling Point: 398.8±45.0 °C(Predicted)
• Appearance: /
• CAS DataBase Reference: Bis(4-methylphenyl) perselenide(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(4-methylphenyl) perselenide(21856-94-0)
• EPA Substance Registry System: Bis(4-methylphenyl) perselenide(21856-94-0)

Safety Data

• Hazardous Substances Data: 21856-94-0(Hazardous Substances Data)

Upstream product

• 21856-93-9 p-tolyl selenocyanate 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 49609-84-9 2-Chloronicotinoyl chloride 
• 37849-35-7 NaSe-p-CH3C6H4 
• 62029-64-5 4-methylphenyl ester of 2-chloro-selenonicotin acid 
• 624-31-7 4-tolyl iodide 
• 56504-42-8 bis(phenylsulfonyl) diselenide 
• 6729-64-2 tri(p-tolyl)bismuth dichloride 
• 106-38-7 para-bromotoluene 
• 5720-05-8 4-methylphenylboronic acid 
• 65935-86-6 2-Methylsulfanyl-selenobenzoic acid Se-p-tolyl ester 
• 57573-52-1 4-methylbenzene diazonium 
• 62247-15-8 Se-(4-methylphenyl) benzenecarboselenoate 
• 73831-79-5 2-(4-methylphenylseleno)-selenonicotinacid-Se-4-methylphenylester 

Downstream Products

• 83859-32-9 4-tolyl phenyl selenide 
• 37773-23-2 p-Selenocresol 
• 20753-52-0 toluene-4-seleninic acid 
• 62350-88-3 tribromo-p-tolyl-λ⁴-selane 
• 56717-54-5 2-Chloraethyl-4'-tolylseleniddichlorid 
• 20343-91-3 bis(p-tolylseleno)methane 
• 37773-35-6 methyl p-tolylselenide 
• 202332-61-4 mono<6-(p-tolylseleno)-6-deoxy>-β-cyclodextrin 
• 210708-02-4 1-Chloromethylselanyl-4-methyl-benzene 
• 154927-56-7 4-chlorophenyl 4’-methylphenyl selenide 

Relevant articles and documents

Selenium and Tellurium Derivatives of Corannulene: Serendipitous Discovery of a One-Dimensional Stereoregular Coordination Polymer Crystal Based on Te-O Backbone and Side-Chain Aromatic Array

Monobromo-, tetrabromo-, and pentachloro-corannulene are subjected to nucleophilic substitution reactions with tolyl selenide and phenyl telluride-based nucleophiles generated in situ from the corresponding dichalcogenides. In the case of selenium nucleophile, the reaction provides moderate yields (52–77 %) of the targeted corannulene selenoethers. A subsequent oxidation of the selenium atoms proceeds smoothly to furnish corannulene selenones in 81–93 % yield. In the case of tellurides, only monosubstitution of the corannulene scaffold could be achieved albeit with concomitant oxidation of the tellerium atom. Unexpectedly, this monotelluroxide derivative of corannulene (RR'Te=O, R=Ph, R’=corannulene) is observed to form a linear coordination polymer chain in the crystalline state. In this chain, Te-O constitutes the polymer backbone around which the aromatic groups (R and R’) arrange as polymer side-chains. The polymer crystal is stabilized through intramolecular π–π stacking interactions of the side-chains and intermolecular hydrogen and halogen bonding interactions with the solvent (chloroform) molecules. Interestingly, each diad of the polymer chain is racemic. Therefore, in terms of stereoregularity, the polymer chain can be described as syndiotactic.

ORGANISCHE PHOTOCHEMIE. XL. SELENOBENZOSELENINE, NEUE RINGSYSTEME DURCH SELENOLESTER-SELENINON-TRANSFORMATIONEN

The two new ring systems 9H-selenolobenzoselenine and 4H-selenolobenzoselenine are described; these compounds are synthesized by photoinduced selenol ester-seleninone transformations of Se-p-tolylselenophenselenocarboxylates.

Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source

A new catalytic protocol for the synthesis of selenoesters from aryl iodides and diaryl diselenides has been developed, where formic acid was employed as an efficient, low-cost, and safe substitute for toxic and gaseous CO. This protocol presents a high functional group tolerance, providing access to a large family of selenoesters in high yields (up to 97%) while operating under mild reaction conditions, and avoids the use of selenol which is difficult to manipulate, easily oxidizes, and has a bad odor. Additionally, this method can be efficiently extended to the synthesis of thioesters with moderate-to-excellent yields, by employing for the first time diorganyl disulfides as precursors.

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.).

Green preparation method of aryl diselenium ether type organic selenium compound

The invention discloses an aryl diselenium ether compound synthesis method. The synthesis method comprises the following steps: taking the compound represented by the formula (I) as a reaction raw material, CuBr as a catalyst, KOH in the condition Se, a reducing agent, a disproportionation reaction, water or ethanol as a solvent, and 60 °C. After completion of the reaction, the obtained reaction solution is subjected to post-treatment (if ethanol is recovered as solvent) to obtain the aryl diselenoether compound represented by the formula (II), the yield is close 100%, the subsequent treatment is simple, and a complex separation and purification method is not needed to obtain a pure product. The solvent is recovered as a solvent such as ethanol. , It is preferable. The method is more green. Economy, high efficiency, environmental protection.

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.

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.

Visible-light-driven radical 1,3-addition of selenosulfonates to vinyldiazo compounds

Herein, we report a visible-light-driven radical 1,3-selenosulfonylation of vinyldiazo compounds with selenosulfonates, providing various γ-seleno allylic sulfones in good yields. This photochemical reaction was carried out at room temperature in an open flask using ethyl acetate as the solvent without any photocatalysts or additives. The control experiments corroborated that the 1,3-addition proceeded via a radical-chain propagation process. The synthetic applications of the resulting products were demonstrated by deselenization, reduction, bromination and allylation.

Size and Quality Enhancement of 2D Semiconducting Metal-Organic Chalcogenolates by Amine Addition

The use of two-dimensional (2D) materials in next-generation technologies is often limited by small lateral size and/or crystal defects. Here, we introduce a simple chemical strategy to improve the size and overall quality of 2D metal-organic chalcogenolates (MOCs), a new class of hybrid organic-inorganic 2D semiconductors that can exhibit in-plane anisotropy and blue luminescence. By inducing the formation of silver-amine complexes during a solution growth method, we increase the average size of silver phenylselenolate (AgSePh) microcrystals from 1 mm, while simultaneously extending the photoluminescence lifetime and suppressing mid-gap emission. Mechanistic studies using 77Se NMR suggest dual roles for the amine in promoting the formation of a key reactive intermediate and slowing down the final conversion to AgSePh. Finally, we show that amine addition is generalizable to the synthesis of other 2D MOCs, as demonstrated by the growth of single crystals of silver 4-methylphenylselenolate (AgSePhMe), a novel member of the 2D MOC family.