1482-82-2

Basic information

• Product Name: Dibenzyl diselenide
• Synonyms: BENZYL DISELENIDE;DIBENZYL DISELENIDE;1,2-Dibenzyldiselane;Dibenzyldiselenium;Diselenide,bis(phenylmethyl);Dibenzyldiselenide, 99+%;Bis(benzyl) perselenide;Dibenzyl perdiselenide
• CAS NO: 1482-82-2
• Molecular Formula: C₁₄H₁₄Se₂
• Molecular Weight: 340.18
• Product Categories: Pharmaceutical Intermediates;Classes of Metal Compounds;Se (Selenium) Compounds;Semimetal Compounds;Building Blocks;Organic Building Blocks;Selenium Compounds
• Mol File: 1482-82-2.mol
• Article Data: 86

Chemical Properties

• Melting Point: 91-93 °C(lit.)
• Boiling Point: 427.3 °C at 760 mmHg
• Flash Point: 212.2 °C
• Appearance: /solid
• Vapor Pressure: 4.13E-07mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: almost transparency in hot Toluene
• Water Solubility: Soluble in water.
• Sensitive: Air Sensitive
• BRN: 1877745
• CAS DataBase Reference: Dibenzyl diselenide(CAS DataBase Reference)
• NIST Chemistry Reference: Dibenzyl diselenide(1482-82-2)
• EPA Substance Registry System: Dibenzyl diselenide(1482-82-2)

Safety Data

• Hazard Codes: T,N
• Statements: 23/25-33-50/53
• Safety Statements: 20/21-28-45-60-61
• RIDADR: UN 3283 6.1/PG 2
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1482-82-2(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow to Yellow to Orange powder to crystaline.

Uses

Dibenzyl diselenide is used as a source of the PhSe unit in organic synthesis. It is also used to introduce PhSe groups by reaction with a variety of nucleophilic, including enolates, enol silyl ethers, Grignard reagents, organolithium reagents, alkenes and amines.

Preparation

Dibenzyl diselenide was synthesized from bis(methoxymagnesium) diselenide reagent as reported by Gunther using benzyl chloride (6.3 g, 0.05 mole) and a methanolic solution of bis(methoxymagnesium) diselenide reagent (from 0.05 gatom of selenium). After 10 min stirring, water (100 mL) and concentrated hydrochloric acid (5 mL) were added, the solution was cooled, and the black solid was collected by filtration. This black solid was then extracted with ethanol to yield a bright yellow solution which, upon solvent removal, gave a yellow crystalline product. The 1H NMR of the yellow solid (in CDCl3) was identical to that of commercially available dibenzyl diselenide.

InChI:InChI=1/C14H14Se2/c1-3-7-13(8-4-1)11-15-16-12-14-9-5-2-6-10-14/h1-10H,11-12H2

Upstream product

• 100-44-7 benzyl chloride 
• 97732-75-7 (i-PrCp)2TiSe₅ 
• 620-05-3 iodomethylbenzene 
• 98-87-3 benzylidene dichloride 
• 109-73-9 N-butylamine 
• 109-89-7 diethylamine 
• 110-89-4 piperidine 
• 1842-38-2 dibenzyl selenide 
• 67-56-1 methanol 
• 18440-49-8 N-benzyl-N-p-toluenesulfonylhydrazine 
• 6996-92-5 benzeneseleninic acid 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 
• 17107-93-6 Se,Se-dibenzyl triselenocarbonate 

Downstream Products

• 4671-93-6 benzyl selenocyanate 
• 100-51-6 benzyl alcohol 
• 786709-79-3 (3S,4R)-3-[(R)-tert-butyldimethylsilyloxyethyl]-4-[(phenylmethyl)seleno]-2-azetidinone 
• 852063-33-3 ethyl 4-oxo-4-(2-(benzylseleno)pyridin-3-yl)butyrate 
• 342774-77-0 [Pd₂Cl₂(SeCH₂C₆H₅)2(P(CH₃)2C₆H₅)2] 
• 342774-77-0 [Pd₂Cl₂(SeCH₂C₆H₅)2(P(CH₃)2C₆H₅)2] 
• 342774-81-6 [Pt₂Cl₂(SeCH₂C₆H₅)2(P(C₃H₇)3)2] 
• 342774-78-1 [Pd₂Cl₂(SeCH₂C₆H₅)2(P(C₆H₅)3)2] 
• 342774-76-9 [Pd₂Cl₂(SeCH₂C₆H₅)2(P(C₄H₉)3)2] 
• 342774-83-8 [Pt₂(CH₃)2(SeCH₂C₆H₅)2(P(CH₃)2C₆H₅)2] 
• 342774-79-2 [Pd₂(CH₃)2(SeCH₂C₆H₅)2(P(C₆H₅)3)2] 
• 342774-74-7 [Pt(SeCH₂C₆H₅)2(C₂H₄(P(C₆H₅)2)2)] 
• 342774-80-5 [Pt₂Cl₂(SeCH₂C₆H₅)2(P(C₂H₅)3)2] 

Relevant articles and documents

Reactions of selenobenzamide and alkyl halides. Synthesis of dialkyl selenides and diselenides

In the absence of base, the reaction of selenobenzamide with alkyl halides gives the dialkyl diselenides as the major product. While the reaction of selenobenzamide and an alkyl halide is carried out in a 1:2 molar ratio and in the presence of strong base, the dialkyl selenides predominate.

Chemoselective synthesis of fuctionalized diselenides

The action of LiEt3BH or DIBAL-H on various functionalized selenocyanates was proven to be an efficient means to establish chemoselectively the diselenide bond, under very mild conditions. The mechanism was shown to involve a selenophilic hydri

A convenient one-pot synthesis of dibenzyl diselenides under microwave irradiation conditions

A simple, rapid and efficient method for the synthesis of dibenzyl diselenides under microwave irradiation is reported. The effect of microwave irradiation power, times and solvent on the reaction is investigated.

An efficient and practical method for the selective synthesis of sodium diselenide and diorganyl diselenides through selenium reduction

Studies on an efficient and practical method for the selective synthesis of diorganyl diselenides over diorganyl selenides are presented. Considering the discrepancies between reports on organoselenium compounds, we wanted to establish a tolerable synthetic method for diorganyl diselenides and investigate their characteristics. We optimized reaction conditions for sodium diselenide preparation using selenium, NH2NH2·H2O, and NaOH and, by treating the obtained sodium diselenide with various alkyl or aryl halides, achieved the selective synthesis of diorganyl diselenides in modest to good yields (57–88%) with good reproducibility. We further studied the mechanistic implication, the effects of solvent changes, and the stability of diorganyl diselenides.

A synthetic method for diselenides under phase-transfer conditions

Diselenides were easily prepared in high yields by the alkylation of sodium diselenide on halides in water under phase-transfer conditions.

Selenocyanation using a combined reagent of triphenylphosphine and selenocyanogen. A new and simple synthesis of alkyl selenocyanates and symmetrical alkyl diselenides from alcohols

A novel reagent Ph3SeCN)2, easily prepared by adding an equimolar amount of tri-phenylphosphine to selenocyanogen solution in methylene chloride and tetrahydrofuran reacts below -60° with primary alcohols to produce directly the corr

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The Convenient Syntheses of Organoselenium Reagents

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Aqueous phase preparation method of dialkyl diselenide ether compound

The method comprises the following steps: taking the compound represented by the formula (II) as a reaction raw material and I as a reaction raw material, and taking water or ethanol as a solvent under Se 40 - 75 °C conditions to obtain the reaction liquid to obtain the dialkyl diselenium ether compound shown in the formula (II KOH). The reaction is short in reaction time, does not need a metal catalyst, uses water as a solvent, and belongs to green and environment-friendly reaction. Economy, high efficiency, green, environmental protection.

Lead optimization generates selenium-containing miconazole CYP51 inhibitors with improved pharmacological profile for the treatment of fungal infections

A series of selenium-containing miconazole derivatives were identified as potent antifungal drugs in our previous study. Representative compound A03 (MIC = 0.01 μg/mL against C.alb. 5314) proved efficacious in inhibiting the growth of fungal pathogens. However, further study showed lead compound A03 exhibited potential hemolysis, significant cytotoxic effect and unfavorable metabolic stability and was therefore modified to overcome these drawbacks. In this article, the further optimization of selenium-containing miconazole derivatives resulted in the discovery of similarly potent compound B17 (MIC = 0.02 μg/mL against C.alb. 5314), exhibiting a superior pharmacological profile with decreased rate of metabolism, cytotoxic effect and hemolysis. Furthermore, compound B17 showed fungicidal activity against Candida albicans and significant effects on the treatment of resistant Candida albicans infections. Meanwhile, compound B17 not only could reduce the ergosterol biosynthesis pathway by inhibiting CYP51, but also inhibited biofilm formation. More importantly, compound B17 also shows promising in vivo efficacy after intraperitoneal injection and the PK study of compound B17 was evaluated. In addition, molecular docking studies provide a model for the interaction between the compound B17 and the CYP51 protein. Overall, we believe that these selenium-containing miconazole compounds can be further developed for the potential treatment of fungal infections.

Hydrolysis-Based Small-Molecule Hydrogen Selenide (H2Se) Donors for Intracellular H2Se Delivery

Hydrogen selenide (H2Se) is a central metabolite in the biological processing of selenium for incorporation into selenoproteins, which play crucial antioxidant roles in biological systems. Despite being integral to proper physiological function, this reactive selenium species (RSeS) has received limited attention. We recently reported an early example of a H2Se donor (TDN1042) that exhibited slow, sustained release through hydrolysis. Here we expand that technology based on the P-Se motif to develop cyclic-PSe compounds with increased rates of hydrolysis and function through well-defined mechanisms as monitored by 31P and 77Se NMR spectroscopy. In addition, we report a colorimetric method based on the reaction of H2Se with NBD-Cl to generate NBD-SeH (λmax = 551 nm), which can be used to detect free H2Se. Furthermore, we use TOF-SIMS (time of flight secondary ion mass spectroscopy) to demonstrate that these H2Se donors are cell permeable and use this technique for spatial mapping of the intracellular Se content after H2Se delivery. Moreover, these H2Se donors reduce endogenous intracellular reactive oxygen species (ROS) levels. Taken together, this work expands the toolbox of H2Se donor technology and sets the stage for future work focused on the biological activity and beneficial applications of H2Se and related bioinorganic RSeS.