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Usage

Uses

Used in Organic Synthesis:
Dibenzyl diselenide is used as a source of the PhSe unit in organic synthesis. This application is valuable for the creation of a wide range of complex organic molecules that can be utilized in different fields, such as pharmaceuticals, materials science, and chemical research.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Dibenzyl diselenide is used to introduce PhSe groups by reacting with a variety of nucleophilic reagents. This process allows for the development of new drugs and therapeutic compounds with potential applications in treating various diseases and medical conditions.
Used in Chemical Research:
Dibenzyl diselenide is also utilized in chemical research for studying the reactivity and properties of the PhSe group. This knowledge can be applied to design and synthesize novel molecules with specific characteristics, which can be beneficial for various scientific and industrial applications.
Used in Material Science:
In the field of material science, Dibenzyl diselenide can be employed to introduce PhSe groups into polymers and other materials. This modification can enhance the properties of these materials, such as their stability, conductivity, or reactivity, making them suitable for specific applications in various industries.
Overall, Dibenzyl diselenide is a versatile compound with a wide range of applications in different industries, including organic synthesis, pharmaceuticals, chemical research, and material science. Its ability to introduce PhSe groups and its unique chemical properties make it a valuable asset in the development of new drugs, materials, and other products.

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

• 16645-12-8 benzyl selenol 
• 6921-34-2 benzylmagnesium chloride 
• 67-56-1 methanol 
• 1842-38-2 dibenzyl selenide 
• 98196-77-1 N-succinylcysteamine 
• 20190-79-8 potassium Se-benzyl selenosulfate 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 110-89-4 piperidine 
• 98-87-3 benzylidene dichloride 
• 100-52-7 benzaldehyde 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 60-29-7 diethyl ether 
• 7732-18-5 water 

Downstream Products

• 463944-47-0 benzyl ethyl selenide 
• 7362-34-7 trimethylselenonium iodide 
• 97030-74-5 Toluol-α-selenigsaeure-anhydrid 
• 81114-23-0 5-benzylselenopentan-2-one 
• 148173-02-8 5-Benzylseleno-2-methylpentanoic acid 
• 7370-56-1 5-(benzylseleno)pentanoic acid 
• 43169-91-1 6-(benzylseleno)hexanoic acid 
• 43169-92-2 7-(benzylseleno)heptanoic acid 
• 148173-03-9 5-Benzylseleno-2-ethylpentanoic acid 
• 121307-67-3 (4-Benzylselanyl-phenyl)-phenyl-methanone 
• 101349-66-0 benzyl(2-phenylethynyl)selane 
• 101316-22-7 C₂₂H₂₀Se₂ 
• 620-83-7 1-methyl-4-(phenylmethyl)benzene 
• 713-36-0 2-benzyltoluene 

Relevant academic research and scientific papers

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.

A77Se NMR study of elemental selenium reduction using NaBH4

Alkylation or arylation of selenide or diselenide anions is a well-established method to obtain organoselenium compounds. Nevertheless, detecting inorganic selenium anions using77Se NMR is still a challenge. In a previous work, alkylation of Na2Se was found sometimes to yield a mixture of organyl selenides/diselenides in variable amounts. In the literature, this mixture is sometimes attributed to the oxidation of an intermediate alkyl selenol during the extraction. To understand this process, a series of experiments using77Se NMR were performed. It was clear from the77Se NMR experiments that NaHSe-and Se22- formation was very dependent on the NaBH4stoichiometry used. After alkylation, alkyl selenol and dialkyl diselenide were identified, proving they were not formed during the extraction step. As a result, alkyl selenols, dialkyl selenides or dialkyl diselenides with a high purity degree were obtained. To achieve high purity and selectivity of the organoselenium compound, the stoichiometric ratio between Se0/NaBH4has to be carefully measured.

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.

Improved method for the synthesis of organic diselenides from organic halides under atmospheric pressure

An improved approach to the synthesis of organic diselenides is reported. The process involves the reaction of organic halides with selenium, carbon monoxide, and water under atmospheric pressure in the presence of an inorganic base, sodium hydroxide, to afford organic diselenides in good yields. Copyright Taylor & Francis Group, LLC.

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.

First example of selenium transfer reaction of primary selenoamides and selenourea. Novel synthesis of dialkyl diselenides from alkyl halides

As selenium transfer reagents, arylselenoamides react with a variety of alkyl halides in ethanol under mild conditions to give dialkyl diselenides in excellent yields.Similarly, alkyl halides treated with selenourea form dialkyl diselenides.The possible mechanism is discussed. Keywords: Selenium; Selenoamides; Diselenides; Selenourea; Alkyl halide

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

Structure of "bis(methoxymagnesium)diselenide": A reagent for the introduction of selenium into organic molecules

The reaction of magnesium and selenium in dry methanol has been reported to yield a reagent tentatively identified as bis(methoxymagnesium) diselenide. The dark red-brown solution obtained from this reaction yielded red crystals that crystallized in the monoclinic space group C2/c, a=17.391(4) A, b=15.823(3) A, c=21.626(4) A, β=110.71(3)°, V=5566.5(19) A3, Z=4, R=0.0350, wR2=0.0850 for 4930 reflections. X-ray crystallographic analysis of this reagent showed it to be dodecamethanol-tetramethoxy-di(μ4-hydroxy)tetra(μ3- methoxy)hexamagnesium hexaselenide, Mg6(μ4-OH) 2(μ3-OCH3)4(OCH3) 4(CH3OH)12]Se6·2CH 3OH (1), not the bis(methoxymagnesium) diselenide as previously described. The structure of 1 is composed of six magnesium ions and six bridging oxygen-containing ligands in a face-sharing cubic arrangement.