37826-18-9

Usage

Uses

Used in Organic Synthesis:
Diisopropyl diselenide is used as a reagent in organic synthesis for its strong reductive properties, enabling it to participate in various chemical reactions and facilitate the formation of desired products.
Used in Biochemical Research:
In biochemical research, Diisopropyl diselenide serves as a selenium donor, which is crucial for studying the biological roles and mechanisms of selenium in organisms.
Used in Drug Synthesis:
Diisopropyl diselenide is utilized in the synthesis of certain pharmaceuticals, where its reactivity with metal ions can be harnessed to produce specific drug compounds.
Used in Chemical Industry:
Diisopropyl diselenide is used as a chemical intermediate in the production of various chemical products, taking advantage of its reactivity and properties as an organic selenium compound.

InChI:InChI=1/C6H14Se2/c1-5(2)7-8-6(3)4/h5-6H,1-4H3

Upstream product

• 67-63-0 isopropyl alcohol 
• 67-64-1 acetone 
• 75-26-3 isopropyl bromide 
• 7647-01-0 hydrogenchloride 
• 3777-25-1 isopropyl selenocyanate 
• 75-30-9 2-iodo-propane 
• 75-29-6 isopropyl chloride 
• 2307-69-9 toluene-4-sulfonic acid isopropyl ester 
• 112-29-8 1-bromo dodecane 
• 2973-10-6 diisopropyl sulfate 

Downstream Products

• 35450-17-0 i-propylseleno(phenyl)iodoborane 
• 100033-76-9 (Z)-β-(isopropylselenyl)styrene 
• 187737-37-7 propene 
• 29749-04-0 2-isopropaneselenol 
• 216320-70-6 1,1-di(phenylseleno)-2-(p-toluenesulfonyl)ethene 

Relevant academic research and scientific papers

Convenient route to dialkyl diselenides from alkyl tosylates. Synthesis of di(cis-myrtanyl) diselenide

A one-step method for the synthesis of dialkyl diselenides, by reaction of alkyl tosylates with sodium diselenide is described. Three variants of the synthesis, using as an example the preparation of optically active di(cis-myrtanyl) diselenide, are compared.

Sterically encumbered hexakis(alkylseleno)benzenes: conformational behavior of hexakis(iso-propylselenomethyl)benzene toward Hg2+ ions on selective recognition

An efficient synthesis and structural aspects of a novel class of hexakis(alkylseleno)benzenes [(RSeCH2)6C6] (R = Me, iPr, nBu, sBu, tBu, nPn, nHx, nOct, 1-methylnaphthalene) by the reaction of hexakis(bromomethyl)benzene with RSe- ions is demonstrated. Preliminary data on ion-sensing properties reveal that these species may act as selective ionophores for Hg2+ ions.

Sodium Selenosulfate from Sodium Sulfite and Selenium Powder: An Odorless Selenylating Reagent for Alkyl Halides to Produce Dialkyl Diselenide Catalysts

Na 2 SeSO 3, which can be generated in situ by the reaction of Na 2 SO 3 with Se power, was found to be an odorless reagent for the selenenylation of alkyl halides to produce dialkyl diselenides. These products have been recently shown to be good catalysts for the Baeyer-Villiger oxidation of carbonyl compounds, for the selective oxidation of alkenes, or for the oxidative deoximation of oximes. By using aqueous EtOH as the solvent and avoiding the generation of a malodourous selenol intermediate, the selenylation reaction with Na 2 SeSO 3 is much more environmentally friendly than conventional methods. Owing to the cheap and abundant starting materials and selenium reagents, our novel synthetic method reduces the production costs of dialkyl diselenides as organoselenium catalysts, thereby advancing practical applications of organoselenium-catalysis technologies.

A rapid, efficient and green procedure for transformation of alkyl halides/ tosylates to organochalcogens in water

A one-pot and efficient synthesis of dialkyl dichalcogenides (S, Se) in aqueous media under catalyst-free conditions using benzylic, allylic and primary halides with elemental sulfur and selenium has been developed. Also, this procedure was extended to preparation of trisulfides and triselenides from secondary and tertiary halides in same condition. In all cases, products can be obtained in good to excellent yield in short reactions time.

Method for synthesizing diselenides

The invention relates to the technical field of chemical synthesis of organic selenium, in particular to a method for synthesizing diselenides. The method comprises the steps that selenium powder and sodium sulfide nonahydrate are utilized for reacting to generate selenium disodium tetrasulphide, and then selenium disodium tetrasulphide and halohydrocarbon react to prepare the diselenides. According to the provided by the invention, raw materials are simple and easy to obtain, cost is low, the path is short, reaction conditions are mild, and the reaction is easy to operate.

Condition-driven selective syntheses of dialkyl diselenides involving elemental selenium and sodium borohydride

Dialkyl diselenides have been prepared from alkyl halides, sodium borohydride and elemental selenium using two different methods. One of them involves the intermediate formation of diselenide dianion equivalent ( -SeSe-).

Alkanethioimidoyl Radicals: Evaluation of β-Scission Rates and of Cyclization onto S-Alkenyl Substituents

Thioimidoyl radicals were generated by addition of alkylsulfanyl radicals to alkyl isonitriles and were characterized by electron paramagnetic resonance (EPR) spectroscopy. The β-scissions of their C·S-C bonds were studied by variable-temperature EPR spectroscopy and the fragmentation rate constants and activation energies were calculated. The scission rates depend on the stability of the released alkyl radicals but in any case, at room temperature, the processes were fast. Data collected on similar oxyimidoyls showed that their fragmentations are slightly slower compared to those of analogous thioimidoyls. The scission rates of selenoimidoyls could not be studied by EPR and were evaluated by theoretical calculations. EPR experiments also enabled both β-scission and 5-exo ring closure rate constants of two S-but-3-enyl-substituted imidoyl radicals to be determined, showing that cyclization prevails only at low temperatures. Density functional theory (DFT) theoretical calculations predicted that the fragmentation process preferentially occurs from the s-cis rotamers (X-C bond) of the imidoyl radicals. Thio- and seleno-imidoyls (but not oxyimidoyls) prefer s-trans conformations so that their fragmentations involve prior rotation about the X-C bond.

Synthesis of diselenides and selenides from elemental selenium

Sodium hydride is able to reduce elemental selenium to sodium diselenide (Na2Se2), but not to sodium selenide (Na2Se). Dialkyl diselenides and even dialkyl selenides, including unsymmetrical dialkyl selenides, can be nevertheless synthesized using the proper Se/NaH ratio (1/1 or 1/2).

A modified method to prepare diselenides by the reaction of selenium with sodium borohydride

With a 8:1 molar ratio of selenium to borohydride, sodium diselenide can be prepared conveniently and safely in alkaline aqueous or ethanol solution, which can be used directly to synthesise symmetric diselenides in high yields.

Reaction of organic selenocyanates with hydroxides: The one-pot synthesis of dialkyl diselenides from alkyl bromides

The amount of hydroxide used in the reaction with organic selenocyanate determines the identity of the product (see scheme). Dialkyl and diaryl diselenides are efficiently prepared with 0.5 equivalents of hydroxide, whereas the reaction of aryl selenocyanates with at least one molar equivalent of hydroxide leads to the formation of aryl selenolates, R = Ph, Bu, iPr, PhCH2; M = Li, Na, K.