1842-38-2

Basic information

• Product Name: DIBENZYL SELENIDE
• Synonyms: Benzyl selenide;DIBENZYL SELENIDE;(benzylseleno)methylbenzene;phenylmethylselanylmethylbenzene;[(Benzylselanyl)methyl]benzene;Benzene, 1,1'-[selenobis(methylene)]bis-
• CAS NO: 1842-38-2
• Molecular Formula: C₁₄H₁₄Se
• Molecular Weight: 261.22
• Mol File: 1842-38-2.mol
• Article Data: 52

Chemical Properties

• Boiling Point: 362.3°Cat760mmHg
• Flash Point: 172.9°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 4.06E-05mmHg at 25°C
• CAS DataBase Reference: DIBENZYL SELENIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIBENZYL SELENIDE(1842-38-2)
• EPA Substance Registry System: DIBENZYL SELENIDE(1842-38-2)

Safety Data

• Hazardous Substances Data: 1842-38-2(Hazardous Substances Data)

Usage

General Description

Dibenzyl selenide is a chemical compound with the formula (C6H5CH2)2Se. It is a colorless to pale yellow liquid that is insoluble in water but soluble in organic solvents. Dibenzyl selenide is widely used as a reagent in organic synthesis and as a precursor to organoselenium compounds. It is also known for its potential antioxidant and chemopreventive properties, making it an active area of research in the field of medicinal chemistry. Additionally, dibenzyl selenide has been studied for its potential use as a flame retardant and as a compound with promising antiviral activity. However, it is important to note that selenides can be toxic, and caution should be exercised when handling and using this compound.

InChI:InChI=1/C14H14Se/c1-3-7-13(8-4-1)11-15-12-14-9-5-2-6-10-14/h1-10H,11-12H2

Upstream product

• 3204-68-0 benzyldimethylphenylammonium chloride 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 64-17-5 ethanol 
• 1482-82-2 dibenzyl diselenide 
• 908093-98-1 diazodiphenylmethane 
• 75-30-9 2-iodo-propane 
• 4671-93-6 benzyl selenocyanate 
• 4980-70-5 1,3-diphenyl-1-propyne 
• 16645-12-8 benzyl selenol 
• 620-05-3 iodomethylbenzene 
• 100-46-9 benzylamine 
• 66310-10-9 N-benzyl-2,4,6-triphenylpyridinium tetrafluoroborate 
• 630-10-4 selenourea 

Downstream Products

• 55986-20-4 N-(p-tolylsulfonyl)dibenzylselenimide 
• 80447-77-4 dibenzylmethylselenonium tetrafluoroborate 
• 16645-12-8 benzyl selenol 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 77905-74-9 Dibenzyl selenoxide nitric acid adduct 
• 67264-83-9 Dibenzyl-(t-butoxy)selenchlorid 
• 1599461-86-5 3-(benzylselenyl)-1H-indole 
• 849706-60-1 dibenzyl-selenonium-methylide-tribromo-indate(III) 
• 70897-64-2 mer-Rh(Se(C₆H₅CH₂)2)3Cl₃ 
• 350-50-5 benzyl fluoride 
• 538-86-3 benzyl methyl ether 
• 1482-82-2 dibenzyl diselenide 
• 52109-40-7 8-Benzylselenoadenosin-3',5'-phosphorsaeure 

Relevant articles and documents

Reaction of 1,3-bis(alkylseleno)allenes with diphenyl diazomethane

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Bulky Selenium Ligand Stabilized Trans-Palladium Dichloride Complexes as Catalyst for Silver-Free Decarboxylative Coupling of Coumarin-3-Carboxylic Acids

This report describes the syntheses of three new trans-palladium dichloride complexes of bulky selenium ligands. These complexes possess a Cl?Pd?Cl rotor spoke attached to a Se?Pd?Se axle. The new ligands and palladium complexes (C1?C3) were characterized with the help of NMR, HRMS, UV-Vis., IR, and elemental analysis. The single-crystal structure of metal complex C2 confirmed a square planar geometry of complex with trans-orientation. The X-ray structure revealed intramolecular secondary interactions (SeCH—Cl) between chlorine of PdCl2 and CH2 proton of selenium ligand. Variable-temperature NMR data shows coalescence of diastereotopic protons, which indicates pyramidal inversion of selenium atom at elevated temperature. The relaxed potential energy scan of C2 suggests a rotational barrier of ～12.5 kcal/mol for rotation of chlorine atom through Cl?Pd?Cl rotor. The complex C3 possesses dual intramolecular secondary interactions (OCH2—Cl and SeCH2—Cl) with stator ligand. Molecular rotor C2 was found to be a most efficient catalyst for the decarboxylative Heck-coupling under mild reaction conditions. The protocol is applicable to a broad range of substrates with large functional group tolerance and low catalyst loading (2.5 mol %). The mechanism of decarboxylative Heck-coupling reaction was investigated through experimental and computational studies. Importantly the reaction works under silver-free conditions which reduces the cost of overall protocol. Further, the catalyst also worked for decarboxylative arylation and decarboxylative Suzuki-Miyaura coupling reactions with good yields of the coupled products.

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.

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.