22077-56-1

Basic information

• Product Name: Benzene, 1,1'-selenobis[2-methyl-
• CAS NO: 22077-56-1
• Molecular Formula: C14H14Se
• Molecular Weight: 261.225
• Mol File: 22077-56-1.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-selenobis[2-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-selenobis[2-methyl-(22077-56-1)
• EPA Substance Registry System: Benzene, 1,1'-selenobis[2-methyl-(22077-56-1)

Safety Data

• Hazardous Substances Data: 22077-56-1(Hazardous Substances Data)

Upstream product

• 616-99-9 bis(2-tolyl) mercury 
• 7727-15-3 aluminium bromide 
• 108-88-3 toluene 
• 56-23-5 tetrachloromethane 
• 109966-02-1 dibromo-di-o-tolyl-λ⁴-selane 
• 615-37-2 ortho-methylphenyl iodide 
• 74-88-4 methyl iodide 
• 95-46-5 2-methylphenyl bromide 
• 16419-60-6 2-Methylphenylboronic acid 
• 10050-08-5 tri-o-tolylbismuth 
• 2028-34-4 o-toluene-diazonium chloride 
• 33872-80-9 o-tolyl magnesium chloride 
• 95-53-4 o-toluidine 
• 2093-46-1 2-methylphenyl diazonium tetrafluoroborate 

Downstream Products

• 605-39-0 2,2'-dimethyl-1,1'-biphenyl 
• 109966-02-1 dibromo-di-o-tolyl-λ⁴-selane 
• 142073-24-3 λ⁴-(di-2-tolyl)dichloroselane 
• 42778-04-1 2-tolyl benzyl selenide 
• 1292289-74-7 [(Pd2(μ-o-tolylselenolate)2)2(μ-acetate)4] 
• 25862-13-9 di-o-tolyl selenoxide 
• 135285-79-9 C₂₁H₂₀NSe⁽¹⁺⁾*F₆P^(1-) 
• 128921-59-5 bis(2-bromomethylphenyl)selenide 

Relevant articles and documents

Synthesis of Diaryl Selenides via Palladium-Catalyzed Debenzylative Cross-Coupling of Aryl Benzyl Selenides with Aryl Bromides

Herein, we report a novel method for synthesizing diaryl selenides from aryl benzyl selenides and aryl bromides via debenzylative cross-coupling with a Pd/NIXANTPHOS-catalyst. NIXANTPHOS outperformed other commonly used bi- and monodentate ligands examined in this novel transformation. This reaction system displays wide functional group tolerance and excellent substrate scope. The transformation broadens the scope of palladium-catalyzed debenzylative processes to use selenolate anions as a leaving group. Its potential for practical synthetic applications was demonstrated with the gram scale synthesis of 4-chlorophenyl phenyl selenide.

Diarylation of chalcogen elements using arylboronic acids via copper- or palladium-catalyzed oxidative coupling

Transition metal-catalyzed diarylations of sulfur, selenium and tellurium were achieved using arylboronic acids in air. A copper-catalyzed reaction of sulfur or selenium efficiently yielded numerous symmetrical diaryl sulfides or selenides in the presence of NH4BF4. However, the diarylation of tellurium was not possible using this method, and required a palladium catalyst in the presence of KI and air for the reaction to proceed.

A novel and efficient synthesis of selenides

Under nitrogen atmosphere, a simple and efficient procedure for the synthesis of symmetrical selenides has been developed by the reaction of aryl or alkyl halides with magnesium (1.5 equiv) and elemental selenium (1.0 equiv) in the absence of catalyst and ligand in THF and toluene under reflux at 86°C. This protocol has been utilized for the synthesis of a variety of symmetrical selenides in good to excellent yields. ARKAT-USA, Inc.