103595-81-9

Usage

Uses

Used in Catalysis:
Phenol, 2,2'-[1,2-ethanediylbis(nitrilomethylidyne)]bis[4,6-bis(1,1-dimethylethyl)is used as a catalyst in certain chemical reactions due to its ability to facilitate the process and enhance the reaction rate. Its unique structure allows it to interact with reactants and intermediates, promoting the desired transformation.
Used in Coordination Chemistry:
In coordination chemistry, Phenol, 2,2'-[1,2-ethanediylbis(nitrilomethylidyne)]bis[4,6-bis(1,1-dimethylethyl)is used as a ligand to form coordination complexes with metal ions. Its multiple donor atoms and flexible structure enable it to chelate with metals, creating stable complexes with potential applications in catalysis, sensing, and materials science.
Used in Pharmaceutical Industry:
Phenol, 2,2'-[1,2-ethanediylbis(nitrilomethylidyne)]bis[4,6-bis(1,1-dimethylethyl)is used as a building block in the synthesis of pharmaceutical compounds. Its structural diversity and reactivity make it a valuable component in the development of new drugs, particularly in the areas of medicinal chemistry and drug design.
Used in Materials Science:
In materials science, Phenol, 2,2'-[1,2-ethanediylbis(nitrilomethylidyne)]bis[4,6-bis(1,1-dimethylethyl)is used as a precursor for the synthesis of advanced materials. Its unique structure can be incorporated into polymers, dendrimers, or other complex molecules, contributing to the development of new materials with tailored properties for various applications.
It is important to handle Phenol, 2,2'-[1,2-ethanediylbis(nitrilomethylidyne)]bis[4,6-bis(1,1-dimethylethyl)with caution due to its potentially hazardous nature. Proper safety measures should be in place when working with this chemical to ensure the safety of researchers and the environment.

Upstream product

• 107-15-3 ethylenediamine 
• 405202-99-5 (2,4-di-tert-butyl-6-({2-[(3,5-di-tert-butyl-2-hydroxy-benzylidene)-amino]-phenylimino}-methyl)-phenol) 
• 37942-07-7 3,5-di-tert-butyl-2-hydroxybenzaldehyde 

Downstream Products

• 882071-01-4 [N,N'-bis(3,5-di-tert-butylsalicylidene)ethylenediamino](diphenyl-tert-butylsiloxy)scandium(III) 
• 849060-35-1 Al(phenolato)(N,N'-bis(3,5-di-tert-butylsalicylidene)-ethylenediamine(-2H)) 
• 63551-08-6 N,N'-bis(2-hydroxy-3,5-di-tert-butylbenzyl)-1,2-ethylenediamine 
• 1027326-63-1 Al(OC₆F₅)(N,N'-bis(3,5-di-tert-butylsalicylidene)-ethylenediamine(-2H)) 
• 1027326-62-0 Al(OC₆H₄-p-OMe)(N,N'-bis(3,5-di-tert-butylsalicylidene)-ethylenediamine(-2H)) 

Relevant academic research and scientific papers

Complexation of High-Valency Mid-Actinides by a Lipophilic Schiff Base Ligand: Synthesis, Structural Characterization, and Progress toward Selective Extraction

Separation of U, Np, and Pu from used nuclear fuel (UNF) would result in lower long-Term radiotoxicity, alleviating constraints on the storage and handling of the material. The complexity of UNF requires several industrial-Scale processes with multiple waste streams. A one-Step solution to the group removal of the elements, U-Pu, is desirable. Here we present a possible solution to group actinide separation utilizing the unique dioxy conformation of An(V/VI) cations and demonstrate the ability of a tetradentate lipophilic Schiff base ligand (L) to yield isostructural complexes of the general formula [(AnVIO2)(L)(CH3CN)] (where An = U, Np, or Pu). Extraction of An(VI) with the ligand follows the order U > Pu > Np, likely reflecting the decreased stability of the hexavalent actinide across the series. While the results indicate a promising path toward a one-Step process, further improvement in the ligand stability and control of the redox chemistry is required.

Hydroxy- and alkoxy-bridged dinuclear uranyl-Schiff base complexes: Hydrolysis, transamination and extraction studies

The reaction of uranyl nitrate with 1,3-bis(salicylideneamino)-2-propanol (H3L1) and 1,3-bis(3,5-di-tert-butylsalicylideneamino)-2-propanol (H3L2) in the presence of triethylamine (Et3N) yielded hydroxy- and alkoxy-bridged dinuclear complexes; [(UO2) 2(L1)(OH)(MeOH)2]?(MeOH)2 (1?(MeOH)2) and [(UO2)2(L2)(OH)(MeOH) 2]?(MeOH)2 (2?(MeOH)2). The crystal structures of 1?(DMF)2 and 2?(DMF)2 exhibit an unsymmetrical central U2O2 core involving bridging alkoxy- and hydroxy-oxygen atoms. The geometry around the uranium center in 1?(DMF)2 and 2?(DMF)2 is that of a distorted pentagonal bipyramid with the solvent molecule occupying the fifth coordination site. The flexible nature of the ligand backbone is more pronounced in 2?(DMF)2 compared to 1?(DMF)2, yielding two molecules per unit cell in different conformations. Under similar reaction conditions, using ethylenediamine as a base, the respective Salen-based uranyl compounds, [UO2(Salen)(MeOH)] (3) and [UO2(Bu t2-Salen)(MeOH)] (4) are obtained due to transamination of the ligand backbone. Complexes 1?(MeOH)2 and 2?(MeOH) 2 when reacted with an excess of ethylenediamine failed to yield the respective Salen-based complexes, 3 and 4, respectively. The new compounds have been characterized using solution (NMR and UV-Vis) and solid-state (IR, X-ray crystallography) techniques. Hydrolysis of 1?(MeOH)2 and 2?(MeOH)2 in the pH range 1-14 was studied using UV-Vis spectroscopy and compared with the hydrolysis of 3 and [UO2(Salophen) (MeOH)] (5). A two-phase extraction study suggests quantitative removal of uranyl ions from the aqueous phase at higher pH conditions. The Royal Society of Chemistry 2008.

Salen-based coordination polymers of manganese and the rare-earth elements: Synthesis and catalytic aerobic epoxidation of olefins

Treatment of N,N'-bis(4carboxysalicylidene)ethylenediamine (H 4L), with MnCl2·(H2O)4, and Ln(NO3)3·(H2O)m (Ln=Nd, Eu, Gd, Dy, Tb), in the presence of N,N-dimethylforma

Direct observation of enantiomer discrimination of epoxides by chiral salen complexes using ENDOR

Electron nuclear double resonance (ENDOR) spectroscopy was used to investigate the weak enantioselective binding between chiral salen complexes [VO(1)] ((R,R)- and (S,S)-vanadyl N,N-bis(3,5-di-tert-butylsalcylidene)-1,2-cyclohexanediamine) and chiral epoxides (e.g., (R)-/(S)-propylene epoxide, 5) in frozen (10 K) solution. Differences in epoxide binding by enatiomers of [VO(1)] was evidenced by changes to the 1H epoxide derived peaks in the ENDOR spectra, such that (R,R)-[VO(1)] + (R)-5 and (R,R)-[VO(1)] + (S)-5 yield noticeably different spectra. These changes were assigned to the small structural differences between the diastereomeric metal-epoxide adducts. Simulation of the spectra revealed differences in the VO...1Hepoxide distances for the diastereomeric pairs, which was confirmed by a complementary set of density functional theory (DFT) calculations. While the epoxide molecule is very weakly coordinated, ENDOR measurements of the racemic complex in racemic epoxide nevertheless indicated the preferential coordination of the (R)-5 to (R,R)-[VO(1)] (likewise (S)-(5) to (S,S)-[VO(1)]), which is favored over the binding of (S)-5 epoxide to (R,R)-[VO(1)] (and likewise (R)-5 epoxide to (S,S)-[VO(1)]). This demonstrates the unique power of the ENDOR technique to resolve weak chiral interactions for which EPR spectroscopy alone lacks sufficient resolution. Copyright

Salen manganese (III) complexes as catalysts for R-(+)-limonene oxidation

The epoxidation of R-(+)-limonene using in situ generated dimethyldioxirane (DMD) as the oxidizing agent and four Jacobsen-type catalysts ((R,R)-Jacobsen, (S,S)-Jacobsen, racemic Jacobsen and achiral Jacobsen) was examined. The effect of the amount of KHSO5 and acetone in the catalyzed and un-catalyzed reaction was also assessed. The main reaction products were diepoxide and endocyclic monoepoxide. In the absence of catalyst, the amount of KHSO5 did not significantly influence conversion and selectivity. The catalyst can be segregated to a different phase and separated from the reaction media when the amount of KHSO5 is above the stoichiometric ratio, R-(+)-limonene/KHSO5 = 0.5 mmol/mmol, and acetone/mmol R-(+)-limonene = 2 mL/mmol. However, when the amount of KHSO5 is below the stoichiometric ratio (R-(+)-limonene/KHSO5 = 1.5 mmol/mmol) the catalyst is difficult to separate. Under the reaction conditions of this study, when the catalyst is segregated, no effect of the catalyst chiral center, (R,R)-Jacobsen or (S,S)-Jacobsen, was found on conversion and selectivity. Additionally, the (R,R)-Jacobsen's catalyst proved to be very stable to oxidative degradation.

Synthesis and Characterization of Structurally Diverse Alkaline-Earth Salen Compounds for Subterranean Fluid Flow Tracking

A family of magnesium and calcium salen-derivatives was synthesized and characterized for use as subterranean fluid flow monitors. For the Mg complexes, di-n-butyl magnesium ([Mg(Bun)2]) was reacted with N,N′-ethylene bis(salicyliden

Oxidative Desulfurization of Dibenzothiophene Using Cobalt (II) Complexes with Substituted Salen-Type Ligands as Catalysts in Model Fuel Oil

Three cobalt(II)-salen complexes (CoL1, CoL2 and CoL3) were synthesized via the reaction of the three tetradentate ligands as N,N′-ethylenebis(salicylimine) L1, N,N′-ethylenebis(3-tert-butylsalicylimine) L2 and N,N′-ethylenebis(3,5-di-tert-butylsalicylimine) L3, with a stoichiometric amount of cobalt(II) acetate tetrahydrate, respectively. All the three complexes were studied as oxidative desulfurization catalyst on dibenzothiophene taken in model fuel oil n-dodecane. The acetonitrile used as an extracting solvent and H2O2 as an oxidant. Comparatively CoL3 proved to be the best catalyst which showed the 76% DBT removal at the optimized conditions. The nth-order kinetic model is the best way to represent oxidation kinetics of complexes. Graphic Abstract: [Figure not available: see fulltext.]This cobalt(II) Schiffs base complexes were studied as catalyst for oxidative desulfurization of dibenzothiphene (DBT) taken as model sulphur compounds in fuel model oil (n-dodecane) using H2O2 as oxidant and acetonitrile as extracting solvent for DBT sulfone in a batch experiment.

Alteration of electronic effect causes change in rate determining step: Oxovanadium(IV)–salen catalyzed sulfoxidation of phenylmercaptoacetic acids by hydrogen peroxide

Sulfoxidation of a series of phenylmercaptoacetic acids (PMAA) by hydrogen peroxide catalysed by oxovanadium(IV)–salen complexes has been carried out spectrophotometrically in 100% acetonitrile medium. The formation and involvement of hydroperoxovanadium(

Site-Selective Copper-Catalyzed Azidation of Benzylic C-H Bonds

Site selectivity represents a key challenge for non-directed C-H functionalization, even when the C-H bond is intrinsically reactive. Here, we report a copper-catalyzed method for benzylic C-H azidation of diverse molecules. Experimental and density functional theory studies suggest the benzyl radical reacts with a CuII-azide species via a radical-polar crossover pathway. Comparison of this method with other C-H azidation methods highlights its unique site selectivity, and conversions of the benzyl azide products into amine, triazole, tetrazole, and pyrrole functional groups highlight the broad utility of this method for target molecule synthesis and medicinal chemistry.

Investigation of the dinuclear effect of aluminum complexes in the ring-opening polymerization of ε-caprolactone

A series of aluminum (Al) complexes bearing hydrazine-bridging Schiff base and salen ligands were synthesized and investigated as catalysts for the ring-opening polymerization of ε-caprolactone (CL). The introduction of steric bulky groups increases the catalytic activity of the corresponding mononuclear aluminum complex. However, the opposite phenomenon was observed in dinuclear Al complexes bearing salen ligands because the steric repulsion reduced the cooperative activation mechanism in the dinuclear Al system. Among these Al complexes, LN2Bu-Al2Me4 bearing a hydrazine-bridging Schiff base ligand had the highest catalytic activity, approximately 3- to 11-fold higher than that of dinuclear Al complexes bearing salen ligands and mononuclear Al complexes bearing Schiff base ligands. Density functional theory calculations revealed that the mechanism of the coordination of CL to one Al center was initiated by the benzyl alkoxide of another Al center.