74663-75-5

Basic information

• Product Name: Glyoxal bis(2,6-diisopropylanil), N,Nμ-Bis(2,6-diisopropylphenyl)-1,4-diazabutadiene, N,Nμ-Bis(2,6-diisopropylphenyl)ethanediimine
• Synonyms: N,N'-1,2-Ethanediylidenebis[2,6-bis(1-methylethyl)phenylamine];N,N'-Bis(2,6-diisopropylphenyl)-1,4-diazabutadiene;N,N'-Bis(2,6-diisopropylphenyl)ethanediimine;N,N'-Bis(2,6-diisopropylphenyl)glyoxaldiimine;N,N'-bis[2,6-di(propan-2-yl)phenyl]ethane-1,2-diimine;(1E,2E)-1,2-Bis(2,6-Diisopropylphenylimino)ethane;Glyoxal bis(2,6-diisopropylanil), N,Nμ-Bis(2,6-diisopropylphenyl)-1,4-diazabutadiene, N,Nμ-Bis(2,6-diisopropylphenyl)ethanediimine;1,4-Bis(2,6-diisopropylphenyl)-1,4-diaza-1,3-butadiene
• CAS NO: 74663-75-5
• Molecular Formula: C₂₆H₃₆N₂
• Molecular Weight: 376.58
• Mol File: 74663-75-5.mol

Chemical Properties

• Melting Point: 105-109 °C
• Boiling Point: 492.0±55.0 °C(Predicted)
• Appearance: /
• Density: 0.95
• PKA: 1.85±0.50(Predicted)
• CAS DataBase Reference: Glyoxal bis(2,6-diisopropylanil), N,Nμ-Bis(2,6-diisopropylphenyl)-1,4-diazabutadiene, N,Nμ-Bis(2,6-diisopropylphenyl)ethanediimine(CAS DataBase Reference)
• NIST Chemistry Reference: Glyoxal bis(2,6-diisopropylanil), N,Nμ-Bis(2,6-diisopropylphenyl)-1,4-diazabutadiene, N,Nμ-Bis(2,6-diisopropylphenyl)ethanediimine(74663-75-5)
• EPA Substance Registry System: Glyoxal bis(2,6-diisopropylanil), N,Nμ-Bis(2,6-diisopropylphenyl)-1,4-diazabutadiene, N,Nμ-Bis(2,6-diisopropylphenyl)ethanediimine(74663-75-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 74663-75-5(Hazardous Substances Data)

Usage

Uses

Used in Catalyst Preparation:
Glyoxal bis(2,6-diisopropylanil), N,Nμ-Bis(2,6-diisopropylphenyl)-1,4-diazabutadiene, N,Nμ-Bis(2,6-diisopropylphenyl)ethanediimine is used as a reactant in the preparation of derived ruthenium olefin metathesis catalysts. It serves as an N-cyclic carbene ligand, which is crucial for the formation and activity of the catalyst.
Used in Palladium-Catalyzed Aerobic Alcohol Oxidation:
In the chemical industry, this compound is used as a catalyst in palladium-catalyzed aerobic alcohol oxidation reactions. The presence of the a-diimine ligand in the compound supports the catalytic process, leading to efficient and selective oxidation of alcohols.
Used in Regioselective Alkylation:
Glyoxal bis(2,6-diisopropylanil), N,Nμ-Bis(2,6-diisopropylphenyl)-1,4-diazabutadiene, N,Nμ-Bis(2,6-diisopropylphenyl)ethanediimine is also utilized in regioselective alkylation reactions in the presence of ruthenium-bisimine catalytic precursors. Glyoxal bis(2,6-diisopropylanil), N,Nμ-Bis(2,6-diisopropylphenyl)-1,4-diazabutadiene, N,Nμ-Bis(2,6-diisopropylphenyl)ethanediimine's unique structure allows for precise control over the reaction's outcome, resulting in the formation of specific products.
Used in N-Arylation of Aromatic Amines:
Glyoxal bis(2,6-diisopropylanil), N,Nμ-Bis(2,6-diisopropylphenyl)-1,4-diazabutadiene, N,Nμ-Bis(2,6-diisopropylphenyl)ethanediimine is employed in the N-arylation of aromatic amines, a reaction that is essential for the synthesis of various organic compounds and pharmaceuticals. Its role in this process contributes to the formation of the desired aryl-amine products with high selectivity.
Used in Preparation of Ruthenium Nitrosyl Alpha-Diimine and Iminoketone Complexes:
Glyoxal bis(2,6-diisopropylanil), N,Nμ-Bis(2,6-diisopropylphenyl)-1,4-diazabutadiene, N,Nμ-Bis(2,6-diisopropylphenyl)ethanediimine is used in the preparation of ruthenium nitrosyl alpha-diimine and iminoketone complexes. These complexes serve as catalysts for transfer hydrogenation of ketones and atom transfer radical polymerization reactions, which are important processes in the synthesis of various chemicals and materials.

Upstream product

• 131543-46-9 Glyoxal 
• 24544-04-5 2,6-diisopropylbenzenamine 
• 88-05-1 2,4,6-trimethylaniline 
• 4405-13-4 glyoxal trimer dihydrate 
• 768-94-5 1-Adamantanamine 

Downstream Products

• 884639-92-3 2-chloro-1,3-bis(diisopropylphenyl)-1,3-dihydro-1,3,2-diazaphosphol 
• 343930-48-3 [(η(6)-C6Me6)OsCl(1,4-bis(2,6-isopropylphenyl)-1,4-diaza-1,3-butadiene)]PF6 
• 343930-52-9 [(η(5)-C5Me5)RhCl(1,4-bis(2,6-isopropylphenyl)-1,4-diaza-1,3-butadiene)]PF6 
• 343930-54-1 [(η(5)-C5Me5)IrCl(1,4-bis(2,6-isopropylphenyl)-1,4-diaza-1,3-butadiene)]PF6 
• 250285-32-6 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride 
• 915703-81-0 N,N'-bis(2,6-diisopropylphenyl)-2-bromo-2,3-dihydro-1H-1,3,2-diazaborole 
• 198057-39-5 1,3-bis(2,6-diisopropylphenyl)-1,3-diaza-2,2-dichloro-2-silacyclopent-4-ene 
• 101178-21-6 (η5-cyclopentadienyl)Co(III)(η2-N,N'-di(2,6-diisopropylphenyl)diazabutene(2-)) 
• 1585210-14-5 fac-ReBr(CO)₃(N,N′-bis(2,6-diisopropylphenyl)-1,4-diaza-1,3-butadiene) 
• 1585210-09-8 fac-Mn(Br)(CO)₃(N,N′-bis(2,6-diisopropylphenyl)-1,4-diaza-1,3-butadiene) 

Relevant articles and documents

Palladium/Copper-Cocatalyzed Arylsilylation of Internal Alkynes with Acyl Fluorides and Silylboranes: Synthesis of Tetrasubstituted Alkenylsilanes by Three-Component Coupling Reaction

In this Letter, the palladium/copper-cocatalyzed arylsilylation of internal alkynes with acyl fluorides and silylboranes is described. This is the first example in which acyl fluorides have been utilized for the three-component coupling reaction via decarbonylation, yielding a variety of tetrasubstituted alkenylsilanes in moderate to good yields.

Steric effect of NHC ligands in Pd(II)–NHC-catalyzed non-directed C–H acetoxylation of simple arenes

Although there has been a lot of progress in oxidative arene C–H functionalization reactions catalyzed by Pd(II/IV) system, the non-directed, site-selective functionalization of arene molecules is still challenging. It has been established that ligands play a pivotal role in controlling rate- as well as selectivity-determining step in a catalytic cycle involving well-defined metal-ligand bonding. N-heterocyclic carbene (NHC) ligands have had a tremendous contribution in the recent extraordinary success of achieving high reactivity and excellent selectivity in many catalytic processes including cross-coupling and olefin-metathesis reactions. However, the immense potential of these NHC ligands in improving site-selectivity of non-directed catalytic C–H functionalization reactions of simple arenes is yet to be realized, where overriding the electronic bias on deciding selectivity is a burdensome task. The presented work demonstrated an initiative step in this regard. Herein, a series of well-defined discrete [Pd(NHCR′R)(py)I2] complexes with systematically varied degree of spatial congestion at the Pd centre, exerted through the R and R’ substituents on the NHC ligand, were explored in controlling the activity as well as the site-selectivity of non-directed acetoxylation of representative monosubstituted and disubstituted simple arenes (such as toluene, iodobenzene and bromobenzene, naphthalene and 1,2-dichlorobenzene). The resulting best yields were found to be 75% for toluene and 65% for bromobenzene with [Pd(NHCMePh)(py)I2], 75% for iodobenzene and 79% for naphthalene with [Pd(NHCMeMe)(py)I2], and 41% for 1,2-dichlorobenzene with [Pd(NHCCyCy)(py)I2]. Most importantly, with increasing the bulkiness of the NHC ligand in the complexes, the selectivity of the distal C-acetoxylated products in comparison to the proximal ones, was enhanced to a great extent in all cases. Considering the vast library of NHC ligands, this study underscores the future opportunity to develop more strategies to improve the activity and the crucial site-selectivity of C–H functionalization reactions in simple as well as complex organic molecules.

Reactions of a diborylstannylene with CO2and N2O: diboration of carbon dioxide by a main group bis(boryl) complex

The reactions of the boryl-substituted stannylene Sn{B(NDippCH)2}2(1) with carbon dioxide have been investigated and shown to proceedviapathways involving insertion into the Sn-B bond(s). In the first instance this leads to formation of the (boryl)tin(ii) borylcarboxylate complex Sn{B(NDippCH)2}{O2CB(NDippCH)2} (2), which has been structurally characterized and shown to feature a κ2mode of coordination of the [(HCDippN)2BCO2]?ligand at the metal centre.2undergoes B-O reductive elimination in hexane solution (in the absence of further CO2) to give the boryl(borylcarboxylate)ester {(HCDippN)2B}O2C{B(NDippCH)2} (3)i.e.the product of formal diboration of carbon dioxide. Alternatively,2can assimilate a second equivalent of CO2to give the homoleptic bis(borylcarboxylate) Sn{O2CB(NDippCH)2}2(4), which can be preparedviaan alternative route from SnBr2and the potassium salt of [(HCDippN)2BCO2]?, and structurally characterized as its DMAP (N,N-dimethylaminopyridine) adduct. Structural and reactivity studies also point to the possibility for extrusion of CO from the [(HCDippN)2BCO2]?fragment to generate the boryloxy system [(HCDippN)2BO]?, a ligand which can be generated directly from1viareaction with N2O. The initially formed unsymmetrical species Sn{B(NDippCH)2}{OB(NDippCH)2} has been shown to be amenable to crystallographic study in the solid state, but to undergo ligand redistribution in solution to generate a mixture of1and the bis(boryloxy) complex Sn{OB(NDippCH)2}2

Iron-based compound as well as preparation method and application thereof

The invention discloses an iron-based compound as well a a preparation method and application thereof, and belongs to the technical field of thickened oil viscosity reduction exploitation. The preparation method comprises the following steps of: mixing 1, 3-bis (2, 6-diisopropyl-1-phenyl) imidazolium chloride, potassium tert-butoxide and a first organic solvent, and carrying out stirring for a reaction to obtain free N-heterocyclic carbene; and mixing the free N-heterocyclic carbene, an iron source and a second organic solvent, and carrying out stirring for a reaction to obtain the iron-based compound. The invention also comprises an iron-based compound prepared by the preparation method. In addition, the invention also provides application of the iron-based compound in catalytic degradation of thickened oil. The degradation rate of the iron-based compound provided by the invention on heavy oil can reach 85%.

Preparation method of NHC-PdCl2-3-chloropyridine complex

The invention relates to a preparation method of an NHC-PdCl2-3-chloropyridine complex. The preparation method comprises the following steps: subjecting 2,6-diisopropylaniline, glyoxal and acetic acid to reacting in an ethanol solvent for 2-4 days to obtain glyoxal-bis-(2,6-diisopropylphenyl)imine; stirring a mixed solution of glyoxal-bis-(2,6-diisopropylphenyl)imine, chloromethylethyl ether, tetrahydrofuran and water at 30-50 DEG C for a reaction for 10-20 hours to obtain 1,3-bis-(2,6-diisopropylphenyl)imidazolium chloride, wherein a molar ratio of glyoxal-bis-(2,6-diisopropylphenyl)imine to water is 1: (2-10); and subjecting 1,3-bis-(2,6-diisopropylphenyl)imidazolium chloride, palladium chloride, cesium carbonate and 3-chloropyridine to reacting for 10-20 hours at a temperature of 60-100 DEG C to obtain [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium (II) dichloride. The method has the advantages that raw materials are easy to obtain, operation is simple, reaction conditions are mild and easy to control and industrial mass production is easy.

Dilithium Amides as a Modular Bis-Anionic Ligand Platform for Iron-Catalyzed Cross-Coupling

Dilithium amides have been developed as a bespoke and general ligand for iron-catalyzed Kumada-Tamao-Corriu cross-coupling reactions, their design taking inspiration from previous mechanistic and structural studies. They allow for the cross-coupling of alkyl Grignard reagents with sp2-hybridized electrophiles as well as aryl Grignard reagents with sp3-hybridized electrophiles. This represents a rare example of a single iron-catalyzed system effective across diverse coupling reactions without significant modification of the catalytic protocol, as well as remaining operationally simple.

N-Heterocyclic carbene palladium (II)-pyridine (NHC-Pd (II)-Py) complex catalyzed heck reactions

A mild, efficient, and practical catalytic system for the synthesis of highly privileged stilbene pharmacophores is reported. This system uses N-heterocyclic carbene palladium (II) Pyridine (NHC-Pd (II)-Py) complex to catalyze the formation of carbon-carbon bonds between olefin derivatives and various bromide. This simple, gentle and user-friendly method can offer a variety of stilbene products in excellent yields under solvent-free condition. And its scale-up reaction has excellent yield and this system can be applied to industrial fields. The utility of this method is highlighted by its universality and modular synthesis of a series of bioactive molecules or important medical intermediates.

Method for preparing substituted aryl ketone by ketone arylation (by machine translation)

The invention provides a method, for preparing substituted aryl ketone, by using a nitrogen heterocyclic carbene catalyst, with a saturated nitrogen heterocyclic carbene structure in an oxygen-containing atmosphere at, through α - catalysis of a nitrogen heterocyclic carbene structure, in a nitrogen heterocyclic carbene catalyst with a saturated nitrogen heterocyclic carbene structure under an alkaline condition, in an oxygen-containing atmosphere and can efficiently prepare various substituted, aryl ketones α - under the condition of containing an oxygen. atmosphere. (by machine translation)

Synthesis method of gamma-aryl substituted ketone compound

The invention relates to a synthetic method of an organic compound, in particular to a method for synthesizing a gamma-aryl substituted ketone compound by using a tertiary cyclobutanol derivative andaryl halide as reaction substrates under the catalytic action of nickel. According to the method, a substituted cyclobutanol compound shown as a formula I and a brominated compound shown as a formulaII are used as raw materials to obtain the gamma-aryl substituted ketone compound shown as a formula III. The nickel acetate tetrahydrate is rich in reserves and low in price, the reaction cost is reduced, and the method can be used for selectively synthesizing the remote gamma-aryl substituted ketone compound.

Incorporation of coinage metal-NHC complexes into heptaphosphide clusters

Cu(i) and Au(i) ions, capped with an N-heterocyclic carbene (NHC), react with (TMS)3P7 (TMS = trimethyl-silyl) to afford an η4-coordinated anion [NHCDippCu-P7(TMS)]- and a neutral trinuclear complex (NHCDippAu)3P7. Protecting the P7 cage with the TMS groups is instrumental in controlling the course of these reactions. This journal is