202277-65-4

Basic information

• Product Name: 2,3-Bis(2,4,6-trimethylphenylimino)butane
• Synonyms: 2,3-Bis(2,4,6-trimethylphenylimino)butane;N,N'-Bis(2,4,6-trimethylphenyl)-1,2-bis(methyl)ethanediimine;N,N'-Bis(2,4,6-trimethylphenyl)butane-2,3-diimine;N,N'-Dimesityl-2,3-butanediimine
• CAS NO: 202277-65-4
• Molecular Formula: C₂₂H₂₈N₂
• Molecular Weight: 320.47112
• Mol File: 202277-65-4.mol

Chemical Properties

• Melting Point: 187.4-188.2℃
• Appearance: /
• CAS DataBase Reference: 2,3-Bis(2,4,6-trimethylphenylimino)butane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Bis(2,4,6-trimethylphenylimino)butane(202277-65-4)
• EPA Substance Registry System: 2,3-Bis(2,4,6-trimethylphenylimino)butane(202277-65-4)

Safety Data

• Hazardous Substances Data: 202277-65-4(Hazardous Substances Data)

Usage

Synonym

Tetradentate Schiff base ligand

Type

Synthetic compound

Class

Schiff bases

Formation

Reaction of 2,3-diaminobutane with 2,4,6-trimethylbenzaldehyde

Applications

Coordination chemistry
Catalysis
Materials science
Organic synthesis
Medicinal chemistry
Antimicrobial properties
Antioxidant properties

Structure

Stable and rigid

Metal ion chelation

Ability to form stable complexes with various transition metal ions

Upstream product

• 431-03-8 dimethylglyoxal 
• 88-05-1 2,4,6-trimethylaniline 

Downstream Products

• 1346170-36-2 C₄₄H₅₆MgN₄ 
• 952594-40-0 [dichloro(1,4-di(o,o',p-trimethylphenyl)-2,3-dimethyl-1,4-diaza-1,3-butadiene)cobalt(II)] 
• 887777-00-6 (2,4,6-Me₃-C₆H₂NC(Me)C(Me)NC₆H₂-2,4,6-Me₃)WCl₂ 
• 881910-75-4 Ph₂Pt((2,4,6-Me₃C₆H₂)-N=C(Me)-C(Me)=N-(2,4,6-Me₃C₆H₂)) 
• 943985-42-0 [CrCl₂(MeCN(2,4,6-(CH₃)3C₆H₂))2] 
• 884842-78-8 [2,4,6-(CH₃)3-C₆H₂NC(CH₃)C(CH₃)NC₆H₂-2,4,6-(CH₃)3]MoCl₂ 
• 917925-89-4 [(2,4,6-Me₃C₆H₂)N=C(Me)-C(Me)=N(2,4,6-Me₃C₆H₂)]2Ni 
• 917925-91-8 [Ni((2,4,6-Me₃C₆H₂)N=C(Me)C(Me)=N(2,4,6-Me₃C₆H₂))(1,5-cyclooctadiene)] 
• 917925-92-9 [(2,4,6-Me₃C₆H₂)N=C(Me)-C(Me)=N(2,4,6-Me₃C₆H₂)]Ni(PhCCPh) 
• 565468-75-9 (CH₃)5C₅IrCl(2,4,6-Me₃C₆H₂)NCMeCMeN(2,4,6-Me₃C₆H₂)Cl 
• 404373-45-1 ((2,4,6-Me₃C₆H₂)N=C(Me)C(Me)=N(2,4,6-Me₃C₆H₂))PtMe₂ 

Relevant articles and documents

Sterically hindered diazabutadienes (DABs): Competing reaction pathways with MeLi

Treatment of N,N′-bis(2,6-diisopropylphenyl)-1,4-diaza-2,3-dimethyl- 1,3-butadiene with MeLi results in carbon-carbon bond formation and selective reduction of one of the imine arms to give the N-lithiated salt of the imine/amine, N,N′-bis(2,6-diisopropyl

Synthesis of pentafluorobenzene-based NHC adducts and their catalytic activity in the microwave-assisted reactions of aldehydes

N-Heterocyclic carbenes (NHCs) have been widely used in organometallic chemistry as ligands, as well as standalone organocatalysts in various reactions, mostly using aromatic aldehydes as substrates. We have previously demonstrated the efficiency of azolium-2-carboxylate zwitterions in the hydroxymethylation of aldehydes, especially aliphatic aldehydes, under microwave irradiation. In the present work, we report a series of pentafluorobenzene-based NHC adducts and their efficiency in the hydroxymethylation and self-condensation of aliphatic and aromatic aldehydes using microwave irradiation. The free carbenes are released under the reaction conditions and 1,3-dimesityl-2-(perfluorophenyl)imidazolidine and 1,3-bis(2,6-dimethylphenyl)-2-(perfluorophenyl)imidazolidine proved to be the most potent precatalysts.

A more sustainable and efficient access to IMes·HCl and IPr·HCl by ball-milling

Herein is described a mechanochemical one-pot two-step procedure giving access to various NHC (N-heterocyclic carbene) precursors. This original approach enabled the production of the widely used IPr·HCl, IMes·HCl, Io-Tol·HCl and ICy·HCl in much better yields than conventional solvent-based procedures, while the environmental impact was drastically reduced.

Mechanochemistry for facilitated access to N,N-diaryl NHC metal complexes

A user-friendly and solvent-free mechanosynthetic strategy allowed light-sensitive silver(i) complexes featuring N,N-diaryl N-heterocyclic carbenes (NHC), including challenging and sterically hindered ligands, to be yielded efficiently. The first transmet

Electrophilic RhI catalysts for arene H/D exchange in acidic media: Evidence for an electrophilic aromatic substitution mechanism

A series of new rhodium (I) complexes supported by bidentate nitrogen-donor ligands with varying electronic and steric properties were synthesized in situ and evaluated for catalytic arene C–H/D activation. In trifluoroacetic acid (HTFA), these complexes are proposed to mediate H/D exchange of arene C–H/D bonds by an electrophilic aromatic substitution mechanism that involves Rh-mediated activation of HTFA (or DTFA). DFT calculations support the proposed pathway for the H/D exchange reactions.

Unraveling the synthesis of homoleptic [Ag(N, N -diaryl-NHC)2]Y (Y = BF4, PF6) complexes by ball-milling

A user-friendly and general mechanochemical method was developed to access rarely described NHC (N-heterocyclic carbene) silver(i) complexes featuring N,N-diarylimidazol(idin)ene ligands and non-coordinating tetrafluoroborate or hexafluorophosphate counter anions. Comparison with syntheses in solution clearly demonstrated the superiority of the ball-milling conditions.

Heteroatom-substituted secondary phosphine oxides for Suzuki-Miyaura cross-coupling reactions

Several di-substituted diimines (3a–3f) and heteroatom-substituted unsaturated secondary phosphine oxides (HASPO, 6a–6f) were prepared and characterized. Compounds 6a–6f are regarded as pre-ligands because of their ability of tautomerization to heteroatom-substituted phosphinous acid (HAPA, 7a–7f). An unexpected 3e-coordinated palladium dibromide 8e was observed from the reaction of compound 6e with PdBr2. Molecular structures of pre-ligands 6a, 6c, and 6e, as well as palladium complexes 8e were determined by single crystal X-ray diffraction methods. When pre-ligand 6a was applied to palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, satisfactory yields were obtained. Density functional theory were employed to examine the electronic properties of HASPO 6a–6f pre-ligands, their corresponding 1,3-di-N-substituted tautomers 7a–7f, and the saturated counterpart 7as of 7a. Compound 7a is the most effective and genuine ligand in Suzuki-Miyaura reaction that is confirmed by its higher-lying lone-pair (LP) molecular orbital (HOMO-1). The LP orbital of 7c–7f is lower-lying HOMO-5. For each 7c–7f, two conformational rotamers with minute energy difference were located. Hirshfeld charge and population analysis of 7c–7f were also calculated in order to comprehend the electronic properties for these two rotamers for each HAPAs. Besides, the steric effect of HAPAs was estimated in terms of the Percent Buried Volume (%Vbur). This model has shown that 7a has similar steric property to that of PCy3, which is an effective ligand in Suzuki-coupling reactions.

Highly active and cis-1,4 selective polymerization of 1,3-butadiene catalyzed by cobalt(II) complexes bearing α-diimine ligands

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An α-Diimine-Nickel(II) catalyst bearing an electron-withdrawing substituent for olefin polymerization

A Br-substituted α-diimine ligand, bis[N,N′-(4-bromo-2,6- dimethylphenyl)imino]-2,3-butadiene L1, and its corresponding Ni(II) complex, {bis[N,N′-(4-bromo-2,6-dimethylphenyl)imino]-2,3-butadiene} dibromonicke [NiBr 2 (L1)], have been synthesize

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(Chemical Equation Presented) A series of 1,3-disubstituted-2-imidazolium carboxylates, an adduct of CO2 and N-heterocyclic carbenes, were synthesized and characterized using single crystal X-ray, thermogravimetric, IR, and NMR analysis. The TG