153625-67-3

Basic information

• Product Name: Benzenamine, N,N'-1,2-acenaphthylenediylidenebis[2,6-bis(1-methylethyl)-
• Synonyms: dipp-BIAN;N,N'-bis(2,6-diisopropyl)phenylacenaphthenequinonediimine;N,N'-bis(2,6-diisopropylphenyl)acenaphthenequinonediimine;dpp-bian;1,2-bis(o,o'-bis(isopropyl)phenylimino)acenaphthene;DippBIAN
• CAS NO: 153625-67-3
• Molecular Formula: C36H40N2
• Molecular Weight: 500.727
• Mol File: 153625-67-3.mol
• Article Data: 38

Chemical Properties

• CAS DataBase Reference: Benzenamine, N,N'-1,2-acenaphthylenediylidenebis[2,6-bis(1-methylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, N,N'-1,2-acenaphthylenediylidenebis[2,6-bis(1-methylethyl)-(153625-67-3)
• EPA Substance Registry System: Benzenamine, N,N'-1,2-acenaphthylenediylidenebis[2,6-bis(1-methylethyl)-(153625-67-3)

Safety Data

• Hazardous Substances Data: 153625-67-3(Hazardous Substances Data)

Upstream product

• 62-53-3 aniline 
• 82-86-0 acenaphthene quinone 
• 24544-04-5 2,6-diisopropylbenzenamine 
• 187605-59-0 (2E)-2-[(2,6-diisopropylphenyl)imino]acenaphthylen-1(2H)-one 

Downstream Products

• 155889-91-1 {bis((2,6-diisopropylphenyl)imino)acenaphthene}(maleic anhydride)palladium⁽⁰⁾ 
• 207129-37-1 ((((CH₃)2CH)2C₆H₃N)2(C₂C₁₀H₆))Pd(⁽¹³⁾CH₃)2 
• 184959-74-8 PdBr₂(bis(o,o'-iPr₂C₆H₃-imino)acenaphthene) 
• 733810-42-9 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene germanium 
• 1254829-76-9 [copper(I)(1,2-bis(iPr₂-phenylimino)acenaphthene)(OCHC₆H₄PPh₂)]hexafluorophosphate 
• 1317668-25-9 [{CuI((2,6-iPr₂C₆H₃)2acenaphthenequinonediimine)}2] 
• 1317668-23-7 [{CuCl((2,6-iPr₂C₆H₃)2acenaphthenequinonediimine)}2] 
• 794458-05-2 N,N'-bis(2,6-diisopropylphenyl)acenaphthylene-1,2-diamine 
• 181709-83-1 [Ni(1,2-bis((2,6-diisopropylphenyl)imino)acenaphthene)(COD)] 
• 1239608-47-9 [Ni(1,2-bis((2,6-diisopropylphenyl)imino)acenaphthene)(PhC₂Ph)] 
• 1198767-24-6 C₃₆H₄₀Br₂N₂Se 
• 1192576-31-0 C₃₆H₄₀Cl₂N₂Se 
• 1213265-97-4 tetrachloro(N,N'-bis(2,6-diisopropylphenylimino)acenaphthylene)titanium(IV) 

Relevant articles and documents

Addition of phenylacetylene to a magnesium complex of monoiminoacenaphtheneone (dpp-mian)

In the presence of formic acid, acenaphthenequinone (AQ) reacts with one molar equivalent of 2,6-diisopropylaniline in toluene to give monoiminoacenaphtheneone (3, dpp-mian) in good yield. Reduction of compound 3 with an excess of magnesium in thf results in green crystalline amido-alcoholate [(dpp-mian)Mg(thf)2]2 (4). Crystallization of complex 4 from toluene affords a blue tetramer [(dpp-mian)Mg(thf)]4 (5). Reactions of compounds 4 and 5 with phenylacetylene proceed with C-C bond formation between the alkyne and the dpp-mian ligand to give the monomeric alkynyl-magnesium derivative [(dpp-mian)(PhCCH2)Mg(CCPh)2(thf)]2 (7). Hydrolysis of complex 5 gives metal-free dpp-mian(PhCCH2)H (8). Reaction of 7 with acetylacetone yields [{dpp-mian(PhCCH2)}Mg(acac)]2 (9). Compounds 3-5 and 7-9 have been characterized by IR and NMR spectroscopy; molecular structures of 3, 5, 7, 8 and 9 have been determined by single crystal X-ray analysis.

Aryl-substituted BIAN complexes of iron dibromide: Synthesis, X-ray and electronic structure, and catalytic hydrosilylation activity

Anhydrous iron dibromide complexes bearing bidentate α-diimine ligands ArN=C(Me)-(Me)C=NAr and ArBIAN (BIAN = bis(imino)acenaphthene; Ar = dpp and Mes; dpp = 2,6-diisopropylphenyl; Mes = 2,4,6-trimethylphenyl) have been pr

Aluminum hydrides with radical-anionic and dianionic acenaphthene-1,2-diimine ligands

The reaction of 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene (dpp-bian) with LiAlH4 affords two products regardless of the solvent used (tetrahydrofuran or diethyl ether). These products were isolated as green and colorless crystals. Green

Reactions of [(dpp-Bian)Ln(dme)2] (Ln = Eu, Yb) with some oxidants

Europium and ytterbium complexes [(dpp-Bian)Ln(dme)2] (Ln = Eu (1), Yb(2), dme = 1,2-dimethoxyethane) with redox-active dianionic 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene ligand (dpp-Bian) have been tested in the reactions with nitrous oxide and sulfur. The reactions performed in 1:1 M ratio afford quantitatively neutral dpp-Bian, while the use of a half equivalent of oxidants leads to the europium complex with two radical-anionic dpp-Bian ligands [(dpp-Bian)2Eu(dme)] (3) and the known ytterbium ionic compound [(dpp-Bian)2Yb]?[(dpp-Bian)Yb(dme)2]+ (4). The same products have been produced by the treatment of 1 and 2 with dpp-Bian. The oxidation of 1 and 2 with either sulfur dioxide or sulfur diimide (Me3SiN=)2S proceeds with the total release of the neutral dpp-Bian. DFT calculations performed for 1 and 2 show pure ligand nature of the frontier molecular orbitals in both cases.

Ca(ii), Yb(ii) and Tm(iii) complexes with tri- and tetra-anions of 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene

Reduction of [(dpp-bian)2?M2+(thf)4] (M = Ca, 1; Yb, 6; dpp-bian = 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene) by alkali metals results in heterometallic, [(dpp-bian)3?M2+K+(thf)2]2 (M = Ca, 2; Yb, 7), [(dpp-bian)4?Ca2+A2+(thf)4]2 (A = Na, 3; Li, 4; K, 5), [(dpp-bian)4?Yb2+K2+(thf)4]2 (8) and [(dpp-bian)24?Yb32+K2+(thf)8] (9). The reduction of [(dpp-bian)TmBr(thf)n] (in situ) affords [(dpp-bian)4?Tm3+Na+(thf)]2 (10).

Formation of carbon-carbon bonds between activated alkynes and diimine ligands in the aluminum complexes

The gallium and aluminum complexes containing the redox-active ligand (dpp-bian)Ga-Ga(dpp-bian) (1), (dpp-bian)Al-Al(dpp-bian) (2), or (dpp-bian)AlI(Et2O) (3) (dpp-bian is 1,2-bis[(2,6-diisopropylphenyl) imino]acenaphthene) react with alkyl butynoates Me-C≡C-CO2R (R = Me, Et) to form C-C bonds between the dpp-bian ligand and alkyne. The reaction of complex 1 with methyl 2-butynoate and 4-chloroaniline in a molar ratio of 1: 2: 2 affords 7-(2,6-diisopropylphenyl)-10-methylacenaphtho[1,2-b]pyridin-8(7H)- one (4) containing no gallium. In the reaction of complex 2 with methyl 2-butynoate, alkyne is inserted into the skeleton of the dpp-bian ligand to form 4-(dpp-AIE)-9-(2,6-diisopropylphenyl)-8-(1,3-dpp-2MBIDP)-3,7-dimethoxy-1,5- dialuma-9-aza-2,6-dioxabicyclo[3.3.1]nonadiene-3,7 (5) (dpp-AIE is 1-[2-(2,6-diisopropylphenylimino)acenaphthen-1(2H)-ylidene]ethyl; 1,3-dpp-2MBIDP is 1,3-bis(2,6-diisopropylphenylimino)-2-methyl-2,3-dihydro-1H-phenalen-2-yl). The reactions of complex 3 with methyl and ethyl 2-butynoates afford dimeric derivatives [-OC(OR)=C(2,3-dpp-1MBIDP)Al(I)-]2 (2,3-dpp-1MBIDP is 2,3-bis(2,6-diisopropylphenylimino)-1-methyl-2,3-dihydro-1H-phenalen-2-yl; R = Me (6), Et (7)). The reaction of complex 3 with methyl 2-butynoate gives the product isomeric to compound 6: [-OC(OCH3)=C(1,3-dpp-2MBIDP)Al(I)-] 2 (8), which cleaves THF resulting in complex [-OC(OCH 3)=C(1,3-dpp-2MBIDP)Al(OC4H8I)-]2 (9). Complex (dpp-bian)Al(acac) (10), obtained by the reduction of dpp-bian with aluminum in the presence of Al(acac)3 in diethyl ether at ambient temperature, is inert towards acetylene, phenylacetylene, and alkyl butynoates. Compounds 4-7 and 10 were characterized using IR spectroscopy, and compounds 4, 7, and 10 were additionally characterized by 1H NMR spectroscopy. The structures of compounds 4-7, 9, and 10 were determined by X-ray diffraction analysis.

Simple and Strong Dative Attachment of α-Diimine Nickel (II) Catalysts on Supports for Ethylene Polymerization with Controlled Morphology

Abstract: In this article, preparation of novel spherical MgCl2 supported α-diimine nickel (II) catalysts for ethylene polymerization in slurry phase is reported. α-Diimine ligands were synthesized by condensation reaction of 2, 6-disubstituted alkyls or aryls anilines and Ace naphthoquinone Which have hydroxyl functionality in their para-position. Hydroxyl functionalized α-diimine attached strongly on to the spherical MgCl2 support surface by dative bonding. No linker was needed to attach the complexes onto the support surface and the amount of loaded Nickel was controllable to improve morphology and especially bulk density of polymer powder. A significant reduction in catalysts activity has happened when homogeneous catalysts were supported onto silica but this reduction was decreased when they were supported onto thermally treated spherical MgCl2. As homogeneous bis(N,N′-(4-(3-hydroxyl-propyl)-2,6-di[(4-tert-butyl-phenyl)-phenyl) amino] Ace naphthoquinone Nickel dibromide(d) showed the highest activity among other evaluated homogeneous catalysts, its MgCl2 supported catalyst (d/S-MgCl2) has shown the highest activity among MgCl2 supported catalysts too. These MgCl2 supported catalysts were pre-polymerized in presence of ethylene monomer in the mild polymerization condition to yield a pre-polymerized catalyst with polymer/catalyst weight ratio equal to six. Ethylene polymerization was carried out to make spherical particles of polyethylene without reactor fouling by these pre-polymerized catalysts. Clearly, it is shown in SEM images that the spherical morphology of MgCl2 support is replicated in the produced polymer. The molecular weight and molecular weight distribution of produced polymer with MgCl2 supported catalysts were higher than those produced by homogeneous catalysts. Graphic Abstract: α–Diimine nickel (II) complexes have hydroxy functionality where produce strong dative bonding onto spherical MgCl2. This bonding is strong enough that these catalysts are suitable for slurry polymerization of ethylene without reactor fouling due to catalyst leaching from support. The chemical structure of MgCl2 leads to high active supported catalysts. The molecular weight and polydispersity index of produced polymrers using these supported catalysts are higher than those produced by equivalent homogeneous catalysts and are controllable by selection of appropriate ligand for used α–diimine nickel (II) complex or hydrogen concentration in ethylene polymerization.[Figure not available: see fulltext.].

Robust Buchwald-Hartwig amination enabled by ball-milling

An operationally simple mechanochemical method for the Pd catalysed Buchwald-Hartwig amination of arylhalides with secondary amines has been developed using a Pd PEPPSI catalyst system. The system is demonstrated on 30 substrates and applied in the context of a target synthesis. Furthermore, the performance of the reaction under aerobic conditions has been probed under traditional solution and mechanochemical conditions, the observations are discussed herein.