16486-74-1

Usage

InChI:InChI=1/C8H19N/c1-5-6-7-9-8(2,3)4/h9H,5-7H2,1-4H3

Upstream product

• 71475-20-2 N-n-Butyl-N-t-butylformamid 
• 123-72-8 butyraldehyde 
• 75-64-9 tert-butylamine 
• 71-36-3 butan-1-ol 
• 6852-59-1 tert-butyl-butyliden-amine 
• 6943-47-1 1-tert-butyl-4-methyl-1-aza-1,3-butadiene 
• 109-69-3 n-Butyl chloride 
• 109-65-9 1-bromo-butane 

Downstream Products

• 67651-72-3 N-Butyl-N-tert-butyl-3,4-dichloro-benzamide 
• 67616-62-0 N-Butyl-N-tert-butyl-3-chloro-benzamide 
• 31820-20-9 n-Butyl-tert.-butyl-nitrosamin 

Relevant academic research and scientific papers

Alkaline Earth Metal Aluminates as Catalysts for Imine Hydrogenation

Alkaline earth (Ae) metal complexes with the alanate anion AlH4-have been prepared by salt metathesis between NaAlH4and AeCl2in THF and could be isolated as Mg(AlH4)2·(THF)4, Ca(AlH4)2·(THF)4, and Sr(AlH4)2·(THF)5. The previously reported crystal structure of the Mg alanate complex shows bonding of AlH4-with one bridging hydride, H3Al-(μ-H)-Mg, while the Ca and Sr alanates show a combination of H3Al-(μ-H)-Ae and H2Al-(μ-H)2-Ae bridging. The heteroleptic β-diketiminate complexes (DIPPBDI)Mg(AlH4)·THF and (DIPPBDI)Ca(AlH4)·(THF)2have been prepared by reaction of the corresponding Ae hydride complexes with AlH3·(THF)2[DIPPBDI = DIPP-NC(Me)C(H)C(Me)N-DIPP, where DIPP = 2,6-diisopropylphenyl]. Crystal structures show H2Al-(μ-H)2-Ae bridging. The Ca complex decomposes at room temperature by reduction of the β-diketiminate anion. Density functional theory calculations (B3PW91/def2tzvpp) show that the formation of Ae(AlH4)2from AeH2and AlH3is exothermic by δH (kilocalories per mole): Be, -68.8; Mg, -66.1; Ca, -95.4; Sr, -100.9; Ba, -112.3. Calculations of NPA charges on LiAlH4and the Ae alanate complexes (Ae = Mg, Ca, or Sr) show that these are highly ionic salts in which the charge on AlH4-of approximately -0.95 is hardly dependent on the countercation. Compared to LiAlH4, the Ae alanates are very efficient catalysts for imine hydrogenation, clearly extending the substrate scope. In addition to aldimines RC(H)=NR′ (R/R′ = Ph/tBu, tBu/tBu, nPr/tBu, or Ph/Ph), ketimine PhC(Me)=NtBu could be reduced. The salt [Bu4N+][AlH4-] is catalytically not active, which shows that the s-block metal is crucial. The highest activities were found for the heterobimetallic Ca and Sr alanates.

Cationic Aluminium Complexes as Catalysts for Imine Hydrogenation

Strongly Lewis acidic cationic aluminium complexes, stabilized by β–diketiminate (BDI) ligands and free of Lewis bases, have been prepared as their B(C6F5)4? salts and were investigated for catalytic activity in imine hydrogenation. The backbone (R1) and N (R2) substituents on the R1,R2BDI ligand (R1,R2BDI=HC[C(R1)N(R2)]2) influence sterics and Lewis acidity. Ligand bulk increases along the row Me,DIPPBDIMe,DIPePBDI≈tBu,DIPPBDItBu,DIPePBDI; DIPP=2,6-C(H)Me2-phenyl, DIPeP=2,6-C(H)Et2-phenyl. The Gutmann-Beckett test showed acceptor numbers of: (tBu,DIPPBDI)AlMe+ 85.6, (tBu,DIPePBDI)AlMe+ 85.9, (Me,DIPPBDI)AlMe+ 89.7, (Me,DIPePBDI)AlMe+ 90.8, (Me,DIPPBDI)AlH+ 95.3. Steric and electronic factors need to be balanced for catalytic activity in imine hydrogenation. Open, highly Lewis acidic, cations strongly coordinate imine rendering it inactive as a Frustrated Lewis Pair (FLP). The bulkiest cations do not coordinate imine but its combination is also not an active catalyst. The cation (tBu,DIPPBDI)AlMe+ shows the best catalytic activity for various imines and is also an active catalyst for the Tishchenko reaction of benzaldehyde to benzylbenzoate. DFT calculations on the mechanism of imine hydrogenation catalysed by cationic Al complexes reveal two interconnected catalytic cycles operating in concert. Hydrogen is activated either by FLP reactivity of an Al???imine couple or, after formation of significant quantities of amine, by reaction with an Al???amine couple. The latter autocatalytic Al???amine cycle is energetically favoured.

Stabilization of the hindered urea bond through de-tert-butylation

We report the discovery of an acid-assisted de-tert-butylation reaction that can instantly “turn off” the dynamicity of hindered urea bonds (HUBs) and thus broaden their applications. The reaction is demonstrated to be widely applicable to different hindered urea substrates, leading to improved chemical stabilities and mechanical properties of HUB-containing materials.

In a vapor phase production of asymmetrical sec. tert metylamine

The present application relates to a method for producing unsymmetrical secondary tert-butyl amines by continuous amination in the gas phase, wherein tert-butyl amine is reacted in the presence of an alcohol or aldehyde and hydrogen on hydrogenation catalysts.

Catalytic hydrogenation with frustrated lewis pairs: Selectivity achieved by size-exclusion design of lewis acids

Catalytic hydrogenation that utilizes frustrated Lewis pair (FLP) catalysts is a subject of growing interest because such catalysts offer a unique opportunity for the development of transition-metal-free hydrogenations. The aim of our recent efforts is to further increase the functional-group tolerance and chemoselectivity of FLP catalysts by means of size-exclusion catalyst design. Given that hydrogen molecule is the smallest molecule, our modified Lewis acids feature a highly shielded boron center that still allows the cleavage of the hydrogen but avoids undesirable FLP reactivity by simple physical constraint. As a result, greater latitude in substrate scope can be achieved, as exemplified by the chemoselective reduction of α,β-unsaturated imines, ketones, and quinolines. In addition to synthetic aspects, detailed NMR spectroscopic, DFT, and 2H isotopic labeling studies were performed to gain further mechanistic insight into FLP hydrogenation. Copyright

PROCESS FOR PREPARING UNSYMMETRIC SECONDARY TERT-BUTYLAMINES IN THE LIQUID PHASE

The present application relates to a process for preparing unsymmetric secondary tert-butylamines which, as well as the tert-butyl radical, also comprise an alkyl, cycloalkyl or benzyl radical. They are prepared by reacting corresponding aldehydes with tert-butylamine and hydrogen in the presence of hydrogenation catalysts (reductive amination) in the liquid phase.

PROCESS FOR PREPARING UNSYMMETRIC SECONDARY TERT-BUTYLAMINES IN THE GAS PHASE

The present invention relates to a process for preparing unsymmetric secondary tert-butylamines by continuous amination in the gas phase, wherein tert-butylamine is converted over hydrogenation catalysts in the presence of an alcohol or aldehyde and hydrogen.

ELECTROCHEMICAL REDUCTIVE AMINATION. II. AMINATION OF ALIPHATIC ALDEHYDES WITH PRIMARY AMINES

The formation of a secondary amine by the electrolysis of an aqueous solution containing an aldehyde and a primary amine was studied.The formation of the secondary amines passes through the intermediate stage of an aldimine.The highest yield of secondary amine is attained at a molar ratio of primary amine to aldehyde of 1.2:1.As electrode material lead, cadmium, zinc, and copper may be used.As supporting electrolyte a phosphate buffer with a pH close to the pKa of the primary amine is recommended.By the method developed 32 amines with various structures were synthesized.

PHOSPHONIUM DIAZA-DIYLIDS AND AZA-YLDIID AS NEW AND EFFICIENT REAGENTS FOR PRIMARY AND SECONDARY AMINES SYNTHESIS

Metallated aminophosphonium ylids, diaza-diylids and aza-yldiid, are investigated as reagents for primary and secondary amines synthesis.