2909-79-7

Usage

Uses

Used in Polymer Industry:
4-TERT-BUTYL-N,N-DIMETHYLANILINE is used as an amine initiator for free-radical/cationic hybrid photopolymerizations of acrylates and epoxides. Its application reason is to enhance the polymerization process, leading to improved efficiency and product quality in the production of various polymers.
Used in Chemical Research:
In the field of chemical research, 4-TERT-BUTYL-N,N-DIMETHYLANILINE is used as a catalyst in the oxidative coupling of tert-butyl-N,N-dimethylaniline with indole. This process is significant for the synthesis of various complex organic compounds and contributes to the advancement of chemical knowledge and innovation.

InChI:InChI=1/C12H19N/c1-12(2,3)10-6-8-11(9-7-10)13(4)5/h6-9H,1-5H3

Upstream product

• 67-56-1 methanol 
• 769-92-6 4-tert-Butylaniline 
• 77-78-1 dimethyl sulfate 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 1067-24-9 dimethylamino tributyltin 
• 67530-30-7 N,N-dimethyl O-(2,4,6-trimethylphenyl-sulfonyl) hydroxylamine 
• 63488-10-8 4-tert-butylmagnesium bromide 
• 50-00-0 formaldehyd 
• 3282-56-2 4-tert-butylnitrobenzene 
• 67-68-5 dimethyl sulfoxide 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 677-22-5 tert-butylmagnesium chloride 
• 3972-56-3 4-(tert-butyl)chlorobenzene 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 5279-59-4 4-(1,1-dimethylethyl)-N-methylbenzenamine 
• 98757-38-1 (dicarbonyl)(cyclopentadienyl)(trimethylphosphine)tungsten hydride 
• 321358-86-5 4-tert-butyl-N,N-dimethylanilinium tetrafluoroborate 
• 1072197-64-8 4-(tert-butyl)-N,N-dimethylaniline N-oxide 
• 1179825-64-9 2-(((4-tert-butylphenyl)(methyl)amino)methyl)cyclohexan-1-one 
• 1179825-49-0 1-((4-tert-butylphenyl)(methyl)amino)-4,4-dimethylpentan-3-one 
• 1268830-98-3 3-(((4-tert-butylphenyl)(methyl)amino)methyl)indolizine-1-carbonitrile 
• 1314535-68-6 6-tert-butyl-1-methyl-3-phenyl-2,3-dihydroquinoline-4,4(1H)-dicarbonitrile 
• 1346855-02-4 1-(5-tert-butyl-2-(dimethylamino)phenyl)naphthalen-2-ol 
• 1415753-73-9 C₂₁H₂₄N₂O 
• 1417627-95-2 2-(1-(4-(tert-butyl)phenyl)-2-((4-(tert-butyl)phenyl)(methyl)amino)ethyl)malononitrile 
• 1417627-94-1 2-(2-((4-(tert-butyl)phenyl)(methyl)amino)-1-(o-tolyl)ethyl)malononitrile 
• 1417627-78-1 6-(tert-butyl)-1-methyl-3-(o-tolyl)-2,3-dihydroquinoline-4,4(1H)-dicarbonitrile 
• 1417627-93-0 2-(2-((4-(tert-butyl)phenyl)(methyl)amino)-1-(2,4-dimethylphenyl)ethyl)malononitrile 

Relevant academic research and scientific papers

Method for realizing N-alkylation by using alcohols as carbon source under photocatalysis

The invention discloses a method for realizing N-alkylation by using alcohols as a carbon source under photocatalysis, and belongs to the technical field of catalytic synthesis. Alcohol, a substrate raw material and a catalyst are placed in a reaction device, ultraviolet and/or visible light irradiation is carried out in an inert atmosphere, after the irradiation is finished, solid-liquid separation is carried out to remove the catalyst, and an N-alkylation product can be obtained through extraction, distillation and purification, wherein the substrate raw material comprises any one of an amine compound, an aromatic nitro compound or an aromatic nitrile compound, the alcohol comprises any one or more of soluble primary alcohols, and the catalyst is metal oxide/titanium dioxide or metal sulfide/titanium dioxide. The method is simple and easy to operate, can be used for efficient photocatalysis one-pot multi-step hydrogenation N-alkylation reaction, and is mild in reaction condition, high in chemical selectivity of N-alkylamine, good in catalyst stability and easy to recycle.

Nickel-Catalyzed Amination of Aryl Chlorides with Amides

A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.

Fe(III)-catalyzed Oxidative Povarov Reaction with Molecular Oxygen Oxidant

The synthesis of tetrahydroquinoline derivatives from dimethyl anilines and enamides has been developed by Fe(III)-phenanthroline complex under aerobic condition. The oxidation of tertiary anilines involving a single electron transfer of Fe(phen)3(PF6)3 afforded the iminium ion intermediate, which reacted with electron-rich alkenes to build a six-membered N-heterocycles containing quaternary carbon center via the oxidative Povarov reaction process.

Aminomethylation of Aryl Bromides by Nickel-Catalyzed Electrochemical Redox Neutral Cross Coupling

We develop an electrochemical nickel-catalyzed aminomethylation of aryl bromides under mild conditions. The convergent paired electrolysis makes full use of anode and cathode processes, free of a terminal oxidant, a sacrificial anode, a metal reductant, and a prefunctionalized radical precursor. In addition, this method exhibits wide functional group tolerance (63 examples), including some sensitive substituents and aromatic heterocycles. This redox neutral cross coupling provides a more environmentally friendly and synthetic practical protocol for forging C(sp2)–C(sp3) bonds.

Redox-Selective Iron Catalysis for α-Amino C-H Bond Functionalization via Aerobic Oxidation

Single-electron oxidation and α-deprotonation of tertiary anilines using Fe(phen)3(PF6)3 afford α-aminoalkyl radicals, which can be coupled with electrophilic partners to afford various tetrahydroquinolines. Mechanistically, the Fe(phen)n 2+/3+ catalytic cycle is maintained by O2 or a TBHP oxidant, and the presence of the oxygen bound iron complex, Fe(III)-OO(H), was elucidated by electron paramagnetic resonance and electrospray ionization mass spectrometry. This redox-selective nonheme iron catalyst behaves similarly to bioinspired heme iron catalysts.

A Highly Selective Palladium-Catalyzed Aerobic Oxidative Aniline-Aniline Cross-Coupling Reaction

The first catalytic oxidative aniline-aniline cross-coupling reaction using oxygen as the terminal oxidant is reported. Anilines possessing a pyrrolidino group can be preferentially oxidized under mild aerobic conditions and reacted with other anilines to afford a variety of nonsymmetrical 2-aminobiphenyls with high selectivities. A heterogeneous palladium catalyst is used for the dehydrogenative cross-coupling of anilines with structurally diverse arenes. This reaction does not require stoichiometric oxidants and is an economical and environmentally friendly method.

Photorearrangement of Quinoline-Protected Dialkylanilines and the Photorelease of Aniline-Containing Biological Effectors

The direct release of dialkylanilines was achieved by controlling the outcome of a photorearrangement reaction promoted by the (8-cyano-7-hydroxyquinolin-2-yl)methyl (CyHQ) photoremovable protecting group. The substrate scope was investigated to obtain structure-activity relationships and to propose a reaction mechanism. Introducing a methyl substituent at the 2-methyl position of the CyHQ core enabled the bypass of the photorearrangement and significantly improved the aniline release efficiency. We successfully applied the strategy to the photoactivation of mifepristone (RU-486), an antiprogestin drug that is also used to induce the LexPR gene expression system in zebrafish and the gene-switch regulatory system based on the pGL-VP chimeric regulator in mammals.

An N-heterocyclic carbene-based nickel catalyst for the Kumada–Tamao–Corriu coupling of aryl bromides and tertiary alkyl Grignard reagents

In this study, nickel-catalyzed coupling reactions between arylhalides and tert-alkyl Grignard reagents were developed. Our original bicyclic NHC ligands reduced the formation of isomerized products, and we found that NMP as a co-solvent suppressed the reduction process. Under the optimal conditions we developed, the catalyst loading was lowered to 0.5?mol?%, and catalyst loading using ortho-substituted aryl bromides was also applicable at the level of 2.0?mol?%.

Reductive Umpolung of Carbonyl Derivatives with Visible-Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α-Amino Radicals and Ketyl Radicals

Visible-light-mediated photoredox-catalyzed aldimine-aniline and aldehyde-aniline couplings have been realized. The reductive single electron transfer (SET) umpolung of various carbonyl derivatives enabled the generation of intermediary ketyl and α-amino radical anions, which were utilized for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols. Anilines can be coupled with aldimines or aldehydes in a visible-light-mediated photoredox-catalyzed process. Reductive single electron transfer (SET) umpolung of the carbonyl derivatives leads to the generation of intermediary ketyl and α-amino radical anions, which were used for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols.

Base-oxidant promoted metal-free N-demethylation of arylamines

A metal-free oxidative N-demethylation of arylamines with triethylamine as a base and tert-butyl hydroperoxide (TBHP) as oxidant is reported in this paper. The reaction is general, practical, inexpensive, non-toxic, and the method followed is environmentally benign, with moderate to good yields. [Figure not available: see fulltext.]