6911-87-1

Usage

Chemical Properties

colorless to dark purple-brown liquid

InChI:InChI=1/C7H8BrN/c1-9-7-4-2-6(8)3-5-7/h2-5,9H,1H3

Upstream product

• 614-00-6 N-methyl-N-nitrosoaniline 
• 579-10-2 N-acetyl-N-methylaniline 
• 79-08-3 bromoacetic acid 
• 77-78-1 dimethyl sulfate 
• 106-40-1 4-bromo-aniline 
• 937-23-5 4-bromo-N-nitroso-N-methylaniline 
• 100-61-8 N-methylaniline 
• 50-00-0 formaldehyd 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 2617-78-9 N-(4-bromophenyl)formamide 
• 74763-65-8 1,4-Bis(p-bromophenyl)-1,4-dimethyl-2-tetrazene 
• 117896-63-6 (4-Bromo-phenyl)-tert-butylperoxymethyl-methyl-amine 
• 107047-10-9 p-bromobenzylazide 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 100716-00-5 N-(4-bromo-phenyl)-N-methyl-N'-phenyl-urea 
• 87010-84-2 N₁-methyl-N₁-p-bromophenyl-N₂-phenylbenzamidine 
• 99359-26-9 N-allyl-4-bromo-N-methylaniline 
• 87010-90-0 N₁-methyl-N₁,N₂-di-p-bromophenylbenzamidine 
• 116331-82-9 C₁₃H₁₁BrFN₃ 
• 87010-87-5 N₁-methyl-N₁-p-bromophenyl-N₂-m-methoxyphenylbenzamidine 
• 93680-43-4 C₈H₈BrN₇ 
• 99942-80-0 N,N'-Bis-(4-bromo-phenyl)-N-methyl-acetamidine 
• 110994-03-1 N-(4-Bromo-phenyl)-N-methyl-S-trimethylsilanylethynyl-thiohydroxylamine 
• 23042-33-3 4-bromo-N-methyl-N-nitro-aniline 
• 102235-84-7 4'-Brom-2-chlor-N-methylacetanilid 
• 182871-21-2 (4-Bromo-phenyl)-cyclohex-2-enyl-methyl-amine 
• 937-23-5 4-bromo-N-nitroso-N-methylaniline 
• 282107-78-2 Bis(diethylamino)-4-[N-bis(diethylamino)phosphino-N-methylamino]phenylphosphonite 

Relevant academic research and scientific papers

Electronically tuneable orthometalated RuII–NHC complexes as efficient catalysts for C–C and C–N bond formations via borrowing hydrogen strategy

The catalytic activities of a series of simple and electronically tuneable cyclometalated RuII–NHC complexes (2a–d) were explored in various C–C/N bond formations following the borrowing hydrogen process. Slight modifications in the ligand backbone were noted to tune the activities of these complexes. Among them, the complex 2d featuring a 1,2,4-triazolylidene donor with a 4-NO2–phenyl substituent displayed the highest activity for the coupling of diverse secondary and primary alcohols with a low catalyst loading of 0.01 mol% and a sub-stoichiometric amount of inexpensive KOH base. The efficacy of this simple system was further showcased in the challenging one-pot unsymmetrical double alkylation of secondary alcohols using different primary alcohols. Moreover, the complex 2d also effectively catalyses the selective mono-N-methylation of various aromatic and aliphatic primary amines using methanol to deliver a range of N-methyl amines. Mechanistically, the β-alkylation reaction follows a borrowing hydrogen pathway which was established by the deuterium labelling experiment in combination with various control experiments. Intriguingly, in situ1H NMR and ESI-MS analyses evidently suggested the involvement of a Ru–H species in the catalytic cycle and further, the kinetic studies revealed a first order dependence of the reaction rate on the catalyst as well as the alcohol concentrations.

Nanosized CdS as a Reusable Photocatalyst: The Study of Different Reaction Pathways between Tertiary Amines and Aryl Sulfonyl Chlorides through Visible-Light-Induced N-Dealkylation and C-H Activation Processes

It has been found that the final products of the reaction of sulfonyl chlorides and tertiary amines in the presence of cadmium sulfide nanoparticles under visible light irradiation are highly dependent on the applied reaction conditions. Interestingly, with the change of a reaction condition, different pathways were conducted (visible-light-induced N-dealkylation or sp3 and sp2 C-H activation) that lead to different products such as secondary amines and various sulfonyl compounds. Remarkably, all of these reactions were performed under visible light irradiation and an air atmosphere without any additive or oxidant in benign solvents or under solvent-free conditions. During this study, the CdS nanoparticles as affordable, heterogeneous, and recyclable photocatalysts were designed, successfully synthesized, and fully characterized and applied for these protocols. During these studies, intermediates resulting from the oxidation of tertiary amines are trapped during the photoinduced electron transfer (PET) process. The reaction was carried out efficiently with a variety of substrates to give the corresponding products at relatively short times in good to excellent yields in parallel with the use of the visible light irradiation as a renewable energy source. Most of these processes are novel or are superior in terms of cost-effectiveness, safety, and simplicity to published reports.

Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2

We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO2.

Biobased Spiroimides from Itaconic Acid and Formamides: Molecular Targets for a Novel Synthetic Application of Renewable Chemicals

Spiroimides exhibit a wide range of biological activities, such as anticonvulsant, antiarrhythmic, and antihyperglycemic activities. Herein, a novel synthetic application of renewable chemicals, itaconic acid and formamides, is described. Proper exploitation of the reactivity of itaconic acid and formamide allows for the development of an efficient synthetic approach for the production of several new biobased spiroimides, spiro[dihydroquinolin-2-one-succinimides] and spiro[indolin-2-one-glutarimides], in excellent overall yields (up to 98%).

Visible light-induced mono-bromination of arenes with BrCCl3

A highly efficient and regioselective bromination of electron-rich arenes and heteroarenes using commercially available BrCCl3as a “Br” source has been developed. The reaction was performed in air under mild conditions with photocatalyst Ru(bpy)3Cl2·6H2O, avoiding the usage of strong acids and strong oxidants. Mono-brominated products were obtained with medium to excellent yields (up to 94%). This strategy has shown good compatibility and highpara-selectivity, which will facilitate the complicated synthesis.

CO2-tuned highly selective reduction of formamides to the corresponding methylamines

We herein describe an efficient, CO2-tuned and highly selective C-O bond cleavage of N-methylated formanilides. With easy-to-handle and commercially available NaBH4 as the reductant, a variety of formanilides could be turned into the desired tertiary amines in moderate to excellent yields. The role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments.

A nonheme peroxo-diiron(iii) complex exhibiting both nucleophilic and electrophilic oxidation of organic substrates

The complex [FeIII2(μ-O2)(L3)4(S)2]4+(L3= 2-(4-thiazolyl)benzimidazole, S = solvent) forms upon reaction of [FeII(L3)2] with H2O2and is a functional model of peroxo-diiron intermediates invoked during the catalytic cycle of oxidoreductases. The spectroscopic properties of the complex are in line with those of complexes formed with N-donor ligands. [FeIII2(μ-O2)(L3)4(S)2]4+shows both nucleophilic (aldehydes) and electrophilic (phenol,N,N-dimethylanilines) oxidative reactivity and unusually also electron transfer oxidation.

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.

Additive-freeN-methylation of amines with methanol over supported iridium catalyst

An efficient and versatile zinc oxide-supported iridium (Ir/ZnO) catalyst was developed to catalyze the additive-freeN-methylation of amines with methanol. Mechanistic studies suggested that the high catalytic reactivity is rooted in the small sizes (1.4 nm) of Ir nanoparticles and the high ratio (93%) of oxidized iridium species (IrOx, Ir3+and Ir4+) on the catalyst. Moreover, the delicate cooperation between the IrOxand ZnO support also promoted its high reactivity. The selectivity of this catalyticN-methylation was controllable between dimethylation and monomethylation by carefully tuning the catalyst loading and reaction solvent. Specifically, neat methanol with high catalyst loading (2 mol% Ir) favored the formation ofN,N-dimethylated amine, while the mesitylene/methanol mixture with low catalyst loading (0.5 mol% Ir) was prone to producing mono-N-methylated amines. An environmentally benign continuous flow system with a recycled mode was also developed for the efficient production ofN-methylated amines. With optimal flow rates and amine concentrations, a variety ofN-methylamines were produced with good to excellent yields in this Ir/ZnO-based flow system, providing a starting point for the clean and efficient production ofN-methylamines with this cost-effective chemical process.

Enantioconvergent and Regioselective Synthesis of Allenylsilanes by Nickel-Catalyzed C(sp2)-C(sp3) Cross-Coupling Starting from Racemic α-Silylated Propargylic Bromides

A direct synthesis of enantioenriched allenylsilanes from racemic α-silylated propargylic bromides by an enantioconvergent nickel-catalyzed cross-coupling is reported. The high regioselectivity is governed by the bulky silyl group, and the C(sp2)-C(sp3) bond formation occurs exclusively at the γ-position of the propargyl electrophile. The level of enantioselection induced by a chiral Pybox ligand is moderate.