16518-62-0

Usage

Uses

Used in Organic Synthesis:
3-Bromo-N,N-dimethylaniline is used as a chemical intermediate for the synthesis of other organic compounds. Its reactivity and functional groups make it a valuable building block in the preparation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Fluorination Reactions:
In the field of fluorochemistry, 3-Bromo-N,N-dimethylaniline is utilized in fluorination processes, where it is converted to 3-fluoro-N,N-dimethylaniline. This transformation is achieved using metal fluoride in the presence of a 2-(di-1-adamantylphosphino)-3,6-dimethoxy-2',4',6'-tri-i-propyl-1,1'-biphenyl (AdBrettPhos)-based Pd precatalyst. The resulting 3-fluoro-N,N-dimethylaniline is an important compound for further chemical modifications and applications in various industries.
Used in Pharmaceutical Industry:
3-Bromo-N,N-dimethylaniline plays a crucial role in the pharmaceutical industry, where it serves as a key intermediate in the synthesis of various drug molecules. Its unique structure allows for the development of new drugs with specific therapeutic properties, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Bromo-N,N-dimethylaniline is employed as a precursor for the production of pesticides and other crop protection agents. Its involvement in the synthesis of these compounds helps to ensure the development of effective and targeted solutions for agricultural challenges.
Overall, 3-Bromo-N,N-dimethylaniline is a versatile compound with applications across multiple industries, primarily due to its role as a chemical intermediate in the synthesis of a wide range of products.

InChI:InChI=1/C8H10BrN/c1-10(2)8-5-3-4-7(9)6-8/h3-6H,1-2H3

Upstream product

• 77-78-1 dimethyl sulfate 
• 591-19-5 m-Bromoaniline 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 75-07-0 acetaldehyde 
• 64-19-7 acetic acid 
• 74-88-4 methyl iodide 
• 512-56-1 trimethyl phosphite 
• 585-79-5 m-nitrobromobenzene 
• 62-53-3 aniline 

Downstream Products

• 17405-06-0 N-(3-bromophenyl)-N-methylnitrous amide 
• 99-64-9 3-(dimethylamino)benzoic acid 
• 63594-70-7 4,4'-methylenebis 
• 33284-28-5 3-dimethylaminobenzenethio 
• 60469-89-8 4-dimethylamino-o-dibromobenzene 
• 17961-91-0 3-dimethylaminophenyl-trimethylsilane 
• 857725-94-1 3-bromo-N,N-dimethyl-4-nitroso-aniline 
• 18840-18-1 ph3Si(ph-3-Nme₂) 
• 53104-13-5 N-tert-Butyl-N-(3-dimethylamino-phenyl)-hydroxylamine 
• 33284-23-0 2,2,2-trifluoro-1-(3-dimethylaminophenyl)ethanone 
• 94026-68-3 7-(3-Dimethylamino-phenyl)-tropiliden 
• 98482-16-7 3-bromophenyl-3'-dimethylaminophenylmethylcarbinol 
• 55875-47-3 2-bromo-4-(dimethylamino)benzaldehyde 
• 73177-36-3 <3-(Dimethylamino)phenyl>acetone 

Relevant academic research and scientific papers

Synthesis and application of a ratiometric probe for hydrogen peroxide

Molecular imaging of biological analytes provides detailed insights into signaling processes. Ratiometric probes are particularly attractive due to the ability to quantify analyte production. However, design strategies for ratiometric probes can be hinder

Asymmetric bismuth-rhodamines as an activatable fluorogenic photosensitizer

Bismuth-rhodamine compounds stand out for their unique excitable photosensitizing properties and concomitant fluorescence; however, further knowledge of the structure-property relationship is required to expand the scope of their practical application. Wi

Photoresponsive transformation from spherical to nanotubular assemblies: Anticancer drug delivery using macrocyclic cationic gemini amphiphiles

We developed NIR-light-responsive macrocyclic cationic gemini amphiphiles, one of which displayed various favorable properties of lipids. The NIR-light-mediated cleavage of the strained dioxacycloundecine ring led to the conversion of the spherical to a n

m-(N,N,N,-trimethylammonio)trifluoroacetophenone: A femtomolar inhibitor of acetylcholinesterase

m-(N,N,N,-Trimethylammonio)trifluoroacetophenone is a potent, reversible, time-dependent inhibitor of acetylcholinesterases. The respective second-order rate constants (kon) for binding of the ketone to enzymes from Electrophorus electricus and

A design concept of long-wavelength fluorescent analogs of rhodamine dyes: Replacement of oxygen with silicon atom

Replacement of the oxygen with a silicon atom on the rhodamine framework produces a strong red-emission fluorophore which has a high molar extinction coefficient and 90 nm red shift relative to rhodamine dye PY. The Royal Society of Chemistry.

Trialkylammonium salt degradation: Implications for methylation and cross-coupling

Trialkylammonium (most notably N,N,N-trimethylanilinium) salts are known to display dual reactivity through both the aryl group and the N-methyl groups. These salts have thus been widely applied in cross-coupling, aryl etherification, fluorine radiolabelling, phase-transfer catalysis, supramolecular recognition, polymer design, and (more recently) methylation. However, their application as electrophilic methylating reagents remains somewhat underexplored, and an understanding of their arylation versus methylation reactivities is lacking. This study presents a mechanistic degradation analysis of N,N,N-trimethylanilinium salts and highlights the implications for synthetic applications of this important class of salts. Kinetic degradation studies, in both solid and solution phases, have delivered insights into the physical and chemical parameters affecting anilinium salt stability. 1H NMR kinetic analysis of salt degradation has evidenced thermal degradation to methyl iodide and the parent aniline, consistent with a closed-shell SN2-centred degradative pathway, and methyl iodide being the key reactive species in applied methylation procedures. Furthermore, the effect of halide and non-nucleophilic counterions on salt degradation has been investigated, along with deuterium isotope and solvent effects. New mechanistic insights have enabled the investigation of the use of trimethylanilinium salts in O-methylation and in improved cross-coupling strategies. Finally, detailed computational studies have helped highlight limitations in the current state-of-the-art of solvation modelling of reaction in which the bulk medium undergoes experimentally observable changes over the reaction timecourse. This journal is

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.

Silicon incorporation in polymethine dyes

Methods to red-shift fluorophores have garnered considerable interest due to the broad utility of low energy light. The incorporation of silicon into xanthene and coumarin scaffolds has resulted in an array of visible and near-infrared fluorophores. Here,

Synthesis of six-membered silacycles by borane-catalyzed double sila-Friedel-Crafts reaction

We have developed a catalytic synthetic method to prepare phenoxasilins. A borane-catalyzed double sila-Friedel-Crafts reaction between amino group-containing diaryl ethers and dihydrosilanes can be used to prepare a variety of phenoxasilin derivatives in

Synergistic catalysis of Cu+/Cu0 for efficient and selective N-methylation of nitroarenes with para-formaldehyde

In this paper, an inexpensive heterogeneous copper nanoparticles catalyst derived from CuAl-layered double hydroxide via an in situ topotactic transformation process was developed. Cu nanoparticles with uniform size were homogeneously dispersed on amorphous Al2O3 with strong metal-support interaction. Characterization results reveals that the Cu0 and Cu+ were simultaneously formed with Cu+ species as the dominant sites on the surface during the reduction process. The resultant catalyst Cu/Al2O3 demonstrates high catalytic activity, selectivity and durability for the reductive N-methylation of easily available nitroarenes in a cost-efficient, environmentally friendly and cascade manner. A broad spectrum of nitroarenes could be efficiently N-methylated to their corresponding N,N-dimethyl amines with good compatibility of various functional groups. The protocol is also applicable for the late-stage functionalization of biologically and pharmaceutically active nitro molecules. A structure-function relationship discloses that Cu0 and Cu+ sites on the surface pronouncedly boosts the reaction efficiency in a synergistic manner, in which Cu0 could facilitate H2 production and N-methylation of anilines, while Cu+ is considerably more active and participates in the overall process of the selective N-methylation of nitroarenes. Moreover, the catalyst also showed a strong stability and could be easily separated for successive reuses without an appreciable loss in activity and selectivity.