87385-38-4

Usage

Uses

Used in Chemical Research:
N,N-DIMETHYLANILINE-2,3,4,5,6-D5 is used as a research compound for chemical studies. The incorporation of deuterium atoms allows for the investigation of reaction mechanisms, kinetics, and the behavior of the molecule under various conditions. This is particularly useful in studying the effects of isotopic substitution on chemical properties and reactivity.
Used in Biochemical Research:
In the field of biochemistry, N,N-DIMETHYLANILINE-2,3,4,5,6-D5 serves as a valuable tool for studying enzyme interactions and metabolic pathways. The deuterium labeling can help in elucidating the binding sites and mechanisms of enzymes, as well as in tracking the molecule's behavior within biological systems.
Used in Analytical Chemistry:
N,N-DIMETHYLANILINE-2,3,4,5,6-D5 is utilized in analytical chemistry for the development and validation of analytical methods. The presence of deuterium atoms can enhance the detection and quantification of the compound using techniques such as mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy, providing more accurate and reliable results.
Used in Pharmaceutical Development:
In the pharmaceutical industry, N,N-DIMETHYLANILINE-2,3,4,5,6-D5 can be employed as a labeled analog of N,N-dimethylaniline for drug development studies. It can be used to investigate the pharmacokinetics, pharmacodynamics, and potential side effects of related drug candidates, contributing to the design of safer and more effective medications.
Used in Environmental Studies:
N,N-DIMETHYLANILINE-2,3,4,5,6-D5 can also be applied in environmental research to understand the fate and transport of similar organic compounds in the environment. The use of this isotopically labeled compound can provide insights into the degradation, bioaccumulation, and ecological impact of related chemicals.

Upstream product

• 121-69-7 N,N-dimethyl-aniline 
• 50-00-0 formaldehyd 
• 4165-61-1 aniline-d5 
• 865-50-9 iodomethane-d3 
• 74-88-4 methyl iodide 
• 1076-43-3 benzene-d6 

Downstream Products

• 51246-03-8 (E)-[β-D₁]-α-bromostyrene 
• 51246-19-6 (Z)-[β-D₁]-α-bromostyrene 

Relevant academic research and scientific papers

Efficient continuous-flow HD exchange reaction of aromatic nuclei in D2O/2-PrOH mixed solvent in a catalyst cartridge packed with platinum on carbon beads

Herein, a continuous-flow deuteration methodology for various aromatic compounds is developed based on heterogeneous platinum-catalyzed hydrogen-deuterium exchange. The reaction entails the transfer of a substrate dissolved in a mixed solvent of 2-propanol and deuterium oxide into a catalyst cartridge packed with platinum on carbon beads (Pt/CB). Pt/ CB could be continuously used without significant deterioration of catalyst activity for at least 24 h. Deuteration proceeded within 60 s of the substrate solutions being passed through the Pt/CB layer in the Pt/CB-packed cartridge.

Para-Selective C-H Olefination of Aniline Derivatives via Pd/S,O-Ligand Catalysis

Herein we report a highly para-selective C-H olefination of aniline derivatives by a Pd/S,O-ligand-based catalyst. The reaction proceeds under mild reaction conditions with high efficiency and broad substrate scope, including mono-, di-, and trisubstituted tertiary, secondary, and primary anilines. The S,O-ligand is responsible for the dramatic improvements in substrate scope and the high para-selectivity observed. This methodology is operationally simple, scalable, and can be performed under aerobic conditions.

Oxidative Cyclization Synthesis of Tetrahydroquinolines and Reductive Hydrogenation of Maleimides under Redox-Neutral Conditions

A redox-neutral reaction without using any external oxidant and reductant in one pot is described. By combining a Ru(bpy)32+ photocatalyst and cobaloxime catalyst, a number of tertiary anilines can be oxidized by Ru(bpy)3

Metal-free regioselective hydrobromination of alkynes through CH/CBr activation

A metal-free regioselective hydrobromination of alkynes has been developed to provide the Markovnikov-type vinyl bromides in good yields using dibromomethane/N,N-dimethylaniline as in-situ 'HBr' source. This protocol also represents an elegant example of the activation of sp2 CH and CBr bonds in one pot, in which 'HBr' is generated and transferred under mild metal-free conditions. D-incorporated experiments were employed to investigate the reaction mechanism and a plausible reaction path was proposed.

Catalytic arene H/D exchange with novel rhodium and iridium complexes

Three novel pendant acetate complexes, [Rh(bdmpza)Cl3] -M+, [Rh(bdmpza)Cl2(py)], and [Ir(bdmpza)Cl3]-M+ (bdmpza = bis(3,5-dimethylpyrazol-1-yl) acetate, M+ = Li+, Na +), were synthesized. Abstraction of halide from these complexes with silver salts yielded species capable of C-H activation of arenes. The catalytic H/D exchange reaction between benzene and trifluoroacetic acid-d was optimized, and these conditions were used to evaluate H/D exchange in other arenes. Branched alkyl substituents in alkyl aromatics showed an affinity toward deuterium exchange in the β-alkyl position only. DFT calculations were performed to determine the mechanism of H/D exchange.

Efficient and selective Pt/C-catalyzed H-D exchange reaction of aromatic rings

An effective and applicable deuteration method for aromatic rings using Pt/C-D2O-H2 system was established. Especially, phenol was fully deuterated even at room temperature, and other electron-rich aromatic nuclei were efficiently deuterated under mild conditions. The scope and limitations of the presence method and its application to the synthesis of deuterium-labeled biologically active compounds and deuterium-labeled building blocks for practical multi-gram scale syntheses are reported. 2008 The Chemical Society of Japan.