136295-03-9

Basic information

• Product Name: N-phenyl-α,α-dideuteriobenzenemethanamine
• Synonyms: N-phenyl-α,α-dideuteriobenzenemethanamine
• CAS NO: 136295-03-9
• Molecular Weight: 185.237
• Mol File: 136295-03-9.mol

Chemical Properties

• CAS DataBase Reference: N-phenyl-α,α-dideuteriobenzenemethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-phenyl-α,α-dideuteriobenzenemethanamine(136295-03-9)
• EPA Substance Registry System: N-phenyl-α,α-dideuteriobenzenemethanamine(136295-03-9)

Safety Data

• Hazardous Substances Data: 136295-03-9(Hazardous Substances Data)

Upstream product

• 21175-64-4 1,1-dideuteriophenylmethanol 
• 538-51-2 benzylidene phenylamine 
• 62-53-3 aniline 
• 100-51-6 benzyl alcohol 
• 614-30-2 N-methyl-N-phenyl-benzenemethanamine 
• 100-39-0 benzyl bromide 
• 100-61-8 N-methylaniline 
• 100-52-7 benzaldehyde 
• 758640-21-0 N-Benzylaniline 
• 71258-23-6 benzyl alcohol-d7 
• 587-03-1 3-methylbenzyl alcohol 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 93-98-1 N-phenyl benzoyl amide 
• 1624-55-1 α-D-trans-N-benzylideneaniline 

Relevant articles and documents

Mechanistic investigations on the reaction between amines or amides and an alkylperoxy-λ3-iodane

A mechanism involving the intermediate formation of an amine radical cation by single-electron transfer is proposed for the oxidation of secondary amines with alkylperoxy-λ3-iodane. On the other hand, the oxidation of acetamides probably proceeds by a radical process, which involves the direct hydrogen abstraction of the methylene group α to the nitrogen atom.

N-Alkylation of Amines with Alcohols Catalyzed by Manganese(II) Chloride or Bromopentacarbonylmanganese(I)

A manganese-catalyzed N-alkylation reaction of amines with alcohols via hydrogen autotransfer strategy has been demonstrated. The developed practical catalytic system including an inexpensive, nontoxic, commercially available MnCl2 or MnBr(CO)5 as the metal salt and triphenylphosphine as a ligand provides access to diverse aromatic, heteroaromatic, and aliphatic secondary amines in moderate-to-high yields. In addition, this operationally simple protocol is scalable to the gram level and suitable for synthesizing heterocycles such as indole and resveratrol-derived amines known to be active for Alzheimer's disease.

Ruthenium(ii) complexes with N-heterocyclic carbene-phosphine ligands for theN-alkylation of amines with alcohols

Metal hydride complexes are key intermediates forN-alkylation of amines with alcohols by the borrowing hydrogen/hydrogen autotransfer (BH/HA) strategy. Reactivity tuning of metal hydride complexes could adjust the dehydrogenation of alcohols and the hydrogenation of imines. Herein we report ruthenium(ii) complexes with hetero-bidentate N-heterocyclic carbene (NHC)-phosphine ligands, which realize smart pathway selection in theN-alkylated reactionviareactivity tuning of [Ru-H] species by hetero-bidentate ligands. In particular, complex6cbwith a phenyl wingtip group and BArF?counter anion, is shown to be one of the most efficient pre-catalysts for this transformation (temperature is as low as 70 °C, neat conditions and catalyst loading is as low as 0.25 mol%). A large variety of (hetero)aromatic amines and primary alcohols were efficiently converted into mono-N-alkylated amines in good to excellent isolated yields. Notably, aliphatic amines, challenging methanol and diamines could also be transformed into the desired products. Detailed control experiments and density functional theory (DFT) calculations provide insights to understand the mechanism and the smart pathway selectionvia[Ru-H] species in this process.

Enhanced Hydride Donation Achieved Molybdenum Catalyzed Direct N-Alkylation of Anilines or Nitroarenes with Alcohols: From Computational Design to Experiment

An example of homogeneous Mo-catalyzed direct N-alkylation of anilines or nitroarenes with alcohols is presented. The DFT aimed design suggested the easily accessible bis-NHC-Mo(0) complex features a strong hydride-donating ability, achieving effective N-alkylation of anilines or challenging nitroarenes with alcohols. The enhanced hydride-donating strategy should be useful in designing highly active systems for borrowing hydrogen transformations.

Convenient and Reusable Manganese-Based Nanocatalyst for Amination of Alcohols

The development of new sustainable nanocatalytic systems for green chemical synthesis is a growing area in chemical science. Herein, a reusable heterogeneous N-doped graphene-based manganese nanocatalyst (Mn@NrGO) for selective N-alkylation of amines with alcohols is described. Mechanistic studies illustrate that the catalytic reaction follows a domino dehydrogenation-condensation-hydrogenation sequence of alcohols and amines with the formation of water as the sole by-product. The scope of the reaction is extended to the synthesis of pharmaceutically important N-alkylated amine intermediates. The heterogeneous nature of the catalyst made it easy to separate for long-term performance, and the recycling study revealed that the catalyst was robust and retained its activity after several recycling experiments.

A Fe single atom on N,S-doped carbon catalyst for performing N-alkylation of aromatic amines under solvent-free conditions

A green and gram-scale strategy has been developed for the synthesis of Fe single atom/N,S-doped carbon catalyst (Fe20-SA@NSC) via the pyrolysis of polyaniline (PAN)-modified Fe,S-doped ZIFs, in which the synthesis of ZIFs can be accomplished in water at room temperature. The as-prepared catalyst exhibits superior activity in the N-alkylation of amines with alcohols via a borrowing strategy under solvent-free conditions (TOF up to 13.9 h-1). Based on the HAADF-STEM and XAFS results, Fe in this material is dispersed as the single-atom Fe1-N4S1 site. According to the experimental and theoretical calculation results, the Fe1-N4S1 site displays a better borrowing hydrogen ability than other Fe sites owing to its higher electron density. In addition, this catalyst has excellent stability and recyclability, and no obvious loss in activity is observed after 7 runs.

Pyridine mediated transition-metal-free direct alkylation of anilines using alcohols: via borrowing hydrogen conditions

Herein, we report pyridine and other similar azaaromatics as efficient biomimetic hydrogen shuttles for a transition-metal-free direct N-alkylation of aryl and heteroaryl amines using a variety of benzylic and straight chain alcohols. Mechanistic studies including deuterium labeling and the isolation of dihydro-intermediates of the benzannulated pyridine confirmed the role of pyridine and a borrowing hydrogen process operating in these reactions. In addition, we have extended this methodology for the development of dehydrogenative synthesis of quinolines and indoles, as well as the transfer hydrogenation of ketones. This journal is

Regioselective, Photocatalytic α-Functionalization of Amines

Photocatalytic α-functionalization of amines provides a mild and atom-economical means to synthesize α-branched amines. Prior examples featured symmetrical or electronically biased substrates. Here we report a controllable α-functionalization of amines in which regioselectivity can be tuned with minor changes to the reaction conditions.

A nanoscale iron catalyst for heterogeneous direct: N - And C -alkylations of anilines and ketones using alcohols under hydrogen autotransfer conditions

Here, we report a commercially available nanoscale Fe catalyst for heterogeneous direct N- and C-alkylation reactions of anilines and methyl ketones with alcohols. A hydrogen autotransfer mechanism has been found to operate in these reactions by deuterium labelling studies. In addition, dehydrogenative quinoline synthesis has been demonstrated from amino benzyl alcohols and acetophenones.

Borrowing Hydrogen-Mediated N-Alkylation Reactions by a Well-Defined Homogeneous Nickel Catalyst

We report herein a well-defined and bench-stable azo-phenolate ligand-coordinated nickel catalyst which can efficiently execute N-alkylation of a variety of anilines by alcohol. We demonstrate that the redox-active azo ligand can store hydrogen generated during alcohol oxidation and redelivers the same to an in-situ-generated imine bond to result in N-alkylation of amines. The reaction has wide scope, and a large array of alcohols can directly couple to a variety of anilines. Mechanistic studies including deuterium labeling to the substrate establishes the borrowing hydrogen method from alcohols and pinpoints the crucial role of the redox-active azo moiety present on the ligand backbone. Isolation of the ketyl intermediate in its trapped form with a radical quencher and higher kH/kD for the alcohol oxidation step suggest altogether a hydrogen-atom transfer (HAT) to the reduced azo backbone to pave alcohol oxidation as opposed to the conventional metal-ligand bifunctional mechanism. This example clearly demonstrates that an inexpensive base metal catalyst can accomplish an important coupling reaction with the help of a redox-active ligand backbone.