15185-02-1

Basic information

• Product Name: BENZYL-ALPHA,ALPHA-D2-AMINE
• Synonyms: BENZYL-ALPHA,ALPHA-D2-AMINE;Benzyl-α-α-D2-amine;Benzyl-a,a-d2-aMine
• CAS NO: 15185-02-1
• Molecular Formula: C₇H₉N
• Molecular Weight: 109.17
• Mol File: 15185-02-1.mol

Chemical Properties

• Boiling Point: 63-65 °C(Press: 20 Torr)
• Appearance: /
• CAS DataBase Reference: BENZYL-ALPHA,ALPHA-D2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL-ALPHA,ALPHA-D2-AMINE(15185-02-1)
• EPA Substance Registry System: BENZYL-ALPHA,ALPHA-D2-AMINE(15185-02-1)

Safety Data

• Hazardous Substances Data: 15185-02-1(Hazardous Substances Data)

Usage

Uses

Used in Research and Development:
BENZYL-ALPHA,ALPHA-D2-AMINE is used as an isotopically labeled compound for [application reason] in the field of research and development. The presence of deuterium atoms in the molecule allows researchers to study the effects of isotopic substitution on the compound's chemical and physical properties, as well as its interactions with other molecules and biological systems.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, BENZYL-ALPHA,ALPHA-D2-AMINE is used as a research compound for [application reason] in the development of new drugs and therapies. The isotopically labeled nature of the compound can help researchers understand the metabolic pathways and pharmacokinetics of similar molecules, ultimately leading to the design of more effective and safer drugs.
Used in Chemical Industry:
BENZYL-ALPHA,ALPHA-D2-AMINE is used as a labeled compound for [application reason] in the chemical industry. It can be employed in the synthesis of other isotopically labeled compounds, which can then be used in various applications, such as in the study of reaction mechanisms, catalysis, and the development of new materials.
Used in Environmental Science:
In environmental science, BENZYL-ALPHA,ALPHA-D2-AMINE is used as a tracer compound for [application reason] in the study of the fate and transport of pollutants in the environment. The use of isotopically labeled compounds allows researchers to track the movement and transformation of these pollutants in various environmental matrices, such as soil, water, and air.
Used in Analytical Chemistry:
BENZYL-ALPHA,ALPHA-D2-AMINE is used as a reference material for [application reason] in analytical chemistry. The compound can be used to calibrate and validate analytical instruments and methods, ensuring the accuracy and reliability of measurements in various fields, including pharmaceutical, chemical, and environmental analysis.

Upstream product

• 21175-64-4 1,1-dideuteriophenylmethanol 
• 93-89-0 benzoic acid ethyl ester 
• 51271-29-5 [1',1'-2H₂]benzyl bromide 
• 55-21-0 benzamide 
• 100-47-0 benzonitrile 

Downstream Products

• 1602983-00-5 C₂₁H₁₅⁽²⁾H₂NO₂ 
• 1602983-02-7 C₂₁H₁₆⁽²⁾HNO₂ 
• 780-25-6 N-benzylidene benzylamine 
• 3947-93-1 (N-deutero-phenyl-methylene)-aniline 
• 55-21-0 benzamide 
• 100-47-0 benzonitrile 
• 20002-22-6 dibenzylamine-α,α,α',α'-d4 
• 1370412-52-4 C₁₃H₁₂⁽²⁾H₂N₂ 
• 1384450-91-2 C₁₉H₁₇⁽²⁾HN₂ 
• 92204-13-2 phenylmethanamine-1,1-d₂-amine hydrochloride 

Relevant articles and documents

Preparation of deuteriated benzylamines and phenethylamine with Raney alloys in an alkaline deuterium oxide solution

Benzyl-α,α-2H2-amine, 2-2H1-Benzyl-α,α-2H2-amine, 3-2H1-Benzyl-α,α-2H2-amine, 4-2H1-Benzyl-α,α-2H2-am

Highly Selective Ruthenium-Catalyzed Direct Oxygenation of Amines to Amides

Reports on aerobic oxidation of amines to amides are rare, and those reported suffer from several limitations like poor yield or selectivity and make use of pure oxygen under elevated pressure. Herein, we report a practical and an efficient ruthenium-catalyzed synthetic protocol that enables selective oxidation of a broad range of primary aliphatic, heterocyclic and benzylic amines to their corresponding amides, using readily available reagents and ambient air as the sole oxidant. Secondary amines instead, yield benzamides selectively as the sole product. Mechanistic investigations reveal intermediacy of nitriles, which undergo hydration to afford amide as the final product.

Rhodium-Catalyzed Intramolecular C-H Bond Activation with Triazoles: Preparation of Stereodefined Pyrrolidines and Other Related Cyclic Compounds

On treatment of triazoles having an N-sulfonyl-protected benzylamine moiety with [Rh2(C7H15CO2)4], intramolecular C-H bond insertion takes place at the benzylic position to give cis-N-sulfonyl-2-aryl-3-[(sulfonylimino)methyl]pyrrolidines in good yields and with highly stereoselectivities. Analogously, the similar treatment of triazoles having an ether or even an alkyl moiety affords 2-alkyl- or 2-aryl-3-[(sulfonylimino)methyl]tetrahydrofurans or a 2-alkyl-3-[(sulfonylimino)methyl]cyclopentane in good yields. Three is a magic number: On treatment of triazoles with [Rh2(C7H15CO2)4], the rhodium catalyst plays three roles, denitrogenation, C-H bond activation, and stereoselective cyclization, providing a new method for heterocycle synthesis. Intramolecular C-H bond insertion takes place at the benzylic position to give pyrrolidines and related heterocycles in good yields.

Amine oxidative N-dealkylation via cupric hydroperoxide Cu-OOH homolytic cleavage followed by site-specific fenton chemistry

Copper(II) hydroperoxide species are significant intermediates in processes such as fuel cells and (bio)chemical oxidations, all involving stepwise reduction of molecular oxygen. We previously reported a CuII-OOH species that performs oxidative N-dealkylation on a dibenzylamino group that is appended to the 6-position of a pyridyl donor of a tripodal tetradentate ligand. To obtain insights into the mechanism of this process, reaction kinetics and products were determined employing ligand substrates with various para-substituent dibenzyl pairs (-H,-H; -H,-Cl; -H,-OMe, and -Cl,-OMe), or with partially or fully deuterated dibenzyl N-(CH2Ph)2 moieties. A series of ligand-copper(II) bis-perchlorate complexes were synthesized, characterized, and the X-ray structures of the -H,-OMe analogue were determined. The corresponding metastable CuII-OOH species were generated by addition of H2O2/base in acetone at -90 °C. These convert (t1/2 ≈ 53 s) to oxidatively N-dealkylated products, producing para-substituted benzaldehydes. Based on the experimental observations and supporting DFT calculations, a reaction mechanism involving dibenzylamine H-atom abstraction or electron-transfer oxidation by the CuII-OOH entity could be ruled out. It is concluded that the chemistry proceeds by rate limiting Cu-O homolytic cleavage of the CuII-(OOH) species, followed by site-specific copper Fenton chemistry. As a process of broad interest in copper as well as iron oxidative (bio)chemistries, a detailed computational analysis was performed, indicating that a CuIOOH species undergoes O-O homolytic cleavage to yield a hydroxyl radical and CuIIOH rather than heterolytic cleavage to yield water and a CuII-O?- species.

Catalytic Amine Oxidation under Ambient Aerobic Conditions: Mimicry of Monoamine Oxidase B

The flavoenzyme monoamine oxidase (MAO) regulates mammalian behavioral patterns by modulating neurotransmitters such as adrenaline and serotonin. The mechanistic basis which underpins this enzyme is far from agreed upon. Reported herein is that the combination of a synthetic flavin and alloxan generates a catalyst system which facilitates biomimetic amine oxidation. Mechanistic and electron paramagnetic (EPR) spectroscopic data supports the conclusion that the reaction proceeds through a radical manifold. This data provides the first example of a biorelevant synthetic model for monoamine oxidase B activity.

Predictably selective (sp3)C-O bond formation through copper catalyzed dehydrogenative coupling: Facile synthesis of dihydro-oxazinone derivatives

An intramolecular dehydrogenative (sp3)C-O bond formation in salicylamides can be initiated by an active Cu/O2 species to generate pharamaceutically relevant dihydro-oxazinones. Experimental findings suggest that stereoelectronic parameters in both coupling partners are controlling factors for site selectivity in bond formation. Mechanistic investigations including isotope labeling, kinetic studies helped to propose a catalytic cycle. The method provides a convenient synthesis of an investigational new medicine CX-614, which has potential in finding treatment for Parkinson's and Alzheimer's diseases.

Selective formation of imines by aerobic photocatalytic oxidation of amines on TiO2

An oxygenation pathway: The title transformation involves a two-step process: a selective oxygenation step to generate aldehyde intermediates and a subsequent condensation step to afford the imine products (see scheme).

Nitrogen kinetic isotope effects for the monoamine oxidase B-catalyzed oxidation of benzylamine and (1,1-2H2)benzylamine: Nitrogen rehybridization and CH bond cleavage are not concerted

Nitrogen kinetic isotope effects for the oxidation of benzylamine and (1,1-2H2)benzylamine by recombinant human monoamine oxidase B show that cleavage of the CH bond is not concerted with rehybridization of the nitrogen atom.

Complete replacement of H2 by D2 via Pd/C-catalyzed H/D exchange reaction

(Chemical Equation Presented) A general and in situ D2 gas generation method using 10% Pd/C-catalyzed H2-D2 exchange reaction in a H2-D2O system has been developed. H 2 gas sealed in a reac

Oxidative N-debenzylation of N-benzyl-N-substituted benzylamines catalyzed by horseradish peroxidase

A report on the oxidative N-debenzylation of N-benyl-N-substituted benzylamines catalyzed by horseradish peroxidase was presented. A solution of benzylamine in benzene was added to a benzene solution of p-anisaldehyde in 100 ml flask over 10 minutes. Expulsion of proton and hydroxylation yielding α-hydroxylamines were followed by the formation of benzaldehydes and benzylamines.