4397-68-6

Upstream product

• 15185-02-1 1,1-dideuteriobenzylamine 
• 151466-80-7 (benzyl-α-d1)phthalimide 
• 932-90-1 Benzaldoxime 
• 100-47-0 benzonitrile 
• 100-46-9 benzylamine 
• 100-52-7 benzaldehyde 
• 3481-15-0 benzyl alcohol-d1 
• 66343-88-2 racemic benzyl-α-d₁ bromide 

Downstream Products

• 151466-81-8 C₁₄H₁₁⁽²⁾H₂N 

Relevant academic research and scientific papers

ON THE MECHANISM OF THE CLAY CATALYZED REACTION OF BENZYLAMINE

The mechanism of the aluminum exchanged Montmorillonite catalyzed reaction of benzylamine was studied with deuterium labelled benzylamine.From the analysis of the product dibenzylamine and the recovered benzylamine extensive hydrogen exchange is observed.An SN2 process is thus unlikely and a process involving an imine is suggested.

Stereochemistry of β-deuterium isotope effects on amine basicity

Secondary β-deuterium isotope effects on amine basicities are measured using a remarkably precise NMR titration method. Deuteration is found to increase the basicity of methylamine, dimethylamine, benzylamine, N,N-dimethylaniline, 2-methyl-2-azanorbornane, and pyrrolizidine. The increase in dimethylamine arises entirely from enthalpy, contrary to a previous report. The method permits a determination of intramolecular isotope effects in 1-benzyl-4-methylpiperidine and 2-benzyl-2-azanorbornane. It is found that deuteration has a larger isotope effect when either antiperiplanar or synperiplanar to a lone pair, but the synperiplanar effect is smaller, as confirmed by computations. The isotope effect is attributed to a lowered zero-point energy of a C-H bond adjacent to an amine nitrogen, arising from delocalization of either a syn or an anti lone pair, and with no detectable angle-independent inductive effect.

β-deuterium Isotope Effects on Amine Basicity, Inductive and Stereochemical

Secondary β deuterium isotope effects on acidity constants of ammonium ions are measured using a remarkably precise NMR titration method. Deuteration is found to increase the basicity of methylamine, dimethylamine, benzylamine, and N,N-dimethylaniline. The effect is attributed to a lowered zero-point energy of a CH bond adjacent to an amine nitrogen. The method permits a determination of the stereochemical dependence of the isotope effect in a locked piperidine, and it is found that deuteration is more effective when antiperiplanar to a lone pair. The values are consistent with a cos2 dependence on dihedral angle, with no detectable angle-independent inductive effect. Copyright

Mechanistic analysis of the 3-methyllumiflavin-promoted oxidative deamination of benzylamine. A potential model for monoamine oxidase catalysis

An investigation designed to probe flavin-promoted oxidative deaminations of amines is described. 3-Methyllumiflavin (3MLF) has been found to promote clean conversion of benzylamine to N-benzylbenzaldimine under acid (HCl or MgCl2) catalyzed, t

Carbon Dioxide. A Reagent for the Protection of Nucleophilic Centers and the Simultaneous Activation for Electrophilic Attack. Part 4. The α-Substitution of (i) Benzyl Alcohol and (ii) Benzylamine

Benzyl alcohol is converted into a variety of α-substituted derivatives by a one-pot sequence involving lithiation of an intermediate hemicarbonate ester.Benzylamine is similarly converted by a one-pot sequence to α-substituted benzylamines: here an intermediate carbamate salt is involved.