6341-75-9

Usage

Chemical class

Naphthalene derivatives

Structure

A naphthalene ring with a hydroxyl group attached to the second carbon atom and a dibenzylamine group attached to the first carbon atom via a methyl bridge

Applications

a. Fluorescent probe in biochemical and biomedical research
b. Potential pharmaceutical applications in drug development for various diseases
c. Organic synthesis and as a building block for creating complex molecules

Unique properties

a. Fluorescence properties useful for research and detection
b. Structural diversity for potential pharmaceutical and synthetic applications

InChI:InChI=1/C25H23NO/c27-25-16-15-22-13-7-8-14-23(22)24(25)19-26(17-20-9-3-1-4-10-20)18-21-11-5-2-6-12-21/h1-16,27H,17-19H2

Upstream product

• 64-17-5 ethanol 
• 58288-30-5 N,N,N′,N′-tetrabenzylmethanediamine 
• 135-19-3 β-naphthol 
• 50-00-0 formaldehyd 
• 103-49-1 dibenzylamine 
• 408507-97-1 1-Methylaminomethyl-[2]naphthol 
• 35141-64-1 2-methyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine 
• 67-56-1 methanol 
• 178425-11-1 N,N-dibenzyl-N-methoxymethylamine 

Relevant academic research and scientific papers

Br?nsted acid catalysed chemo- andortho-selective aminomethylation of phenol

We have developed a Br?nsted acid catalysed highlyortho-selective functionalization of free phenols with readily availableN,O-acetals under mild conditions, furnishing various corresponding aminomethylated phenol products in moderate to excellent yields. The salient features of this transformation include mild conditions, good substrate scope, excellentortho-selectivity, high efficiency, and ease of further transformation.

Manganese-Catalyzed Aminomethylation of Aromatic Compounds with Methanol as a Sustainable C1 Building Block

This study represents the first example of a manganese-catalyzed environmentally benign, practical three-component aminomethylation of activated aromatic compounds including naphtols, phenols, pyridines, indoles, carbazoles, and thiophenes in combination with amines and MeOH as a C1 source. These reactions proceed with high atom efficiency via a sequence of dehydrogenation and condensation steps which give rise to selective C-C and C-N bond formations, thereby releasing hydrogen and water. A well-defined hydride Mn(I) PNP pincer complex, recently developed in our laboratory, catalyzes this process in a very efficient way, and a total of 28 different aminomethylated products were synthesized and isolated yields of up to 91%. In a preliminary study, a related Fe(II) PNP pincer complex was shown to catalyze the methylation of 2-naphtol rather than its aminomethylation displaying again the divergent behavior of isoelectronic Mn(I) and Fe(II) PNP pincer systems.

Efficient catalyst-free four-component synthesis of novel γ-aminoethers mediated by a mannich type reaction

Herein, it is provided an efficient and one-pot procedure for the synthesis of novel and diversely substituted γ-aminoethers in good yields through a four-component process by treatment of benzylamines with polyformaldehyde and activated alkenes in alipha

[Omim][Bf4] ionic liquid, a green and recyclable medium for one-pot aminomethylation of electron-rich aromatic compounds

An efficient catalyst-free procedure has been developed for one-pot aminomethylation of some electron-rich aromatic compounds such as 1- and 2-naphthols, indole, N-methylindol and benzamide, in [omim][BF4] ionic liquid at room temperature. The ionic liquid can be recovered and reused without any noticeable loss of performance.