27438-39-7

Usage

Uses

Used in Organic Chemistry:
1-(MORPHOLINOMETHYL)-2-NAPHTHOL is used as a reagent for the synthesis of various compounds, leveraging its strong nucleophilic properties to facilitate a range of reactions, including the formation of carbon-carbon bonds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(MORPHOLINOMETHYL)-2-NAPHTHOL is used as a key intermediate in the production of various drugs and bioactive molecules, contributing to the development of new therapeutic agents.
Used in Optoelectronics:
1-(MORPHOLINOMETHYL)-2-NAPHTHOL is used as a photoluminescent material in the development of optoelectronic devices, owing to its potential to emit light upon exposure to certain stimuli, which is of interest for applications in display technologies and other electronic components.

InChI:InChI=1/C15H17NO2/c17-15-6-5-12-3-1-2-4-13(12)14(15)11-16-7-9-18-10-8-16/h1-6,17H,7-11H2/p+1

Upstream product

• 110-91-8 morpholine 
• 50-00-0 formaldehyd 
• 135-19-3 β-naphthol 
• 7309-48-0 4-methoxymethyl-morpholine 
• 1096-84-0 bis(2-hydroxy-1-naphthyl)methane 
• 18811-63-7 N-(ethoxymethyl)morpholine 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 
• 7647-01-0 hydrogenchloride 
• 5625-90-1 4-(morpholinomethyl)morpholine 
• 64-17-5 ethanol 
• 5419-02-3 1-dimethylaminomethyl-naphthalen-2-ol 
• 428842-08-4 1,1,1-trifluoro-4-(morpholin-4-yl)but-3-en-2-one 
• 67-56-1 methanol 
• 18516-16-0 2-methyl-2-phenyl-3-hydroxypropanal 

Downstream Products

• 1228664-17-2 O-1-(morpholin-4-ylmethyl)naphthalene-2-yl (4-methoxyphenyl)phosphonodithioate 
• 56771-15-4 1-methyl-5,6,7,8-tetrahydro-2-naphthol 
• 1076-26-2 1-methyl-2-naphthol 

Relevant academic research and scientific papers

Intramolecular Interactions I. The Use of Some Mannich Bases of Naphthols as Model Compounds for Intramolecular Hydrogen Bonding

Some model compounds for intramolecular hydrogen bonding are presented.The nmr, IR, UV and fluorescence spectra are shown to be suited for the study of such hydrogen bonds. - Keywords: Hydrogen bond; Intramolecular proton transfer; Mannich bases

Dioxazaborenines

The reaction of 2-naphthol with hexamethylenetetramine in the presence of boric acid in 2-ethoxyethanol gives the dioxazaborenine 2, which can be hydrolozed to the phenolic Mannich base 1.An analogous derivative 4 is produced from 1 and dihydroxyphenylborane (3), while hydroxydiphenylborane (5) yields a labile boron chelate 7, which on heating undergoes amine elimination to yield 8 and the quinone methide 11.

Synthesis of phenols and naphthol with n-morpholinomethyl pendants and their dimethylgallium complexes: Crystal structure of dimethylgallium-[4-nitro-2-(n-morpholinomethyl)-1-phenoxide]

The one-pot Mannich reaction was used to synthesize 2-(n-morpholinomethyl)-1-phenol (1a), 4-methyl-2-(n-morpholinomethyl)-1-phenol (1b), 4-chloro-2-(n-morpholinomethyl)-1-phenol (1c), 4-nitro-2-(n-morpholinomethyl)-1-phenol (1d), and 1-(n-morpholinomethyl)-naphthol (1e). The dimethylgallium complexes of these compounds have been prepared, and compound 2d has been determined by X-ray crystallography. The complex 2d crystallized with one unit having two identical molecules which have intermolecular contacts between the two phenyls caused by face to face π-π stacking. The Ga-O bond distances are noticeably shorter than in the other dimethylgallium phenoxides reported.

Acetyl Acetone Covalent Triazine Framework: An Efficient Carbon Capture and Storage Material and a Highly Stable Heterogeneous Catalyst

We present, for the first time, Covalent Triazine Frameworks functionalized with acetyl acetonate group (acac-CTFs). They are obtained from the polymerization of 4,4'-malonyldibenzonitrile under ionothermal conditions and exhibit BET surface areas up to 1626 m2/g. The materials show excellent CO2 uptake (3.30 mmol/g at 273 K and 1 bar), H2 storage capacity (1.53 wt% at 77 K and 1 bar) and a good CO2/N2 selectivity (up to 46 at 298 K). The enhanced CO2 uptake value and good selectivity are due to the presence of dual polar sites (N and O) throughout the material. In addition, acac-CTF was used to anchor VO(acac)2 as a heterogeneous catalyst. The V@acacCTF showed outstanding reactivity and reusability for the modified Mannich-type reaction with a higher turnover number than the homogeneous catalyst. The higher reactivity and reusability of the catalyst comes from the coordination of the vanadyl ions to the acetyl acetonate groups present in the material. The strong metalation is confirmed from Fourier Transform Infrared analysis, 13C MAS NMR spectral analysis and X-ray photoelectron spectroscopy measurement. Detailed characterization of the V@acac-CTF reveals that electron donation from O^O of the acetyl acetonate group to VO(acac)2, combined with the very high surface area of acac-CTF, is responsible for the stabilization of the catalyst. Overall, this contribution highlights the necessity of stable catalytic binding sites on heterogeneous supports to fabricate greener catalysts for sustainable chemistry.

An efficient and green method for the synthesis of Betti base employing nano-SiO2–H3BO3 as a novel recyclable heterogeneous catalyst

Abstract: In this research, nano-SiO2–H3BO3 is introduced as a novel environmentally benign and recyclable heterogeneous catalyst for the synthesis of aminonaphthols under solvent-free conditions without an additional co-catalyst or additive in air. This synthesis method offers several advantages, such as a green and eco-friendly protocol, operational simplicity, mild reaction conditions, short reaction times, higher yields and easy work-up procedures. The work-up of these very clean reactions involves only recrystallization of the product from ethanol and recovery of the catalyst by filtration. The catalyst can be reused several times without losing activity.

Cu(II)-Catalyzed ortho-Selective Aminomethylation of Phenols

A Cu(II)-catalyzed ortho-selective functionalization of free phenols with trifluoroborates to afford Csp2-Csp3 coupling products under mild conditions has been developed. A variety of functional groups on the phenol and the potassium aminomethyltrifluoroborate substrates were found compatible, furnishing the corresponding products in moderate to excellent yields. A single-electron transfer radical coupling mechanism involving a six-membered transition state is proposed to rationalize the high levels of ortho-selectivity in the reaction. This protocol provides straightforward access to ortho-aminomethyl-substituted phenols, unnatural amino acids and other bioactive small molecules.

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.

Reaction of Push-Pull Enaminoketones and in Situ Generated ortho-Quinone Methides: Synthesis of 3-Acyl-4H-chromenes and 2-Acyl-1H-benzo[f]chromenes as Precursors for Hydroxybenzylated Heterocycles

A simple and efficient method for the synthesis of 4H-chromenes and 1H-benzo[f]chromenes containing a trifluoroacetyl or aroyl group in the pyran ring from o-quinone methide precursors and push-pull enaminoketones has been developed. The chromenes are presumably formed through an initial oxa-Diels-Alder reaction, followed by an elimination of amine. The possibility of further transformations of given chromenes to o-hydroxybenzylated pyrazoles, isoxazoles, and pyridines has been demonstrated.

Magnesium sulfate promoted efficient and green synthesis of aminoalkyl, amidoalkyl and diarylmethane derivatives

Under solvent-free condition, magnesium sulfate promoted the synthesis of substituted aminoalkyl naphthols, amidoalkyl naphthols and diarylmethane derivatives in excellent yield. Robust dehydrating nature and mild Lewis acidity of magnesium sulfate was exploited to carry out all the transformations.

β-naphthol in glycerol: A versatile pair for efficient and convenient synthesis of aminonaphthols, naphtho-1,3-oxazines, and benzoxanthenes

Three-component Betti reaction was carried out in the environmentally benign, inexpensive, non-toxic solvent glycerol. Even in the absence of a catalyst, the reaction went completion with an unprecedented high rate and the expected Betti bases were obtained in up to 91% yield. The reaction works well for representative cyclic, acyclic, aliphatic, and aromatic amines and aldehydes. A benzoxanthene was also prepared in 93% yield following the same methodology with 20 mol% methanesulfonic acid catalyst. Georg Thieme Verlag Stuttgart New York.