481-82-3

Basic information

• Product Name: 1-[AMINO(PHENYL)METHYL]-2-NAPHTHOL HYDROCHLORIDE
• Synonyms: 1-[azanyl(phenyl)methyl]naphthalen-2-ol;1-(aminophenylmethyl)-2-Naphthalenol
• CAS NO: 481-82-3
• Molecular Formula: C₁₇H₁₅NO
• Molecular Weight: 249.31
• Mol File: 481-82-3.mol

Chemical Properties

• Melting Point: 173-175 °C(Solv: ethanol (64-17-5))
• Boiling Point: 451.1°Cat760mmHg
• Flash Point: 226.6°C
• Appearance: /
• Density: 1.211g/cm³
• Vapor Pressure: 9.38E-09mmHg at 25°C
• Refractive Index: 1.691
• PKA: 9.07±0.50(Predicted)
• CAS DataBase Reference: 1-[AMINO(PHENYL)METHYL]-2-NAPHTHOL HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[AMINO(PHENYL)METHYL]-2-NAPHTHOL HYDROCHLORIDE(481-82-3)
• EPA Substance Registry System: 1-[AMINO(PHENYL)METHYL]-2-NAPHTHOL HYDROCHLORIDE(481-82-3)

Safety Data

• Hazardous Substances Data: 481-82-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-[AMINO(PHENYL)METHYL]-2-NAPHTHOL HYDROCHLORIDE is used as an organic synthesis intermediate for the development of new organic compounds. Its unique chemical structure enables it to participate in various chemical reactions, leading to the formation of novel molecules with potential applications in different fields.
Used in Pharmaceutical Industry:
1-[AMINO(PHENYL)METHYL]-2-NAPHTHOL HYDROCHLORIDE is used as a pharmaceutical intermediate in the development of new drugs. Its versatile chemical properties make it an essential component in the synthesis of various pharmaceutical compounds, contributing to the advancement of medical treatments and therapies.
Used in Laboratory Research and Development:
1-[AMINO(PHENYL)METHYL]-2-NAPHTHOL HYDROCHLORIDE is used as a key compound in laboratory research and development processes. Its unique properties and reactivity make it an invaluable tool for scientists and researchers working on the discovery and development of new organic and pharmaceutical compounds.
Used in Chemical Production Process:
1-[AMINO(PHENYL)METHYL]-2-NAPHTHOL HYDROCHLORIDE is used in the chemical production process to synthesize various chemicals and materials. Its role as an intermediate allows for the efficient and cost-effective production of a wide range of products, contributing to the growth and innovation of the chemical industry.

Synthesis

Step 1General/Typical Procedure: General experimental procedures Method A: for compounds 3 (a-i). A mixture of aromatic/heteroaromatic aldehydes (2 mmol), 2-naphthol (1 mmol), and ammonium acetate (1.5 mmol) were taken in a beaker. The reaction mixture was hom ogenized with the help of glass rod and irradiated in microwave oven (360 W) by interval of 10 second. The progress of the reaction was monitored by TLC . After completion, the reaction mixture was cooled to room temperature and was poured over crushed ice. The obtained solid was filtered, dried, and recrystallized from ethanol. 1,3 oxazine derivative 3a, Yield: 98%, Time: 5 minutes. M.P: 147-149°C.Step 2General/Typical Procedure: General experim ental procedures for compounds 4 (a,d-f). Compounds 3(a, d-f) (1 mmol) were taken in 2 ml dil HCl in a beaker and followed by irradiation in a microwave (360 W) for about 5 min. KOH (0.2 mmol) was added and was then irradiated for the appropriate time until the completion of the reaction. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was cooled at room temperature and was poured on crushed ice. The obtained solid was filtered, dried, and recrystallized from ethanol. Aminobenzyl naphthol (Betti base) 4a, Yield: 95%, Time: 15 minutes. M.P: 173-175°C.

InChI:InChI=1/C17H15NO/c18-17(13-7-2-1-3-8-13)16-14-9-5-4-6-12(14)10-11-15(16)19/h1-11,17,19H,18H2

Upstream product

• 7647-01-0 hydrogenchloride 
• 53983-76-9 1-(α-benzylidenamino-benzyl)-[2]naphthol 
• 135-19-3 β-naphthol 
• 100-52-7 benzaldehyde 
• 87-69-4 L-Tartaric acid 
• 50-99-7 D-glucose 
• 1438395-05-1 1-(α-aminobenzyl)-2-naphthol trifluoroacetate 
• 219897-32-2 1-(α-aminobenzyl)-2-naphthol hydrochloride 
• 53983-77-0 1,3-diphenyl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine 
• 561052-90-2 1-(Phenyl-{[1-phenyl-meth-(E)-ylidene]-amino}-methyl)-naphthalen-2-ol 

Downstream Products

• 6278-04-2 1-[phenyl(piperidin-1-yl)methyl]naphthalen-2-ol 
• 97035-67-1 1-(α-piperonylidenamino-benzyl)-[2]naphthol 
• 114000-29-2 1-[α-(3-bromo-benzylidenamino)-benzyl]-[2]naphthol 
• 53983-76-9 1-(α-benzylidenamino-benzyl)-[2]naphthol 
• 1173-40-6 1-(α-cinnamylidenamino-benzyl)-[2]naphthol 
• 96005-21-9 1-[α-(4-dimethylamino-benzylidenamino)-benzyl]-[2]naphthol 
• 113999-72-7 1-[α-(2-bromo-benzylidenamino)-benzyl]-[2]naphthol 
• 24609-75-4 3c-(4-bromo-phenyl)-1r-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine 
• 24609-74-3 3c-(3,4-dichloro-phenyl)-1r-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine 
• 97035-68-2 1-[α-(4-nitro-benzylidenamino)-benzyl]-[2]naphthol 
• 219897-38-8 (S)-(+)-1-(amino(phenyl)methyl)naphthalen-2-ol 
• 100-52-7 benzaldehyde 

Relevant articles and documents

Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones

We have developed a catalytic system based on bianthrylbis(thiourea) for the asymmetric Henry reaction of fluoroketones and nitroalkanes that resulted from the screening of a library containing 31 chiral non-racemic organocatalysts. The corresponding adducts were isolated in up to 6 times shorter reaction time in comparison with the previously published organocatalysts. High levels of stereocontrol have been generally observed, with measured product enantiomeric excesses up to 97% and diastereomeric ratio 3:2 (anti/syn). The above-mentioned catalysts have been successfully applied to the total asymmetric synthesis of CF3-tethered (S)-halostachines, which has proved that this method constitutes an easy entry to similar enantiopure compounds.

Optically pure 1 - (α-aminobenzyl) - 2-naphthol preparation method

The invention provides a preparation method of optical pure 1-(alpha-amino benzyl)-2-naphthol. The preparation method comprises the following steps: catalytically synthesizing racemic 1-(alpha-amino benzyl)-2-naphthol trifluoroacetate by utilizing trifluoroacetic acid; and splitting racemic 1-(alpha-amino benzyl)-2-naphthol and trifluoroacetate thereof by utilizing optical pure 1, 1'-binaphthol phosphate ester and optical pure 1, 1'-binaphthol sodium phosphate as splitting reagents to prepare optical pure 1-(alpha-amino benzyl)-2-naphthol. The method is good in repeatability, and the splitting reagents can be repeatedly used, so that the method is low in cost, environment-friendly and energy-saving, and suitable for large-scale preparation of optical pure 1-(alpha-amino benzyl)-2-naphthol.

Development of chiral heteroleptic magnesium amides; Asymmetric deprotonations mediated by six-membered metallocyclic amidomagnesium naphtholates

A series of enantioenriched six-membered metallocyclic amidomagnesium naphtholates were prepared and used to probe the structure-reactivity/selectivity relationships of heteroleptic magnesium base complexes within asymmetric deprotonation reactions. An ef

A new method for the synthesis of enantiomerically pure Betti base

We have developed a new method for the synthesis of enantiomerically pure Betti base. By using trifluoroacetic acid to replace the more traditionally used hydrochloride acid, the hydrolysis procedure used in the classical synthesis of racemic Betti base was carried out under milder conditions with an improved yield (up to 96%), which was followed by a new and efficient resolution with using recyclable (R)-1,1′-binaphthalene-2,2′-diyl sodium phosphate to provide enantiomerically pure (S)-Betti base in 95% yield with up to 99% ee and (R)-Betti base in 93% yield with 90% ee in one resolution step. Georg Thieme Verlag Stuttgart - New York.

Synthesis, antimicrobial and cytotoxicity study of 1,3-disubstituted-1H- naphtho[1,2-e][1,3]oxazines

A series of new 1,3-disubstituted-1H-naphtho[1,2-e][1,3]oxazines (3 and 7) was synthesized in good yields and the structure was determined with the help of NMR, 2D-NMR, HRMS studies and X-ray crystallography. These compounds were tested in vitro for their

High-performance liquid chromatographic enantioseparation of Betti base analogs on a newly developed isopropyl carbamate-cyclofructan6-based chiral stationary phase

The direct separation of the enantiomers of 1-(α-aminoarylmethyl)-2- naphthol, 1-(α-aminoalkyl)-2-naphthol, 2-(α-aminoarylmethyl)-1- naphthol analogs, and 2-(1-amino-2-methylpropyl)-1-naphthol) was performed on a newly developed chiral stationary phase containing isopropyl carbamate-cyclofructan6 as chiral selector, with n-heptane/alcohol/ trifluoroacetic acid as mobile phase. The effects of the mobile-phase composition, the nature and concentration of the alcoholic and acidic modifiers, and the structures of the analytes on the retention and resolution were investigated. In some cases, separations were carried out at constant mobile-phase compositions in the temperature range 5-40°C. Thermodynamic parameters and Tiso values were calculated from plots of ln k′ or ln α versus 1/T. -Δ(ΔH°) ranged from 2.8 to 3.2 kJ mol-1, -Δ(ΔS°) from 7.7 to 10.1 J mol-1 K-1, and -Δ(ΔG°) from 0.2 to 0.5 kJ mol-1. It was found that the enantioseparations were enthalpy driven. The sequence of elution of the stereoisomers determined in some cases was (R) (S).

One-pot, three-component uncatalyzed quantitative synthesis of new aminonaphthols (Betti bases) in water

One-pot, three-component reaction of 2-naphthol, aromatic aldehyde, and heteroaryl amine in water at room temperature leads to the formation of the corresponding aminonaphthols (Betti bases). Reaction details and study of enantiomeric resolution of 1-(p-m

Substituent effects in the ring-chain tautomerism of 1,3-diaryl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines

Condensation of Betti base analogue amino naphthols with substituted benzaldehydes led to 1,3-diaryl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines (3-9) which proved to be three-component (r1-o-r2) tautomeric mixtures in CDCl3