92-79-5

Basic information

• Product Name: 3-Hydroxy-4'-methoxy-2-naphthanilide
• Synonyms: 2-HYDROXY-3-[(4-METHOXYPHENYL)CARBAMOYL]NAPHTHALENE;2-HYDROXY-3-NAPHTHOYL-P-ANISIDIDE;3-HYDROXY-2-NAPHTHOYL-P-ANISIDIDE;NAPHTHOL AS-RL;NAPTHOL AS-RL;3-hydroxy-4'-methoxy-2-naphthanilide;3-hydroxy-2-naphth-p-anisidide;C.I.Azoic Coupling Component 11
• CAS NO: 92-79-5
• Molecular Formula: C₁₈H₁₅NO₃
• Molecular Weight: 293.32
• EINECS: 202-190-2
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 92-79-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 229~230℃
• Boiling Point: 426.8 °C at 760 mmHg
• Flash Point: 211.9 °C
• Appearance: /
• Density: 1.304 g/cm³
• PKA: 8.75±0.40(Predicted)
• CAS DataBase Reference: 3-Hydroxy-4'-methoxy-2-naphthanilide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-4'-methoxy-2-naphthanilide(92-79-5)
• EPA Substance Registry System: 3-Hydroxy-4'-methoxy-2-naphthanilide(92-79-5)

Safety Data

• Hazardous Substances Data: 92-79-5(Hazardous Substances Data)

Usage

Preparation

p-Anisidine?and 3-Hydroxy-2-naphthoic acid condensation.

Properties and Applications

Light brown powder evenly. In the ethanol frond-like crystal shrinkage, melting point for 229 ~ 230 ℃. Insoluble in water solution and sodium carbonate, soluble in pyridine. In the sulfuric acid is shallow brown in the solution; Sodium hydroxide solution for yellow in the liquid. Sensitive to air. Mainly used for cotton fabrics, PVA, viscose, silk and vinegar fiber dyeing and printing of cotton fabric. Can be used for the manufacture of pigment fast. This product to cotton affinity medium, coupled ability medium.

Upstream product

• 123-30-8 4-amino-phenol 
• 1734-00-5 3-hydroxy-2-naphthoyl chloride 
• 104-94-9 4-methoxy-aniline 
• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 2284-20-0 4-Methoxyphenyl isothiocyanate 

Downstream Products

• 1353641-40-3 C₂₂H₁₆N₆O₃ 
• 1229115-36-9 C₂₆H₁₈N₈O₃ 
• 722541-27-7 4-(1,3-dioxo-1H,3H-benzo[de]isochromen-6-ylazo)-3-hydroxy-naphthalene-2-carboxylic acid (4-methoxy-phenyl)-amide 
• 75000-95-2 3-Hydroxy-4-[4-(4-methoxy-phenylamino)-phenylazo]-naphthalene-2-carboxylic acid (4-methoxy-phenyl)-amide 
• 75001-00-2 4-(4-Diethylamino-phenylazo)-3-hydroxy-naphthalene-2-carboxylic acid (4-methoxy-phenyl)-amide 
• 17851-68-2 3-hydroxy-N-(4-methoxyphenyl)-4-[(4-methoxyphenyl)azo]naphthalene-2-carboxamide 
• 56400-81-8 3-(4-methoxy-phenyl)-2,2-dioxo-2,3-dihydro-2λ⁶-naphtho[2,3-e][1,2,3]oxathiazin-4-one 
• 61858-12-6 2-imino-3-(4-methoxy-phenyl)-2,3-dihydro-naphtho[2,3-e][1,3]oxazin-4-one 
• 16470-35-2 8,13-dioxo-8,13-dihydro-dinaphtho[2,1-b;2',3'-d]furan-6-carboxylic acid p-anisidide 

Relevant articles and documents

Method for preparing naphthol AS series azo dye

The invention belongs to the technical field of chemical engineering, and particularly relates to a method for preparing naphthol AS series azo dye. According to the method, 2-hydroxy-3-naphthoic acid(also called 2,3-acid) and substituted aromatic amine are used as raw materials, and the naphthol AS azo dye is prepared under the catalytic action of a catalyst. In the whole reaction process, the reaction conditions are mild, no hydrogen chloride is generated, and the requirements on equipment are reduced, and therefore, the equipment investment cost is reduced. The by-product of the whole process flow is water, and no waste salt is generated, and therefore, the production process is more environmentally friendly, and the process of new and old kinetic energy conversion in China is promoted. The product purity is high and can reach 99% or above; and the product is light in color, is off-white, off-yellow or slightly red, and is high in quality.

Investigation of hydro-lipophilic properties of n-alkoxyphenylhydroxynaphthalenecarboxamides ?

The evaluation of the lipophilic characteristics of biologically active agents is indispensable for the rational design of ADMET-tailored structure–activity models. N-Alkoxy-3-hydroxynaphthalene-2-carboxanilides, N-alkoxy-1-hydroxynaphthalene-2-carboxanilides, and N-alkoxy-2-hydroxynaphthalene-1-carboxanilides were recently reported as a series of compounds with antimycobacterial, antibacterial, and herbicidal activity. As it was found that the lipophilicity of these biologically active agents determines their activity, the hydro-lipophilic properties of all three series were investigated in this study. All 57 anilides were analyzed using the reversed-phase high-performance liquid chromatography method for the measurement of lipophilicity. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In the present study, a range of software lipophilicity predictors for the estimation of clogP values of a set of N-alkoxyphenylhydroxynaphthalenecarboxamides was employed and subsequently cross-compared with experimental parameters. Thus, the empirical values of lipophilicity (logk) and the distributive parameters (π) were compared with the corresponding in silico characteristics that were calculated using alternative methods for deducing the lipophilic features. To scrutinize (dis)similarities between the derivatives, a PCA procedure was applied to visualize the major differences in the performance of molecules with respect to their lipophilic profile, molecular weight, and violations of Lipinski’s Rule of Five.

Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides

A series of fifteen new N-alkoxyphenylanilides of 3-hydroxynaphthalene-2-carboxylic acid was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra and M. avium subsp. paratuberculosis. Some of the tested compounds showed antibacterial and antimycobacterial activity against the tested strains comparable with or higher than that of the standards ampicillin or rifampicin. 3-Hydroxy-N-(2-propoxyphenyl)naphthalene-2-carboxamide and N-[2-(but-2-yloxy)-phenyl]-3-hydroxynaphthalene-2-carboxamide had MIC = 12 μM against all methicillin-resistant S. aureus strains; thus their activity is 4-fold higher than that of ampicillin. The second mentioned compound as well as 3-hydroxy-N-[3-(prop-2-yloxy)phenyl]-naphthalene-2-carboxamide had MICs = 23 μM and 24 μM against M. tuberculosis respectively. N-[2-(But-2-yloxy)phenyl]-3-hydroxynaphthalene-2-carboxamide demonstrated higher activity against M. avium subsp. paratuberculosis than rifampicin. Screening of the cytotoxicity of the most effective antimycobacterial compounds was performed using THP-1 cells, and no significant lethal effect was observed for the most potent compounds. The compounds were additionally tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. N-(3-Ethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide (IC50 = 4.5 μM) was the most active PET inhibitor. The structure-activity relationships are discussed.