135-62-6

Basic information

• Product Name: Naphthol AS-OL
• Synonyms: 3-HYDROXY-N-(2-METHOXYPHENYL)-2-NAPHTHALENECARBOXAMIDE;3-HYDROXY-N-(2-METHOXYPHENYL)-2-NAPHTHAMIDE;3-HYDROXY-2-NAPHTHOYL-O-ANISIDIDE;2-HYDROXY-3-NAPHTHOIC ACID O-ANISIDIDE;2-HYDROXY-3-NAPHTHOYL-O-ANISIDIDE;1-(2',3'-Hydroxynaphthoylamino)-2-methoxybenzene;2-(3-Hydroxy-2-naphthamido)anisole;2'-Methoxy-2-hydroxy-3-naphthanilide
• CAS NO: 135-62-6
• Molecular Formula: C₁₈H₁₅NO₃
• Molecular Weight: 293.32
• EINECS: 205-206-6
• Product Categories: Intermediates of Dyes and Pigments;Substrates
• Mol File: 135-62-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 161-164 °C(lit.)
• Boiling Point: 424.1 °C at 760 mmHg
• Flash Point: 210.3 °C
• Appearance: /
• Density: 1.304 g/cm³
• Vapor Pressure: 8.59E-08mmHg at 25°C
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.74±0.40(Predicted)
• CAS DataBase Reference: Naphthol AS-OL(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthol AS-OL(135-62-6)
• EPA Substance Registry System: Naphthol AS-OL(135-62-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 135-62-6(Hazardous Substances Data)

Usage

Description

Naphthol AS-OL is a brown powder with a melting point of 167 to 168 degrees Celsius. It is insoluble in water, slightly soluble in sodium carbonate solution, and soluble in ethanol. When dissolved in sodium hydroxide solution, it turns yellow and is somewhat sensitive to air.

Uses

Used in Textile Industry:
Naphthol AS-OL is used as a dyeing agent for various types of fibers, including cotton yarns, cotton, cotton cloth, towels, bath towels, PVA, viscose, silk, polyamide fiber, and two vinegar fibers, as well as for cotton cloth dyeing in direct printing and discharge printing processes. It is utilized for its ability to provide color and enhance the quality of the final product.
Used in Chemical Industry:
Naphthol AS-OL is also used in the production of quick pigments, fast amine elements, and fast sulfonylurea medications. Its low affinity for cotton and medium coupling ability make it a suitable choice for these applications, contributing to the development of various chemical products and pharmaceuticals.

Preparation

O-Anisidine and 3-Hydroxy-2-naphthoic acid condensation.

InChI:InChI=1/C18H15NO3.Na/c1-22-17-9-5-4-8-15(17)19-18(21)14-10-12-6-2-3-7-13(12)11-16(14)20;/h2-11,20H,1H3,(H,19,21);/q;+1/p-1

Upstream product

• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 1734-00-5 3-hydroxy-2-naphthoyl chloride 
• 90-04-0 2-methoxy-phenylamine 
• 95-55-6 2-amino-phenol 
• 3288-04-8 1-isothiocyanato-2-methoxybenzene 

Downstream Products

• 115228-82-5 3-hydroxy-4-(3-nitro-phenylazo)-[2]naphthoic acid-(5-chloromethyl-2-methoxy-anilide) 
• 105143-77-9 4-(2,5-dichloro-phenylazo)-3-(3-sulfo-benzoyloxy)-[2]naphthoic acid-[N-(3-sulfo-benzoyl)-o-anisidide] 
• 84522-15-6 Phosphoric acid mono-[3-(2-methoxy-phenylcarbamoyl)-naphthalen-2-yl] ester 
• 128580-23-4 2-[(4-{N'-[3-(2-Methoxy-phenylcarbamoyl)-2-oxo-2H-naphthalen-(1Z)-ylidene]-hydrazino}-phenylazo)-(4-nitro-phenyl)-methylene]-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester 
• 128580-24-5 2-[(4-Chloro-phenyl)-(4-{N'-[3-(2-methoxy-phenylcarbamoyl)-2-oxo-2H-naphthalen-(1Z)-ylidene]-hydrazino}-phenylazo)-methylene]-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester 
• 128580-25-6 2-[(4-Bromo-phenyl)-(4-{N'-[3-(2-methoxy-phenylcarbamoyl)-2-oxo-2H-naphthalen-(1Z)-ylidene]-hydrazino}-phenylazo)-methylene]-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester 
• 128556-20-7 4-{[4-({(4-Nitro-phenyl)-[4-(4-nitro-phenyl)-[1,3]dithiol-(2Z)-ylidene]-methyl}-azo)-phenyl]-hydrazono}-3-oxo-3,4-dihydro-naphthalene-2-carboxylic acid (2-methoxy-phenyl)-amide 
• 128556-16-1 4-[(4-{[(4-Chloro-phenyl)-(4,5-diphenyl-[1,3]dithiol-2-ylidene)-methyl]-azo}-phenyl)-hydrazono]-3-oxo-3,4-dihydro-naphthalene-2-carboxylic acid (2-methoxy-phenyl)-amide 

Relevant articles and documents

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.

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.