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

Preparation

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

Properties and Applications

m brown powder, melting point for 167 ~ 168 ℃. Insoluble in water, slightly soluble in sodium carbonate solution, soluble in ethanol. In sodium hydroxide solution for yellow. A little sensitive to the air. This product is mainly used for cotton yarns, cotton, cotton cloth, towel, bath towel, PVA, viscose, silk, polyamide fiber and two vinegar fiber and cotton cloth dyeing of direct printing, the printing and dyeing discharge printing. Can also be used to make quick pigment, fast amine element, element and organic pigment fast sulfonylurea medications. The affinity of cotton low, coupled ability medium.

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

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

Downstream Products

• 122447-74-9 8,13-dioxo-8,13-dihydro-dinaphtho[2,1-b;2',3'-d]furan-6-carboxylic acid o-anisidide 
• 115228-82-5 3-hydroxy-4-(3-nitro-phenylazo)-[2]naphthoic acid-(5-chloromethyl-2-methoxy-anilide) 
• 6410-38-4 1-(2',5'-dichlorophenylazo)-2-hydroxy-3-naphthanilide 
• 61858-11-5 2-imino-3-(2-methoxy-phenyl)-2,3-dihydro-naphtho[2,3-e][1,3]oxazin-4-one 
• 56400-82-9 3-(2-methoxy-phenyl)-2,2-dioxo-2,3-dihydro-2λ⁶-naphtho[2,3-e][1,2,3]oxathiazin-4-one 
• 60499-83-4 3-(2-methoxy-phenyl)-naphtho[2,3-e][1,3]oxazine-2,4-dione 
• 128556-14-9 3-Oxo-4-{[4-({phenyl-[4-phenyl-[1,3]dithiol-(2Z)-ylidene]-methyl}-azo)-phenyl]-hydrazono}-3,4-dihydro-naphthalene-2-carboxylic acid (2-methoxy-phenyl)-amide 
• 128556-13-8 3-Oxo-4-{[4-({phenyl-[4-phenyl-[1,3]diselenol-(2Z)-ylidene]-methyl}-azo)-phenyl]-hydrazono}-3,4-dihydro-naphthalene-2-carboxylic acid (2-methoxy-phenyl)-amide 
• 128556-21-8 3-Oxo-4-{[4-({p-tolyl-[4-p-tolyl-[1,3]dithiol-(2Z)-ylidene]-methyl}-azo)-phenyl]-hydrazono}-3,4-dihydro-naphthalene-2-carboxylic acid (2-methoxy-phenyl)-amide 
• 128556-15-0 4-{[4-({(4-Chloro-phenyl)-[4-phenyl-[1,3]dithiol-(2Z)-ylidene]-methyl}-azo)-phenyl]-hydrazono}-3-oxo-3,4-dihydro-naphthalene-2-carboxylic acid (2-methoxy-phenyl)-amide 
• 128556-22-9 2-[1-(4-Chloro-phenyl)-1-(4-{N'-[3-(2-methoxy-phenylcarbamoyl)-2-oxo-2H-naphthalen-(1Z)-ylidene]-hydrazino}-phenylazo)-meth-(Z)-ylidene]-[1,3]dithiole-4-carboxylic acid methyl ester 
• 128556-17-2 4-{[4-({(4-Fluoro-phenyl)-[4-(4-fluoro-phenyl)-[1,3]dithiol-(2Z)-ylidene]-methyl}-azo)-phenyl]-hydrazono}-3-oxo-3,4-dihydro-naphthalene-2-carboxylic acid (2-methoxy-phenyl)-amide 
• 128556-18-3 4-{[4-({(4-Chloro-phenyl)-[4-(4-chloro-phenyl)-[1,3]dithiol-(2Z)-ylidene]-methyl}-azo)-phenyl]-hydrazono}-3-oxo-3,4-dihydro-naphthalene-2-carboxylic acid (2-methoxy-phenyl)-amide 
• 128556-19-4 4-{[4-({(4-Bromo-phenyl)-[4-(4-bromo-phenyl)-[1,3]dithiol-(2Z)-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-OL by micro-channel continuous method

The invention discloses a method for preparing naphthol AS-OL by a micro-channel continuous method. The method comprises the following specific steps: carrying out an N-acylation reaction in a micro-channel reactor by using 2-hydroxy-3-naphthoic acid and o-toluidine as raw materials to generate N-acyl arylamine naphthol AS-OL, wherein the 2-hydroxy-3-naphthoic acid is a weak acylation reagent andneeds to generate acyl chloride with a dehydrating agent phosphorus trichloride so as to further be subjected to amidation with the o-toluidine. The method comprises: feeding material into a micro-channel reactor through a metering pump, uniformly mixing, carrying out an amidation reaction at 80-150 DEG C for 5-30 minutes, collecting the effluent of the micro-channel reactor, and carrying out steam distillation, water washing, filtering and other steps to obtain the naphthol AS-OL. According to the invention, the yield of the method is 90-96%; and the method is easy to operate and control, short in production period, capable of realizing multiple amplification through parallel connection, free of amplification effect, capable of reducing environmental pollution, few in obtained by-products, high in selectivity, good high product quality and particularly suitable for industrial production.

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.