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

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

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 
• 60499-83-4 3-(2-methoxy-phenyl)-naphtho[2,3-e][1,3]oxazine-2,4-dione 
• 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 

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.

3-Hydroxynaphthalene-2-carboxanilides and their antitrypanosomal activity

Abstract: Series of ring-substituted 3-hydroxynaphthalene-2-carboxanilides were screened for their in vitro activity against wild-type S427 (bloodstream form) of Trypanosoma brucei brucei. 3-Hydroxy-N-(3-trifluoromethylphenyl)- and 3-hydroxy-N-(4-trifluoromethylphenyl)naphthalene-2-carboxamides showed the highest biological activity (MIC?=?1.56 and 2.08?μmol/dm3, respectively). Antitrypanosomal activity was correlated with the experimentally determined lipophilicity and acid–base dissociation constants of the compounds as well as with the calculated electronic properties of individual anilide substituents expressed as Hammett’s σ parameters. The substitution in the meta- or para-position of anilide of derivatives with higher lipophilicity by an electron-withdrawing moiety is favourable for higher activity. The optimum thermodynamic pKa T value was found to be ca. 7.5. The structure–activity relationships of all compounds are discussed. Graphical abstract: [Figure not available: see fulltext.].