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

Description

3-Hydroxy-4'-methoxy-2-naphthanilide is a light brown powder that forms frond-like crystals when dissolved in ethanol. It has a melting point of 229-230°C and is insoluble in water and sodium carbonate solutions but soluble in pyridine. In sulfuric acid, it exhibits a shallow brown color, while in sodium hydroxide solution, it appears yellow. 3-Hydroxy-4'-methoxy-2-naphthanilide is sensitive to air and is primarily used in the dyeing and printing of cotton fabrics, as well as in the manufacture of pigment fasts.

Uses

Used in Textile Industry:
3-Hydroxy-4'-methoxy-2-naphthanilide is used as a dyeing and printing agent for cotton fabrics, PVA, viscose, silk, and acetate fibers. It provides medium affinity and coupling ability with cotton, making it suitable for various textile applications.
Used in Pigment Manufacturing:
3-Hydroxy-4'-methoxy-2-naphthanilide is also utilized in the production of pigment fasts, which are essential for creating long-lasting and color-fast pigments for various industries, including paints, coatings, and plastics.

Preparation

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

Upstream product

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

Downstream Products

• 17851-68-2 3-hydroxy-N-(4-methoxyphenyl)-4-[(4-methoxyphenyl)azo]naphthalene-2-carboxamide 
• 75001-00-2 4-(4-Diethylamino-phenylazo)-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 
• 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 
• 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.

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.].

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.