92-77-3

Basic information

• Product Name: Naphthol AS
• Synonyms: NAPTHOL AS;NAPHTHOL AS(TM);NAPHTHOL AS;TEREPHTHALBIS(O-HYDROXYANILIDE);AZOIC COUPLING COMPONENT 2;azoic coupling component 4;CI 37505;c.i. 37560
• CAS NO: 92-77-3
• Molecular Formula: C₁₇H₁₃NO₂
• Molecular Weight: 263.29
• EINECS: 202-188-1
• Product Categories: Intermediates of Dyes and Pigments;Organics;Fluorescent;Naphthalene
• Mol File: 92-77-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 246-248 °C(lit.)
• Boiling Point: 406.53°C (rough estimate)
• Flash Point: 190.738 °C
• Appearance: Beige/Powder
• Density: 1.1138 (rough estimate)
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Solubility Insoluble in water; sparingly soluble in ethanol
• PKA: 9.70(at 25℃)
• CAS DataBase Reference: Naphthol AS(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthol AS(92-77-3)
• EPA Substance Registry System: Naphthol AS(92-77-3)

Safety Data

• Hazard Codes: Xi,N
• Statements: 43-51/53
• Safety Statements: 36/37-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 1
• RTECS: QJ1897400
• F: 10-21
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 92-77-3(Hazardous Substances Data)

Usage

Description

Naphthol AS, also known as Naphthol AS-G or Naphthol AS-L, is a coupling agent used in the dyeing and printing of cotton fabrics. It is a beige powder with a melting point of 243-244°C and is sensitive to air. Naphthol AS is soluble in hot water and slightly soluble in ethanol, but insoluble in water and sodium carbonate solution.

Uses

Used in Textile Industry:
Naphthol AS is used as a coupling agent for cotton fabric dyeing and printing. It has low affinity for cotton and medium coupling ability, making it suitable for dyeing cotton yarn, polyester/cotton blends, PVA, viscose, silk, and acetate fibers. It can be used for direct printing, reactive dye printing, and cotton fabric dye printing, as well as for discharge printing, reactive dyes color printing, and dyeing.
Used in Pharmaceutical Industry:
Naphthol AS is also used in the production of quick pigments, fast amine elements, and fast sulfonylurea medications.
Occupational dermatitis has been reported in individuals involved in needlework, likely due to sensitization from occupational contact with clothes dyed or printed using Naphthol AS.

Preparation

aniline and 3-Hydroxy-2-naphthoic acid?condensation.

Contact allergens

Naphthol AS is a coupling agent in cotton dyeing, inducing occupational dermatitis or contact allergy in consumers in contact with cotton-dyed clothing. It has been indirectly reported as a cause of occupational allergy due to its coupling with Diazo Component 51, or as a crosssensitizer or sensitizer associated with Pigment Red 23 in red parts of tattoos. Pigmented contact dermatitis is usual in patients with a high phototype.

Purification Methods

Crystallise it from xylene or AcOH which forms plates m 243-244o [Schnopper et al. Anal Chem 31 1542 1959]. [Beilstein 12 H 505.]

InChI:InChI=1/C17H13NO2/c19-16-11-13-7-5-4-6-12(13)10-15(16)17(20)18-14-8-2-1-3-9-14/h1-11,19H,(H,18,20)

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 103-84-4 Acetanilid 
• 62-53-3 aniline 
• 871874-72-5 2-hydroxy-3-phenylcarbamoyl-naphthalene-1-sulfonic acid 
• 7732-18-5 water 
• 1163-67-3 3-acetoxy-[2]naphthoic acid anilide 
• 102-07-8 bis(diphenyl)urea 
• 18440-21-6 2,4-bis(anilino)-1,3-diphenyl-1,3,2,4-diazadiphosphetidine 
• 1734-00-5 3-hydroxy-2-naphthoyl chloride 
• 443663-72-7 3-(benzoyloxy)-2-naphthoic acid 
• 5464-07-3 3-acetoxy-2-naphthoic acid 

Downstream Products

• 36144-77-1 3,3'-dihydroxy-4,4'-methanediyl-di-[2]naphthoic acid dianilide 
• 3789-75-1 1-phenylazo-2-hydroxy-3-phenylcarbamoylnaphthalene 
• 23421-81-0 4-amino-3-hydroxy-[2]naphthoic acid anilide 
• 6300-52-3 1-(4-nitrophenylazo)-2-hydroxynaphthalene-3-carboxanilide 
• 17809-73-3 3-hydroxy-4-(4-methoxy-phenylazo)-[2]naphthoic acid anilide 
• 14449-94-6 3-hydroxy-4-p-tolylazo-[2]naphthoic acid anilide 
• 52084-73-8 4-formyl-3-hydroxy-[2]naphthoic acid anilide 
• 3844-76-6 4-dimethylaminomethyl-3-hydroxy-[2]naphthoic acid anilide 
• 61858-10-4 2-imino-3-phenyl-2,3-dihydro-naphtho[2,3-e][1,3]oxazin-4-one 
• 56400-80-7 2,2-dioxo-3-phenyl-2,3-dihydro-2λ⁶-naphtho[2,3-e][1,2,3]oxathiazin-4-one 
• 148965-14-4 3-hydroxy-N-phenyl-5,6,7,8-tetrahydronaphthalene-2-carboxamide 
• 17352-47-5 4-(2,5-diethoxy-4-benzoylamino-phenylazo)-3-hydroxy-[2]naphthoic acid anilide 

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.