92-77-3

Usage

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

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

Downstream Products

• 87700-80-9 3-methoxy-[2]naphthoic acid anilide 
• 24857-91-8 8,13-dioxo-8,13-dihydro-dinaphtho[2,1-b;2',3'-d]furan-6-carboxylic acid anilide 
• 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 
• 85005-63-6 4-(2,4-dinitro-phenylazo)-3-hydroxy-[2]naphthoic acid anilide 
• 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 
• 6300-51-2 3-hydroxy-4-(3-nitro-phenylazo)-[2]naphthoic acid anilide 
• 860246-88-4 trichloro-acetic acid-[N-(2-chloro-2-oxo-2H-2λ⁵-naphth[2,3-e][1,3,2]oxazaphosphinin-4-yl)-anilide] 
• 72845-91-1 4-(9,10-dioxo-9,10-dihydro-[1]anthrylazo)-3-hydroxy-[2]naphthoic acid anilide 
• 79073-28-2 3-hydroxy-4-[1]naphthylazo-[2]naphthoic acid anilide 
• 59970-79-5 4-(4-chloro-2-nitro-phenylazo)-3-hydroxy-[2]naphthoic acid anilide 

Relevant academic research and scientific papers

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.].

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.

Antimycobacterial N-alkoxyphenylhydroxynaphthalenecarboxamides affecting photosystem II

N-(Alkoxyphenyl)-2-hydroxynaphthalene-1-carboxamides (series A) and N-(alkoxyphenyl)-1-hydroxynaphthalene-2-carboxamides (series B) affecting photosystem (PS) II inhibited photosynthetic electron transport (PET) in spinach chloroplasts. Their inhibitory activity depended on the compound lipophilicity as well as on the position of the alkoxy substituent. The most potent PET inhibitors were 2-hydroxy-N-phenylnaphthalene-1-carboxamide and N-[3-(but-2-yloxy)phenyl]-2-hydroxynaphthalene-1-carboxamide within series A (IC50?=?28.9 and 42.5?μM, respectively) and 1-hydroxy-N-(3-propoxyphenyl)naphthalene-2-carboxamide and 1-hydroxy-N-(3-ethoxyphenyl)-naphthalene-2-carboxamide (IC50?=?2.0 and 3.1?μM, respectively) within series B. The inhibitory activity of C′(3) or C′(4) alkoxy substituted compounds of series B was considerably higher than that of C′(2) ones within series A. The PET-inhibiting activities of both series were compared with the PET inhibition of isomeric N-alkoxyphenyl-3-hydroxynaphthalene-2-carboxamides (series C) reported recently. Interactions of the studied compounds with chlorophyll a and aromatic amino acids present in pigment–protein complexes mainly in PS II were documented by fluorescence spectroscopy. The section between P680 and plastoquinone QB in the PET chain occurring on the acceptor side of PS?II can be suggested as the site of action of the compounds.

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.

Antibacterial and herbicidal activity of ring-substituted 3-hydroxynaphthalene-2-carboxanilides

In this study, a series of twenty-two ring-substituted 3-hydroxy- Nphenylnaphthalene- 2-carboxanilides were prepared and characterized. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four Staphylococcus strains and against two mycobacterial species. 3-Hydroxy-N-(2-methoxyphenyl)naphthalene-2-carboxamide showed high biological activity (MIC = 55.0 μmol/L) against S. aureus as well as methicillinresistant strains. N-(2-Fluorophenyl)-3-hydroxynaphthalene-2- carboxamide showed higher activity (MIC = 28.4 μmol/L) against M. marinum than the standard isoniazid and 3-hydroxy-N-(4-nitrophenyl)naphthalene-2- carboxamide expressed higher activity (MIC = 13.0 μmol/L) against M. kansasii than the standard isoniazid. Cytotoxicity assay of effective antimicrobial compounds was performed using the human monocytic leukemia THP-1 cell line. The PET-inhibiting activity expressed by IC50 value of the most active compound 3-hydroxy-N-(3-nitrophenyl)naphthalene-2-carboxamide was 16.9 μmol/L. The structure-activity relationships of all compounds are discussed.

Electrophotographic photoconductor, azo compounds for use in the same, and intermediates for producing the azo compounds

An electrophotographic photoconductor includes an electroconductive support and a photoconductive layer formed thereon which contains a compound having a charge generating moiety and a charge transporting moiety in the molecule thereof. As such a compound for use in the electrophotographic photoconductor, various compounds having a charge generating moiety derived from an azo compound and a charge transporting moiety derived from a triarylamine compound are proposed. Bisazo and trisazo compounds serving as such compounds are also proposed, together with intermediates for producing the bisazo and trisazo compounds.

Naphthalene carboxamides as inhibitors of human cytomegalovirus DNA polymerase

ortho-Hydroxynaphthalene carboxamides have been identified as inhibitors of HCMV DNA polymerase. SAR investigations have demonstrated that both the amide and hydroxy functionalities are required for activity. Substitution on the naphthalene ring has led to inhibitors with submicromolar IC50s against HCMV polymerase. These compounds have been found to be >100-fold selective for inhibition of HCMV polymerase versus human alpha polymerase and display antiviral activity in a cell-based plaque reduction assay. (C) 2000 Elsevier Science Ltd.

CATALYTIC AMINOLYSIS OF 2,3-HYDROXYNAPHTHOIC ACID

The catalytic activity of a series of compounds of group II-VIII elements in the reaction of 2,3-hydroxynaphthoic acid with aniline, leading to 2,3-hydroxynaphthanilide, was investigated.It was shown that the most active catalysts can be arranged in the following order of effectiveness: SbF3 > W(CO)6 > PCl3 > MoO(acac)2 > Zr(SO4)2 Ti(OBu)4 > SbCl5.This does not coincide with the order of effectiveness for the same catalysts in the reaction of benzoic acid with aniline and may be due to the effect of the ortho-located hydroxy group.

Fluorescent substrates for potential use in enzyme-linked immunosorbent assay of membrane-bound nucleic acids

A number of phosphorylated fluorochromes were synthesized and tested for the alkaline phosphatase-linked fluorescence assay of membrane-bound nucleic acids. 3-Hydroxy-N-2′-biphenyl-2-naphthalenecarboxamide phosphate ester (HBNP) was found to be the most suitable for the assay. Nonfluorescent HBNP is hydrolyzed by phospholipase bound to the probe DNA to the highly fluorescent 3-hydroxy-N,2′-biphenyl-2-naphthalenecarboxamide (HBN). HBN is insoluble enough in aqueous medium to precipitate on the nylon membrane. Spots containing as little as 5 fg of λ DNA can be successfully detected on the membrane with HBNP.