135-61-5

Basic information

• Product Name: Naphthol AS-D
• Synonyms: 1-(2',3'-Hydroxynaphthoylamino)-2-methylbenzene;2-Naphtho-o-toluidide, 3-hydroxy-;3-hydroxy-n-(2-methylphenyl)-2-naphthalenecarboxamid;Acco Naf-Sol AS-D;Acco Naphthol AS-D;Acna Naphthol E;AcnaNaphtholE;Amanil Naphthol AS-D
• CAS NO: 135-61-5
• Molecular Formula: C₁₈H₁₅NO₂
• Molecular Weight: 277.32
• EINECS: 205-205-0
• Product Categories: Intermediates of Dyes and Pigments;Substrates
• Mol File: 135-61-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 196-198 °C
• Boiling Point: 399.689 °C at 760 mmHg
• Flash Point: 195.525 °C
• Appearance: off-white powder
• Density: 1.277 g/cm³
• Vapor Pressure: 5.83E-07mmHg at 25°C
• Refractive Index: 1.715
• PKA: 8.73±0.40(Predicted)
• CAS DataBase Reference: Naphthol AS-D(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthol AS-D(135-61-5)
• EPA Substance Registry System: Naphthol AS-D(135-61-5)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 135-61-5(Hazardous Substances Data)

Usage

Uses

Used in Textile Industry:
Naphthol AS-D is used as a dyeing agent for cotton yarns, cotton fabric, PVA, viscose, silk, and acetate fibers. It is utilized for direct printing, cotton print, and dye discharge printing. It also serves as a quick pigment and an intermediate for organic pigments. Naphthol AS-D has low affinity for cotton and medium coupling ability.

Preparation

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

Flammability and Explosibility

Nonflammable

Purification Methods

Purify it by recrystallisation from xylene. This gives yellow-green fluorescent solutions at pH 8.2-9.5. [IR: Schnopper et al. Anal Chem 31 1542 1959.] The naphthol AS-D acetate is obtained with AcCl, m 168-169o, and with chloroacetyl chloride naphthol AS-D-chloroacetate is obtained [Moloney et al. J Histochem Cytochem 8 200 1960, Burstone Arch Pathology 63 164 1957]. [Beilstein 12 H 505.]

InChI:InChI=1/C18H15NO2/c1-12-6-2-5-9-16(12)19-18(21)15-10-13-7-3-4-8-14(13)11-17(15)20/h2-11,20H,1H3,(H,19,21)

Upstream product

• 883-99-8 3-hydroxy-2-naphthoic acid methyl ester 
• 139-13-9 nitrilotriacetic acid 
• 95-53-4 o-toluidine 
• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 614-69-7 2-tolyl isothiocyanate 

Downstream Products

• 27580-13-8 3-(phosphonooxy)-N-(o-tolyl)naphthalene-2-carboxamide 
• 1098782-56-9 dimethyl 2-[2-hydroxy-3-(2-methylphenylcarbamoyl)naphthalen-1-yl]-but-2-enedioate 
• 1098782-64-9 dimethyl 2-(methoxycarbonylmethyl)-4-oxo-3-o-tolyl-3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazine-2-carboxylate 
• 1098782-58-1 diethyl 2-[2-hydroxy-3-(2-methylphenylcarbamoyl)naphthalen-1-yl]-but-2-enedioate 
• 1098782-66-1 diethyl 2-(ethoxycarbonylmethyl)-4-oxo-3-o-tolyl-3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazine-2-carboxylate 
• 1357266-49-9 dimethyl 3-t-butylamino-5-o-tolylcarbamoyl-1H-benzo[f]chromene-1,2-dicarboxylate 
• 1357266-51-3 diethyl 3-cyclohexylamino-5-o-tolylcarbamoyl-1H-benzo[f]chromene-1,2-dicarboxylate 
• 60478-08-2 3-o-tolyl-naphtho[2,3-e][1,3]oxazine-2,4-dione 
• 56400-83-0 3-(o-tolyl)naphtho[2,3-e][1,2,3]oxathiazin-4(3H)-one 2,2-dioxide 

Relevant articles and documents

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.

Synthesis of Polysubstituted 2-Naphthols by Palladium-Catalyzed Intramolecular Arylation/Aromatization Cascade

A palladium-catalyzed intramolecular α-arylation and defluorinative aromatization strategy for the synthesis of polysubstituted 2-naphthols is reported. With ortho-bromobenzyl-substituted α-fluoroketones as the substrates and palladium acetate/triphenylphosphine as the catalyst, this method features good functional group tolerance, readily available catalyst and starting materials, and high yields. The applications of the strategy are demonstrated by the synthesis of useful building blocks, such as naphtha[2,3-b]furan, naphthol AS-D, and ligands/catalysts. (Figure presented.).

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.].

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.

Process for the preparation of pure, aromatic o-hydroxy-carboxylic acid aryl amides

Process for the preparation of pure aromatic o-hydroxy-carboxylic acid aryl amides by condensing an aromatic o-hydroxy-carboxylic acid with an aryl amine in the presence of phosphorus chlorides in an organic solvent or diluent, which process comprises treating the reaction mixture or the reaction product with 1 to 25 %, calculated on the weight of the reaction product, of an aliphatic amino-polycarboxylic acid as chelate forming agent. It is not necessary to purify the products, because they are obtained in such a pure form that they can be used directly as coupling components for azo pigments.