135-65-9

Basic information

• Product Name: 3-Hydroxy-N-(3-nitrophenyl)-2-naphthalenecarboxamide
• Synonyms: DaitoGrounderBS;DiatholBS;KambotholAS-BS;NaphtazolB;NAPHTHOL AS-BS;NAPTHOL AS-BS;2-HYDROXY-3-NAPHTHOIC ACID M-NITROANILIDE;3-HYDROXY-3'-NITRO-2-NAPHTHANILIDE
• CAS NO: 135-65-9
• Molecular Formula: C₁₇H₁₂N₂O₄
• Molecular Weight: 308.29
• EINECS: 205-209-2
• Product Categories: Intermediates of Dyes and Pigments;pigments
• Mol File: 135-65-9.mol

Chemical Properties

• Melting Point: 246-247°C
• Boiling Point: 448 °C at 760 mmHg
• Flash Point: 224.7 °C
• Appearance: /
• Density: 1.449 g/cm³
• Vapor Pressure: 0.001Pa at 20℃
• PKA: 8.65±0.40(Predicted)
• CAS DataBase Reference: 3-Hydroxy-N-(3-nitrophenyl)-2-naphthalenecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-N-(3-nitrophenyl)-2-naphthalenecarboxamide(135-65-9)
• EPA Substance Registry System: 3-Hydroxy-N-(3-nitrophenyl)-2-naphthalenecarboxamide(135-65-9)

Safety Data

• Statements: 36
• Safety Statements: 36-26
• Hazardous Substances Data: 135-65-9(Hazardous Substances Data)

Usage

Uses

Used in Textile Industry:
3-Hydroxy-N-(3-nitrophenyl)-2-naphthalenecarboxamide is used as a dyeing agent for various types of fibers, including cotton yarn, cotton, PVA, viscose, and silk. It is particularly effective for dyeing and discharge printing of cotton fabric, providing high affinity and a medium coupling ability.
Used in Pigment Production:
3-Hydroxy-N-(3-nitrophenyl)-2-naphthalenecarboxamide can also be used to manufacture quick pigments, neutral grains, and organic pigments, which are essential for various industrial applications, including the production of paints, inks, and coatings.

Preparation

M-nitroaniline and 3-Hydroxy-2-naphthoic acid?condensation.

Upstream product

• 1734-00-5 3-hydroxy-2-naphthoyl chloride 
• 99-09-2 3-nitro-aniline 
• 92-70-6 3-Hydroxy-2-naphthoic acid 

Downstream Products

• 16470-56-7 8,13-dioxo-8,13-dihydro-dinaphtho[2,1-b;2',3'-d]furan-6-carboxylic acid-(3-nitro-anilide) 
• 97780-51-3 3,3'-dihydroxy-4,4'-biphenyl-4,4'-diyl-bis-azo-di-[2]naphthoic acid bis-(3-nitro-anilide) 
• 78916-01-5 4-(9,10-dioxo-9,10-dihydro-[2]anthrylazo)-3-hydroxy-[2]naphthoic acid-(3-nitro-anilide) 
• 4880-11-9 3-hydroxy-2-naphthoic acid 3'-aminoanilide 
• 101874-83-3 4-formyl-3-hydroxy-[2]naphthoic acid-(3-nitro-anilide) 
• 60478-02-6 3-(3-nitro-phenyl)-naphtho[2,3-e][1,3]oxazine-2,4-dione 
• 10019-03-1 N-(3-nitrophenyl)-3-(phosphonooxy)naphthalene-2-carboxamide 
• 1174069-51-2 C₂₀H₁₆N₂O₅ 

Relevant articles and documents

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.].

Hydroxy Group Directed Catalytic Hydrosilylation of Amides

Chemo- and site-selective hydrosilylation of α- or β-hydroxy amides using organocatalyst B(C6F5)3 and commercially available hydrosilanes is described. This transformation is operative under mild conditions and tolerates a wide range of functional groups. The reaction was applied for selective reduction of a specific amide group of the therapeutically important cyclic peptide cyclosporin A, demonstrating the potential usefulness of this catalytic method in late-stage structural transformations of drug lead molecules.

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 and β-adrenergic blocking activity of naphthyloxypropylamines

A series of 1-isopropylamino-3-(3′-substituted-2′-naphthyloxy)- 2-propanols have been synthesized and their structures have been confirmed by spectral analysis. All the derivatives have shown β-adrenergic blocking effect when tested on perfused frog heart. Compound 4e exhibited 100% blockade of adrenaline response.

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.

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.