17295-11-3

Basic information

• Product Name: METHYL 6-HYDROXY-2-NAPHTHOATE
• Synonyms: 6-HYDROXY-2-NAPHTHOIC ACID METHYL ESTER;METHYL 6-HYDROXY-2-NAPHTHOATE;2-Naphthalenecarboxylic acid, 6-hydroxy-, Methyl ester;6-hydroxynaphthalene-2-carboxylic acid Methyl ester
• CAS NO: 17295-11-3
• Molecular Formula: C₁₂H₁₀O₃
• Molecular Weight: 202.21
• Mol File: 17295-11-3.mol

Chemical Properties

• Melting Point: 170 °C
• Boiling Point: 368.5°Cat760mmHg
• Flash Point: 163°C
• Appearance: /
• Density: 1.264g/cm³
• Vapor Pressure: 6E-06mmHg at 25°C
• Refractive Index: 1.642
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 8.83±0.40(Predicted)
• CAS DataBase Reference: METHYL 6-HYDROXY-2-NAPHTHOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 6-HYDROXY-2-NAPHTHOATE(17295-11-3)
• EPA Substance Registry System: METHYL 6-HYDROXY-2-NAPHTHOATE(17295-11-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 17295-11-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 6-HYDROXY-2-NAPHTHOATE is used as a chemical intermediate for the synthesis of various pharmaceuticals, particularly for the development of anti-inflammatory, antioxidant, and anti-cancer drugs. Its unique structure allows it to be a key component in the formulation of these medicinal compounds, contributing to their therapeutic effects.
Used in Dye and Pigment Industry:
METHYL 6-HYDROXY-2-NAPHTHOATE is used as a precursor in the production of colorants and pigments. Its chemical properties make it suitable for creating a variety of dyes and pigments used in different applications, such as textiles, plastics, and printing inks.
Used in Organic Compound Synthesis:
METHYL 6-HYDROXY-2-NAPHTHOATE is utilized as a building block in the synthesis of other organic compounds. Its reactivity and functional groups enable it to participate in various chemical reactions, leading to the formation of new compounds with diverse applications across different industries.

InChI:InChI=1/C12H10O3/c1-15-12(14)10-3-2-9-7-11(13)5-4-8(9)6-10/h2-7,13H,1H3

Upstream product

• 67886-70-8 2-cyano-6-methoxynaphthalene 
• 67-56-1 methanol 
• 16712-64-4 6-Hydroxy-2-naphthoic acid 
• 77-76-9 2,2-dimethoxy-propane 
• 7664-93-9 sulfuric acid 
• 101752-05-0 methanol hydrochloride 
• 6343-72-2 6-bromonaphthalen-2-yl acetate 
• 2493-84-7 p-octyloxybenzoic acid 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 616-38-6 carbonic acid dimethyl ester 
• 74-88-4 methyl iodide 
• 3900-45-6 6-methoxy-2-acetylnaphthalene 
• 101513-13-7 methyl 6-isopropyl-2-naphthoate 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 849421-24-5 6-hydroxy-naphthalene-2-carboxylic acid hydrazide 
• 114804-76-1 6-benzyloxynaphthalene-2-carboxylic acid methyl ester 
• 114804-72-7 S(+)-1-Methylheptyl 6-(4-n-octyloxybenzoyloxy)-2-naphthoate 
• 16712-64-4 6-Hydroxy-2-naphthoic acid 
• 1191071-19-8 3,3-bis(4-fluorophenyl)-8-(methoxycarbonyl)-3H-naphtho[2,1-b]pyran 
• 75640-70-9 3,3'-diphenyl-1,1'-bi-2-naphthol 
• 111795-43-8 (R)-3,3’-dibromo-5,5’,6,6’,7,7’,8,8’-octahydro-[1,1’-binaphthalene]-2,2’-diol 
• 287111-93-7 3,3'-diiodo-[1,1'-binaphthalene]-2,2'-diol 
• 1383255-78-4 E-2-carboxy-5-carboxymethylcinnamic acid 
• 1378042-98-8 methyl 6-(diphenylphosphoryl)-2-naphthoate 
• 1160755-51-0 4-[6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-naphthalen-2-ylmethoxy]-benzoic acid 
• 1160755-50-9 4-[6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)naphthalen-2-ylmethoxy]benzoic acid methyl ester 
• 5043-02-7 6-methoxy-2-naphthoic acid methyl ester 

Relevant articles and documents

Synthesis and in vitro biochemical evaluation of a series of alkyl 6-aminosulfonyl naphthanoates as potential inhibitors of human placental estrone sulfatase (ES)

We report the tentative initial results of our on-going search for potent inhibitors of estrone sulfatase (ES), here we report a series of alkyl 6-aminosulfonyl naphthanoate-based compounds as potential inhibitors. The results suggest that the compounds are weak inhibitors in comparison to the standard compound used within the current study.

C -Glycosylation of Substituted β-Naphthols with Trichloroacetimidate Glycosyl Donors

Several glycosyl donors have been systematically investigated for C-glycosylation of substituted β-naphthols to delineate the effect of the substituents. Whereas glycosylations of the parent 2-naphthol are smoothly achievable, those of differently substituted 2-naphthols are cumbersome. Efficiency of the glycosylation depends on the nature of both the glycosyl donors and the substituents of the arene ring. Among various glycosyl donors, trichloroacetimidate glycosyl donors are found to be superior for glycosylation with substituted 2-naphthols.

Symmetrical mesogenic 2,5-bis(6-naphthalen-2-yl)-1,3,4-thiadiazoles

Two series of new symmetrical 1,3,4-oxadiazoles 1a-n and 1,3,4-thiadiazoles 1b-n were prepared and their mesomorphic properties investigated by optical microscopy, differential scanning calorimetry, and powder X-ray diffractometry. Compounds 1b-n are kinetically more stable than compounds 1a-n. Compounds 1a-n exhibited monotropic nematic or smectic C phases, whereas, compounds 1b-n exhibited enantiotropic nematic or smectic A/smectic C phases. Compounds 1b-n have higher clearing temperatures and the larger temperature ranges of mesophases, which might be attributed to the better linearity and/or larger dipole, resulted from a more polarized sulfur atom than oxygen atom incorporated. The fluorescent properties of these two series of 1,3,4-thiadiazole/oxadiazole-based derivatives were also examined. The λmax peaks of the photoluminescence spectra for compounds 1a-6 and 1b-6 measured in THF occurred at ca. 385 nm and 423 nm, respectively. Both series were blue emitters.

Construction, structure diversity, luminescent and dye absorption properties of coordination polymers comprising semi-rigid 6-(carboxymethoxy)-2-naphthoic acid

Semi-rigid 6-(carboxymethoxy)-2-naphthoic acid (H2CNA) was successfully synthesized as a ligand containing O-bridging atom. Six coordination polymers based on H2CNA ligand and transition metal ions were successfully synthesized under the hydrothermal or solvothermal conditions, which named [Zn(CNA)]n (1), [Cd(CNA) (H2O)]n (2), [Co(HCNA)2(H2O)4] (3), [Ni(HCNA)2(H2O)4] (4), [Cu(CNA) (H2O)]n (5), [Ni(CNA) (H2O)]n (6). Single crystal structural analysis revealed that 1, 2, 5 and 6 are shown as 2D structures, and 3–4 displays 0D structures. All the structures assembled into 3D supramolecular networks by hydrogen bonding interaction. The thermal stability, luminescent properties and UV–vis spectra of these coordination polymers were discussed in detail. In addition, 5 has good adsorption ability for Congo Red with good selectivity.

ION CHANNEL ANTAGONISTS/BLOCKERS AND USES THEREOF

Provided are ion channel antagonists/blockers and uses thereof. Specifically, it provides the compounds of formula (I) or pharmaceutically acceptable salts, stereoisomers, solvates or prodrugs, preparation method therefor and application thereof. Definition of each group in the formula can be found in the specification for details. Provided is also pharmaceutical composition useful for treatment of heart disease and other ion channel related diseases.

Novel BQCA- and TBPB-Derived M1 Receptor Hybrid Ligands: Orthosteric Carbachol Differentially Regulates Partial Agonism

Recently, investigations of the complex mechanisms of allostery have led to a deeper understanding of G protein-coupled receptor (GPCR) activation and signaling processes. In this context, muscarinic acetylcholine receptors (mAChRs) are highly relevant due to their exemplary role in the study of allosteric modulation. In this work, we compare and discuss two sets of putatively dualsteric ligands, which were designed to connect carbachol to different types of allosteric ligands. We chose derivatives of TBPB [1-(1′-(2-tolyl)-1,4′-bipiperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one] as M1-selective putative bitopic ligands, and derivatives of benzyl quinolone carboxylic acid (BQCA) as an M1 positive allosteric modulator, varying the distance between the allosteric and orthosteric building blocks. Luciferase protein complementation assays demonstrated that linker length must be carefully chosen to yield either agonist or antagonist behavior. These findings may help to design biased signaling and/or different extents of efficacy.

α-Nitro-α,β-Unsaturated Ketones: An Electrophilic Acyl Transfer Reagent in Catalytic Asymmetric Friedel-Crafts and Michael Reactions

Herein, we introduce α-nitro-α,β-unsaturated ketones as efficient electrophilic acyl transfer reagents, and they were employed in Friedel-Crafts as well as in Michael reactions. The desired acyl transfer products of these reactions were obtained in high yields with high to excellent enantioselectivities with t-leucine-derived squaramide catalyst under mild reaction conditions. Few applications including a synthesis of the isoxazoline motif have been demonstrated.

METHOD FOR PRODUCING 6-HYDROXY-2-NAPHTHOIC ACID ALKYL ESTER

PROBLEM TO BE SOLVED: To provide a method for producing 6-hydroxy-2-naphthoic acid alkyl ester in high yield with and high production efficiency while inhibiting the occurrence of by-products. SOLUTION: A method for producing 6-hydroxy-2-naphthoic acid alkyl ester represented by formula (2) includes the step of, in the presence of an acid catalyst, making the reaction occur between 6-hydroxy-2-naphthoic acid of 1 molar equivalent and an aliphatic alcohol of 1.8-8.0 molar equivalents (where n is an integer of 1-6) SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT

Differentially Substituted Phosphines via Decarbonylation of Acylphosphines

A new route to phosphines was developed by a method that features a "pre-join and transform" process that proceeds via acylphosphine intermediates that may be readily prepared from carboxylic acids and disubstituted phosphines. The efficient decarbonylations of these acylphosphines using a nickel catalyst delivered the corresponding phosphines. This method shows that the carboxyl group can play a role similar to halides or triflates for introducing a substituted phosphorus atom on an aromatic ring.

Assembly and inhibitory activity of monovalent mannosides terminated with aromatic methyl esters: The effect of naphthyl groups

A series of monovalent α-D-mannoside ligands terminated with aromatic methyl esters have been synthesized in excellent yields using the Cu(I) catalyzed azide-alkyne 1,3-dipolar cycloaddition (“click chemistry”). These mannosides were designed to have a unique aglycone moiety (tail) that combines a triazole ring attached to aromatic methyl esters via a six carbon alkyl chain. The mannose unit of these ligands was linked at the ortho, meta, and para positions of substituted methyl benzoates and 1-, 3-, and 6-substituted methyl 2-napthaoates. In hemagglutination assays, ligands (32A-38A) showed better inhibitory activities than the standard inhibitor, methyl α-D-mannopyranoside. Overall, the naphthyl-based mannoside ligand (37A) showed the best activity and therefore merits further development.