883-99-8

Basic information

• Product Name: METHYL 3-HYDROXY-2-NAPHTHOATE
• Synonyms: 2-Naphthalenecarboxylic acid, 3-hydroxy-, methyl ester;3-hydroxy-2-naphthalenecarboxylicacimethylester;beta-Hydroxynaphthoic acid methyl ester;Methyl 3-hydroxy-2-naphthalenecarboxylate;METHYL 2-HYDROXY-3-NAPHTHOATE;METHYL 3-HYDROXY-2-NAPHTHOATE;METHYL BETA-HYDROXYNAPHTHOATE;METHYL B-HYDROXYNAPHTHOATE
• CAS NO: 883-99-8
• Molecular Formula: C₁₂H₁₀O₃
• Molecular Weight: 202.21
• EINECS: 212-936-9
• Product Categories: Color Former & Related Compounds;Functional Materials;Sensitizer;C12 to C63;Carbonyl Compounds;Esters;alcohol|carboxylic ester
• Mol File: 883-99-8.mol
• Article Data: 54

Chemical Properties

• Melting Point: 73-75 °C(lit.)
• Boiling Point: 205-207 °C(lit.)
• Flash Point: 205-207°C/160mm
• Appearance: /
• Density: 1.1868 (rough estimate)
• Vapor Pressure: 8.59E-05mmHg at 25°C
• Refractive Index: 1.5440 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 9.36±0.40(Predicted)
• BRN: 1074526
• CAS DataBase Reference: METHYL 3-HYDROXY-2-NAPHTHOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 3-HYDROXY-2-NAPHTHOATE(883-99-8)
• EPA Substance Registry System: METHYL 3-HYDROXY-2-NAPHTHOATE(883-99-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• F: 9-23
• TSCA: Yes
• Hazardous Substances Data: 883-99-8(Hazardous Substances Data)

Usage

General Description

Methyl 3-hydroxy-2-naphthoate undergoes asymmetric oxidative coupling using mono-N-alkylated octahydrobinaphthyl-2,2′-diamine chiral ligands.

Synthesis

Methyl 3-hydroxy-2-naphthoate is obtained by reacting 3-hydroxy-2-naphthoic acid with methanol in sulphuric acid.3-hydroxy-2-naphthoic acid (1.00 g, 5.31 mmol) was dissolved in methanol (20 ml) and concentrated sulphuric acid (1 ml) and left to reflux overnight with stirring. The reaction mixture was washed with brine (2×10 ml) and extracted with ethyl acetate (3 × 10 ml) upon cooling. The organic extracts were collected, dried with magnesium sulphate and concentrated in vacuo to give the title compound as a yellow powder (976 mg, 91%): mp: 81℃(Lit.: 75 – 76℃);vmax/cm-1 3178 br. m (O-H), 2952 w (aro. C-H), 1515 m (aro. C=C); δH (300 MHz; CDCl3) 10.47 (1H, s, OH), 8.47 (1H, s, C(1)H), 7.79 (1H, d, J 8.3, C(5)H or C(8)H), 7.68 (1H, d, J 8.3, C(5)H or C(8)H), 7.50 (1H, td, J 7.5, 1.1, C(6)H or C(7)H), 7.36-7.29 (2H, m, C(4)H and C(6)H or C(7)H), 4.02 (3H, s, OCH3); δC (75 MHz; CDCl3) 170.3 (Ar- C), 156.3 (Ar-C), 137.9 (Ar-C), 132.5 (Ar-CH), 129.2 (Ar-CH), 129.1 (Ar-CH), 127.1 (Ar-C), 126.3 (Ar-CH), 124.0 (Ar-CH), 114.2 (Ar-C), 111.7 (Ar-CH), 52.6 (OCH3); m/z (-ES) 201 (100%, [M-H]-), 202 (14%, [M]-).

Purification Methods

Crystallise the ester from MeOH (charcoal) containing a little water. [Beilstein 10 IV 1186.]

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

Upstream product

• 55384-90-2 o-Ethinyl-zimtsaeuremethylester 
• 67-56-1 methanol 
• 883-62-5 3-methoxy-2-naphthoic acid 
• 64-17-5 ethanol 
• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 75-91-2 tert.-butylhydroperoxide 
• 288402-18-6 methyl 3-(trifluoromethanesulfonyloxy)naphthalene-2-carboxylate 
• 10576-12-2 ethyl acetohydroximate 
• 74-88-4 methyl iodide 
• 34253-08-2 methyl 3-methoxymethoxy-2-naphthoate 
• 77-78-1 dimethyl sulfate 
• 5464-07-3 3-acetoxy-2-naphthoic acid 
• 1734-00-5 3-hydroxy-2-naphthoyl chloride 
• 425376-47-2 3-(2-methoxycarbonylmethyl-phenyl)-propynoic acid methyl ester 

Downstream Products

• 26889-86-1 3-hydroxy-[2]naphthoic acid-(2-amino-ethylamide) 
• 858022-50-1 4-(α-chloro-benzyl)-3-hydroxy-[2]naphthoic acid methyl ester 
• 447-53-0 1,2-Dihydronaphthalene 
• 92-80-8 2-hydroxy-3-naphthamide 
• 47644-69-9 dimethyl 2,2'-dihydroxy-1,1'-binaphthalene-3,3'-dicarboxylate 
• 82378-95-8 γ--β-naphthol 
• 128702-23-8 (-)-Methyl 2,2'-dihydroxy-1,1'-binaphthalene-3-carboxylate 
• 602-09-5 1,1'-bi-2-naphthol 
• 68376-11-4 methyl 3-phenylnaphthalene-2-carboxylate 
• 2178-02-1 3-phenyl-2-naphthioc acid 
• 128702-23-8 (aS)-methyl 2,2'-dihydroxy-1,1'-binaphthalene-3-carboxylate 
• 1005215-06-4 methyl 3-(2-[2-(2-[3-(methoxycarbonyl)-2-naphthyl]oxyethoxy)ethoxy]ethoxy)-2-naphthoate 
• 194-59-2 7H-dibenzo[c,g]carbazole 

Relevant articles and documents

Aggregation-Induced Emission (AIE) Fluorophore Exhibits a Highly Ratiometric Fluorescent Response to Zn2+ in vitro and in Human Liver Cancer Cells

Two novel organic fluorophores, containing bis-naphthylamide and quinoline motifs, have been designed and synthesized. One of the fluorophores contains an isobutylene unit and exhibits a significant aggregation-induced emission (AIE) and a remarkable highly selective ratiometric fluorescence response towards Zn2+ in solution as well as in human liver cancer cells. The AIE behavior of this fluorophore was fully verified by fluorescence and UV/Vis spectroscopy, quantum yield calculations, and single-crystal X-ray diffraction, which revealed an intricate crystal packing system. Conversely, a fluorophore that lacks the isobutylene moiety did not exhibit any significant fluorescent properties as a result of its more flexible molecular structure that presumably allows free intramolecular rotational processes to occur.

Cyclodimerization and Diels-Alder reaction of a spiroepoxycyclohexadienone with an o-quinodimethane structure

Oxidation of 3-hydroxymethyl-2-naphthol with periodate affords a single exo-syn dimer arising from the intermediate ortho quinonoid spiroepoxycyclohexadienone; the latter can also be trapped by reactive dienophiles.

Synthesis and Clathrates of Oligomeric 2-O-Naphthoide Macrocycles

New macrocyclic O-naphthoides 4-6 were synthesized from dehydration reactions of 3-hydroxy- and 7-tertbutyl- 3-hydroxy-2-naphthoic acids, respectively. Their X-ray structures were determined and their clathrate inclusion properties were investigated. Hexamer 6 formed an inclusion clathrate with four chloroform molecules. The trimer 5, by analogy with tri-o-thymotide, was studied for its potential optical resolution effects.

Two new fluorescent Zn2+ sensors exhibiting different sensing mode with subtle structural changes

Two novel receptors HL-1 and HL-2 without and with hydroxyl groups were designed and synthesised. Both receptors showed highly selective coordination towards Zn2+ and exhibited diverse sensing behaviour due to the structural variations. HL-1 showed monotonous ‘turn-on’ response towards Zn2+ while HL-2 displayed highly Zn2+ sensitive ‘turn on’ and ‘ratiometric’ properties. Detailed Job plot experiment, single crystal data, 1H NMR, ESI-MS, UV–vis and density functional theory calculation studies were conducted to understand the binding modes of HL-1 and HL-2 with Zn2+. These results revealed the binding stoichiometric ratio between receptors and Zn2+ were 1:1 with low detection limits and high binding constants.

Naphthaldehyde-derived ligands: Synthesis and their Ni(II) ion complexation

Three novel diazacrown ether ligands, namely 17-, 18-, and 20-membered O2N2-donor macrocycles derived from 3,3′-[butane-1, 4-diylbis(oxy)]bis(2-naphthalenecarbaldehyde), were prepared and characterized by 1H and 13C NMR spectroscopy and mass spectra. Their host-guest interaction with Ni(II) was studied in DMSO-d 6 using 1H NMR spectroscopy. The stoichiometry of the complex in each case in the concentration range examined was determined to be 1:1 using the continuous variation method (Job's plot). The 17-membered O2N2-donor macrocycle in which the two nitrogen atoms are tethered by three methylene units binds Ni(II) more strongly than the other two macrocycles do. Graphical abstract: [Figure not available: see fulltext.]

Enantioselective Synthesis of 3,3′-Disubstituted 2-Amino-2′-hydroxy-1,1′-binaphthyls by Copper-Catalyzed Aerobic Oxidative Cross-Coupling

A challenging direct asymmetric catalytic aerobic oxidative cross-coupling of 2-naphthylamine and 2-naphthol, using a novel CuI/SPDO system, has been successfully developed for the first time. Enantioenriched 3,3′-disubstituted NOBINs were achieved and could be readily derived to divergent chiral ligands and catalysts. This reaction features high enantioselectivities (up to 96 % ee) and good yields (up to 80 %). The DFT calculations suggest that the F–H interactions between CF3 of L17 and H-1,8 of 2-naphthol, and the π–π stacking between the two coupling partners could play vital roles in the enantiocontrol of this cross-coupling reaction.

Preparation of Acifluorfen-Based Ionic Liquids with Fluorescent Properties for Enhancing Biological Activities and Reducing the Risk to the Aquatic Environment

In this work, 12 novel herbicidal ionic liquids (HILs) based on acifluorfen were prepared by pairing with the fluorescent hydrazides or different alkyl chains for increasing activities and reducing negative impacts on the aquatic environment. The results showed that the fluorescence of coumarin hydrazide in the HILs was applied as the internal and supplementary light source to meet the requirement of light wavelength range of acifluorfen, which improved the phytotoxicity of acifluorfen to weeds by enhancing singlet oxygen generation with increased sunlight utilization. The herbicidal activities of HILs were related positively with the length of chain of cation under high light intensity and depended mainly on the fluorescence characteristic of the cation under low light intensity, and the double salt IL forms of acifluorfen containing coumarin hydrazide and n-hexadecyltrimethylammonium had enhanced efficacies against broadleaf weeds in the field. Compared with acifluorfen sodium, HILs had lower water solubility, better surface activity, weaker mobility in soils, and higher decomposition temperature. These results demonstrated that HILs containing different cations provided a wider scope for fine-tuning of the physicochemical and biological properties of herbicides and established a promising way for the development of environmentally friendly herbicidal formulations.