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

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

Uses

Used in Pharmaceutical Industry:
Methyl 3-hydroxy-2-naphthoate is used as a key intermediate in the synthesis of pharmaceutical compounds. Its enantiomerically pure form is particularly valuable for the development of chiral drugs, which can have different biological activities and effects based on their stereochemistry.
Used in Chemical Synthesis:
In the field of chemical synthesis, Methyl 3-hydroxy-2-naphthoate serves as a versatile building block for the creation of various organic molecules. Its unique structure and functional groups make it suitable for use in the synthesis of a wide range of compounds, including natural products, agrochemicals, and other specialty chemicals.
Used in Chiral Catalysts:
Methyl 3-hydroxy-2-naphthoate can also be utilized in the development of chiral catalysts. These catalysts are essential in asymmetric synthesis, a technique used to produce enantiomerically pure compounds. The use of chiral catalysts can improve the efficiency and selectivity of chemical reactions, leading to more sustainable and cost-effective processes.
Used in Research and Development:
Due to its unique properties and potential applications, Methyl 3-hydroxy-2-naphthoate is also used in research and development settings. Scientists and researchers can explore its potential uses in various fields, such as materials science, nanotechnology, and environmental chemistry, to discover new applications and improve existing processes.

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

• 67-56-1 methanol 
• 1734-00-5 3-hydroxy-2-naphthoyl chloride 
• 883-62-5 3-methoxy-2-naphthoic acid 
• 92-70-6 3-Hydroxy-2-naphthoic acid 
• 5464-07-3 3-acetoxy-2-naphthoic acid 
• 86163-66-8 naphtho<2,3-b>oxet-2-one 
• 425376-47-2 3-(2-methoxycarbonylmethyl-phenyl)-propynoic acid methyl ester 
• 77-78-1 dimethyl sulfate 
• 34253-08-2 methyl 3-methoxymethoxy-2-naphthoate 
• 74-88-4 methyl iodide 
• 288402-18-6 methyl 3-(trifluoromethanesulfonyloxy)naphthalene-2-carboxylate 
• 10576-12-2 ethyl acetohydroximate 
• 75-91-2 tert.-butylhydroperoxide 
• 64-17-5 ethanol 

Downstream Products

• 55426-75-0 3-(hydroxydiphenylmethyl)naphthalen-2-ol 
• 52888-73-0 methyl 3-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carboxylate 
• 22974-74-9 3-hydroxynaphthalene-2-carboxylic acid hydroxyamide 
• 5394-81-0 methyl 3-hydroxy-4-nitro-2-naphthoate 
• 51420-59-8 4-formyl-3-hydroxynaphthoic acid methyl ester 
• 38399-46-1 2-hydroxy-3-carboxy-1-naphtaldehyde 
• 861073-40-7 4-(α-chloro-4-methyl-benzyl)-3-hydroxy-[2]naphthoic acid methyl ester 
• 859947-54-9 4-(α-bromo-4-methyl-benzyl)-3-hydroxy-[2]naphthoic acid methyl ester 
• 859941-81-4 4-(α-chloro-4-formyl-benzyl)-3-hydroxy-[2]naphthoic acid methyl ester 
• 861073-54-3 4-(α-bromo-4-formyl-benzyl)-3-hydroxy-[2]naphthoic acid methyl ester 
• 871901-35-8 4-(α-chloro-4-nitro-benzyl)-3-hydroxy-[2]naphthoic acid methyl ester 
• 110492-39-2 2-cyclohexyl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine-5-carboxylic acid methyl ester 
• 858022-50-1 4-(α-chloro-benzyl)-3-hydroxy-[2]naphthoic acid methyl ester 
• 861073-52-1 4-(α-bromo-4-methoxy-benzyl)-3-hydroxy-[2]naphthoic acid methyl ester 

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.

Nucleophilic Partners in the Tandem Conjugate Addition-Dieckmann Condensation Reaction: 1. Synthesis of 1,2,3-Trisubstituted Naphthalenes

The scope and limitations of the tandem conjugate addition-Dieckmann condensation for the construction of 1,2,3-trisubstituted naphthalenes is defined. Viable nucleophilic partners in this methodology include organocuprates, active methylenes, and a variety of heteroatom initiators.

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.

Oxorhenium(V) complexes with naphtholate-oxazoline ligands in the catalytic epoxidation of olefins

Four oxorhenium(V) complexes 3a-d equipped with naphtholate-oxazoline based ligands 2a-d have been prepared and characterized by NMR, IR and mass spectroscopy as well as elemental analysis. Ligands 2a-d were prepared in a two-step procedure from commercially available starting materials. Ligands 2a-b and 2c-d are regioisomers to each other regarding the position of the -OH group and oxazoline moiety on the naphthol ring. Reaction of 2a-d with (NBu 4)[ReOCl4] in methanol under reflux gave oxorhenium(V) complexes 3a-d of the type [ReOCl(L)2] as green solids in acceptable to good yields. The molecular structures of complexes 3b and 3d have been determined via single crystal X-ray diffraction analysis and both display a distorted octahedral geometry. Complexes 3a-d are active catalysts for the epoxidation of cyclooctene with tert-butylhydroperoxide (TBHP) showing moderate conversions between 41% and 65%.

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.

The influence of intramolecular hydrogen bonding on the order parameter and photostability properties of dichroic azo dyes in a nematic liquid crystal host

It has been demonstrated that intramolecular hydrogen bonding in two classes of dichroic azo dyes has a generally detrimental effect on order parameter in a nematic liquid crystal host. Derivatives of 4-(N,N- diethylamino)-4'-nitroazobenzene with hydroxy groups intramolecularly hydrogen bonded to the azo group show lower order parameters in E7 nematic liquid crystal than the parent dye, but higher order parameters than corresponding methoxy dyes. 1-Arylazo-2-naphthols with a hydrogen bonding carboxamide group in position 3 exist exclusively in the hydrazone form and show even lower order parameters. Intramolecular hydrogen bonding also has a deleterious effect on photochemical stability.

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.

Synthesis and optical properties of copper(II) and nickel(II) complexes of a highly fluorescent morpholine-derivative

A morpholine substituted methyl 3-hydroxy-2-naphthoate was synthesized. The morpholine derivative displayed an intense fluorescence. Owing to the presence of suitable donor atoms, it was employed for the detection of transition metal ions. The crystals of copper and nickel complexes of the fluorescence active ligand were grown via vapor diffusion method. The ligand structure and its metal complexes were characterized using 1H NMR, IR, HR-MS and single crystal X-ray crystallography. The synthesized ligand displayed selective turn-off fluorescence response in the presence of Cu2+ and Ni2+ ions. Fluorescence active letters were encoded successfully on filter paper utilizing metal complexes as a tool towards digital writing.

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.]

A chromone hydrazide Schiff base fluorescence probe with high selectivity and sensitivity for the detection and discrimination of human serum albumin (HSA) and bovine serum albumin (BSA)

The discrimination and identification of human serum albumin (HSA) and bovine serum albumin (BSA) is very important, which is due to the vital roles of two SAs in biological and pharmaceutical research. Based on structural screening and docking calculation from a series of homologues, a coumarin Schiff base fluorescent probe 3-hydroxy-N′-((4-oxo-4H-chromen-3-yl)methylene)-2-naphthohydrazide (HCNH) has been designed and synthesized, which could effectively discriminate HSA and BSA. The probe HCNH exhibited superior sensitivity toward HSA and BSA with the detection limits of 10.62 nM and 16.03 nM in PBS solution, respectively. The binding mechanism of HCNH with SAs was studied by Job's plot analysis, SA destruction and displacement assay. Molecular docking and DFT methods were utilized to provide deep insight into the spatial conformation change of HCNH and binding sites in HSA/BSA. The conformation of HCNH was significantly influenced by the microenvironment provided by HSA and BSA, therefore its fluorescence emission was affected correspondingly. Non-toxic probe HCNH could be successfully used for fluorescence bio-imaging of HSA in cancer cells, which is significantly different from normal cells and favors the application in medical diagnosis.