Methyl 1-hydroxy-2-naphthoate

Base Information

• Chemical Name: Methyl 1-hydroxy-2-naphthoate
• CAS No.: 948-03-8
• Molecular Formula: C12H10 O3
• Molecular Weight: 202.21
• Hs Code.: 2918290000
• European Community (EC) Number: 213-434-2
• DSSTox Substance ID: DTXSID8061341
• Nikkaji Number: J29.231A
• Wikidata: Q63408689
• Mol file: 948-03-8.mol

Synonyms:Methyl 1-hydroxy-2-naphthoate;948-03-8;methyl 1-hydroxynaphthalene-2-carboxylate;2-Naphthalenecarboxylic acid, 1-hydroxy-, methyl ester;1-HYDROXY-2-NAPHTHOIC ACID METHYL ESTER;EINECS 213-434-2;1-Hydroxy-2-naphthoic acid, methyl ester;2-Naphthoic acid, 1-hydroxy-, methyl ester;Methyl1-hydroxy-2-naphthoate;SCHEMBL244541;Methyl=1-hydroxy-2-naphthoate;DTXSID8061341;Methyl 1-naphthol-2-carboxylate;1-Hydroxy-2-carbomethoxynaphthalene;MFCD00043823;STL503159;AKOS001443892;Methyl 1-hydroxy-2-naphthoate, 98%;AS-76264;methyl 1-hydroxy-naphthalene-2-carboxylate;FT-0633181;EN300-28634;D97460;1-hydroxy-naphthalene-2-carboxylic acid methyl ester;Q63408689;Z17871321;F2173-1249

Chemical Property of Methyl 1-hydroxy-2-naphthoate

Chemical Property:

• Vapor Pressure: 8.59E-05mmHg at 25°C
• Melting Point: 76-80 °C(lit.)
• Boiling Point: 330.5°Cat760mmHg
• PKA: 8.09±0.50(Predicted)
• Flash Point: 142.5°C
• PSA: 46.53000
• Density: 1.264g/cm³
• LogP: 2.33200
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 202.062994177
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl 1-hydroxy-2-naphthoate 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1=C(C2=CC=CC=C2C=C1)O
• Uses: Methyl 1-hydroxy-2-naphthoate may be used as a starting reagent for the synthesis of axially chiral benzimidazole derivatives.It may also be employed in the synthesis of the following aza-mollugin derivatives: azamollugin2-desmethyl-azamollugin 2,2-didesmethyl-azamollugin

Technology Process of Methyl 1-hydroxy-2-naphthoate

There total 72 articles about Methyl 1-hydroxy-2-naphthoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

dimethyl sulfate (77-78-1) + 1-hydroxy-2-naphthoic acid (86-48-6) → 1-hydroxy-naphthalene-2-carboxylic acid methyl ester (948-03-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; for 1h; Heating;

DOI:10.1021/jo990035l

Reference yield: 94.0%

methyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate (7442-52-6,125117-36-4) → 1-hydroxy-naphthalene-2-carboxylic acid methyl ester (948-03-8)

Guidance literature:

With copper(l) iodide; caesium carbonate; In 1,4-dioxane; at 70 ℃; for 36h; Reagent/catalyst; Temperature;

DOI:10.1016/j.tet.2016.01.057

Reference yield: 93.0%

methyl 1-hydroxy-3,4-dihydronaphthalene-2-carboxylate (95448-04-7) → 1-hydroxy-naphthalene-2-carboxylic acid methyl ester (948-03-8)

Guidance literature:

With 5-trimethylammonio-1,3-dioxo-1,3-dihydro-1λ⁵-benzo[d][1,2]-iodoxol-1-ol anion; In chloroform; diethylene glycol dimethyl ether; water; at 40 ℃; for 24h;

DOI:10.1021/ol202777h

upstream raw materials:

diazomethane

1-hydroxy-2-naphthoic acid

methanol

1-hydroxy-2-naphthoyl chloride

Downstream raw materials:

(1-Hydroxy-[2]naphthyl)-diphenyl-methanol

methyl 1-methoxy-2-naphthoate

2-(diphenylmethylene)-1(2H)-naphthalenone

1-(4-Chloro-2-nitro-phenoxy)-naphthalene-2-carboxylic acid methyl ester

Refernces

Synthesis of axially chiral oxazoline-carbene ligands with an N-naphthyl framework and a study of their coordination with AuCl·SMe₂

10.3762/bjoc.8.81

The research focuses on the synthesis and coordination behavior of axially chiral oxazoline-carbene ligands with an N-naphthyl framework, specifically their interaction with AuCl·SMe2 to form Au(I) complexes. The main reactants used in the synthesis include methyl 1-hydroxy-2-naphthoate, trifluoromethylation reagents, 2-nitroaniline, Pd/C for reduction, triethyl orthoformate, TsOH for cyclization, and (S)-2-amino-2-phenylethanol, among others. The synthesis process involved several steps, including trifluoromethylation, coupling reactions, reduction, cyclization, and amide formation, leading to the formation of axially chiral ligands. The coordination study with AuCl·SMe2 was conducted using NaOAc in acetonitrile, and the Au(I) complexes were isolated by flash column chromatography. The analysis of the complexes was performed using 1H NMR spectroscopy to compare the chemical shifts of protons on the oxazoline ring before and after complexation, and single-crystal X-ray diffraction studies were employed to confirm the structure of the complexes, revealing a nearly linear coordination geometry around the gold(I) center. The study found that the geometry of the chiral N-naphthyl axis significantly influenced the yields of the Au(I) complexes, with (Sa,S)-7 yielding higher complex yields than (Ra,S)-7.