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2-Methoxynaphthalene

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CAS:93-04-9
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2-Methoxynaphthalene Basic information
Product Name:2-Methoxynaphthalene
Synonyms:b-Methoxynaphthalene;Methyl 2-naphtyl ether;2-Methoxynaphthalene, 98% 5GR;6-Methoxy-2-naphthalene;NSC 4171;2-Methoxynaphthalene , 98.0%(GC);-Naphthylmethylether;Nerolin (old)
CAS:93-04-9
MF:C11H10O
MW:158.2
EINECS:202-213-6
Product Categories:Aromatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Food & Feed ADDITIVES;Naphthalene derivatives;93-04-9
Mol File:93-04-9.mol
2-Methoxynaphthalene Structure
2-Methoxynaphthalene Chemical Properties
Melting point 70-73 °C (lit.)
Boiling point 274 °C (lit.)
density 1.064 g/mL at 25 °C (lit.)
vapor pressure 1.097Pa at 25℃
FEMA 4704 | BETA-NAPHTHYL METHYL ETHER
refractive index 1.5440 (estimate)
Fp 272-274°C
storage temp. Sealed in dry,Room Temperature
solubility H2O: soluble (completely)
form Crystalline Solid
pka0[at 20 ℃]
color White to yellow-brown
Odorat 1.00 % in dipropylene glycol. sweet naphthyl floral orange blossom acacia neroli
Odor Typenaphthyl
Water Solubility INSOLUBLE
Merck 14,5997
JECFA Number1257
BRN 1859408
Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKeyLUZDYPLAQQGJEA-UHFFFAOYSA-N
LogP3.318 at 25℃
CAS DataBase Reference93-04-9(CAS DataBase Reference)
NIST Chemistry ReferenceNaphthalene, 2-methoxy-(93-04-9)
EPA Substance Registry SystemNaphthalene, 2-methoxy- (93-04-9)
Safety Information
Safety Statements 22-24/25
RIDADR UN 3077 9 / PGIII
WGK Germany 2
RTECS QJ9468750
TSCA Yes
HS Code 29093090
ToxicityLD50 oral in rat: > 5gm/kg
MSDS Information
ProviderLanguage
Methyl 2-naphthyl ether English
SigmaAldrich English
ACROS English
ALFA English
2-Methoxynaphthalene Usage And Synthesis
Descriptionβ-Naphthyl methyl ether has an intensely sweet, floral odor suggestive of orange blossoms. It is free from naphthol by-odor. It has a sweet, strawberry taste. This may be prepared from potassium β-naphthol and methyl chloride at 300°C; by methylation of β-naphthol with dimethyl sulfate or by direct esterification with methyl alcohol.
Chemical Propertiesβ-Naphthyl methyl ether has an intensely sweet, floral odor suggestive of orange blossoms; free from naphthol by-odor. It has a sweet, strawberry taste
Chemical PropertiesMethyl 2-Naphthyl Ether forms white crystals (mp 73–74°C) with an intense orange blossom odor.
Chemical Propertieswhite powder
Uses2-methoxynaphthalene acylation was used as a model reaction to study the catalytic benefits of delamination. It was also used to study the alkali-metal-mediated manganation (AMMMn) reactions.
Uses2-methoxynaphthalene acylation is used as a model reaction to study the catalytic benefits of delamination. It was also used to study the alkali-metal-mediated manganation (AMMMn) reactions.
Uses2-Methoxynaphthalene is an Impurity of the non-steroidal anti-inflammatory Naproxen (N377525).
PreparationFrom postassium β-naphthol and methyl chloride at 300°C; by methylation of β-naphthlol with dimethyl sulfate or by direct esterification with methyl alcohol
DefinitionChEBI: 2-Methoxynaphthalene is a member of naphthalenes.
Synthesis Reference(s)Tetrahedron, 48, p. 6439, 1992 DOI: 10.1016/S0040-4020(01)88233-8
Tetrahedron Letters, 22, p. 3463, 1981 DOI: 10.1016/S0040-4039(01)81932-8
Flammability and ExplosibilityNot classified
SynthesisPreparation of 2-Methoxynaphthalene from 2-naphthol.
Principle: Phenols can be methylated to give methyl ethers. Methylation can be done either by using diazomethane or dimethyl sulphate in alkaline medium.
Reaction:
Preparation of 2-Methoxynaphthalene from 2-naphthol
Procedure: Take 0.5 g 2-naphthol and 0.2 g NaOH in 5 ml distilled water in a beaker (25 ml). Heat on a wire gauze to obtain a clear solution. Cool the solution (10-15°C) and then add 0.35 ml dimethyl sulphate drop wise. After the addition is over, warm the mixture for one hour at 70-80°C and then cool. Filter the product and wash it with 10% sodium hydroxide solution and then with water. Dry the product, record the practical yield and re-crystallize it.
Re-crystallization: Dissolve the crude product in minimum amount of ethyl alcohol in a beaker by heating on a water bath. Filter the hot solution and cool the filtrate. Filter the white crystals of the product. Dry and record the melting point and TLC (using toluene as solvent).
Purification MethodsFractionally distil the ether under vacuum. Crystallise it from absolute EtOH, aqueous EtOH, *C6H6, pet ether or n-heptane, and dry it under vacuum in an Abderhalden pistol or distil it in vacuo. The picrate has m 118o (from EtOH or CHCl3). [Kikuchi et al. J Phys Chem 91 574 1987, Beilstein 6 III 2969, 6 IV 4257.]
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