2-Methoxynaphthalene Property

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℃

refractive index 

1.5440 (estimate)

FEMA 

4704 | BETA-NAPHTHYL METHYL ETHER

Flash point:

272-274°C

storage temp. 

Sealed in dry,Room Temperature

solubility 

H2O: soluble (completely)

form 

Crystalline Solid

pka

0[at 20 ℃]

color 

White to yellow-brown

Odor

at 1.00 % in dipropylene glycol. sweet naphthyl floral orange blossom acacia neroli

Odor Type

naphthyl

Water Solubility 

INSOLUBLE

Merck 

14,5997

JECFA Number

1257

BRN 

1859408

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

InChIKey

LUZDYPLAQQGJEA-UHFFFAOYSA-N

LogP

3.318 at 25℃

CAS DataBase Reference

93-04-9(CAS DataBase Reference)

NIST Chemistry Reference

Naphthalene, 2-methoxy-(93-04-9)

EPA Substance Registry System

Naphthalene, 2-methoxy- (93-04-9)

Safety

Safety Statements 

22-24/25

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

2

RTECS 

QJ9468750

TSCA 

Yes

HS Code 

29093090

Toxicity

LD50 oral in rat: > 5gm/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

P391Collect spillage. Hazardous to the aquatic environment

2-Methoxynaphthalene Chemical Properties,Usage,Production

Description

β-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 Properties

white powder

Chemical Properties

Methyl 2-Naphthyl Ether forms white crystals (mp 73–74°C) with an intense orange blossom odor.

Chemical Properties

β-Naphthyl methyl ether has an intensely sweet, floral odor suggestive of orange blossoms; free from naphthol by-odor. It has a sweet, strawberry taste

Uses

2-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.

Uses

2-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.

Uses

2-Methoxynaphthalene is an Impurity of the non-steroidal anti-inflammatory Naproxen (N377525).

Definition

ChEBI: 2-Methoxynaphthalene is a member of naphthalenes.

Preparation

From postassium β-naphthol and methyl chloride at 300°C; by methylation of β-naphthlol with dimethyl sulfate or by direct esterification with methyl alcohol

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 Explosibility

Not classified

Synthesis

Preparation 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:

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 Methods

Fractionally 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.]