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2-Methoxynaphthalene

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2-Methoxynaphthalene Basic information

Product Name:
2-Methoxynaphthalene
Synonyms:
  • Naproxen Impurity 13(Naproxen EP Impurity M)
  • 2-Methoxynaphthaleneodium salt hydrate
  • NEROLINE YARA YARA
  • NEROLIN YARA YARA
  • NAPROXEN IMP M
  • 2-NAPHTHYL METHYL ETHER
  • 2-METHOXYNAPHTHALENE
  • methyl β-naphthyl ether
CAS:
93-04-9
MF:
C11H10O
MW:
158.2
EINECS:
202-213-6
Product Categories:
  • Aromatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
  • Aromatics
  • Food & Feed ADDITIVES
  • Impurities
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Naphthalene derivatives
  • 93-04-9
Mol File:
93-04-9.mol
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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℃
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)
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Safety Information

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

MSDS

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2-Methoxynaphthalene Usage And Synthesis

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.]

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