2-Methoxynaphthalene
Chemical compound
From Wikipedia, the free encyclopedia
2-Methoxynaphthalene, also called β-naphthol methyl ether, nerolin, or yara yara,[2] is a stabilizer found in gunpowder, particularly smokeless gunpowders. It is soluble in alcohol, and insoluble in water and dipropylene glycol.
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| Names | |
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| Preferred IUPAC name
2-Methoxynaphthalene[1] | |
| Other names | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.002.013 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C11H10O | |
| Molar mass | 158.200 g·mol−1 |
| Melting point | 73–75 °C (163–167 °F; 346–348 K) |
| Boiling point | 274 °C (525 °F; 547 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Studies have also been done on the antiinflammatory effect of β-naphthol methyl ether[3] and on how it behaves in time-resolved resonance Raman studies.[4]
Synthesis and uses
Nerolin can be prepared by alkylation of β-naphthol with dimethyl sulfate.[5][6]
Alternative syntheses rely on the reaction of 2-Naphthol with iodomethane and KOH (Williamson ether synthesis),[7] or by the reaction with methanol in concentrated sulfuric acid solution.[7]
It has a faint but persistent odor and used to be a scented compound found in soap and other products.
Applications
The Friedel–Crafts acylation with propionyl chloride gives 2-propionyl-6-methoxynaphthalene (Promen) [2700-47-2]. This compound has known uses in the synthesis of Doisynoestrol & Methallenestril.
Acetylation gives 2-Acetyl-6-methoxynaphthalene,[8] which has historical use in the synthesis of Naproxen.[9]
Nerolin had found use in the synthesis of 6-Methoxy-1-tetralone [1078-19-9],[10] which is a critical compound for manifold reasons.