β-Naphthol methyl ether

β-Naphthol methyl ether, also called 2-methoxynaphthalene 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.

β-Naphthol methyl ether
Names
Preferred IUPAC name
2-Methoxynaphthalene[1]
Other names
Methyl naphthalen-2-yl ether[1]
Methyl 2-naphthyl ether[1]
2-Naphthol methyl ether
2-Naphthyl methyl ether
β-Methoxynaphthalene
β-Methyl naphthyl ether
β-Naphthol methyl ether
Nerolin
Yara yara
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.013
UNII
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).
Infobox references

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. It has a faint but persistent odor and used to be a scented compound found in soap and other products.[5]

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References
  1. "CHAPTER P-6. Applications to Specific Classes of Compounds". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 703. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
  2. "2-methoxynaphthalene", The Good Scents Company, 2012
  3. Cavrini V, Roveri P, Gatti R, Ferruzzi C, Panico AM, Pappalardo MS (1982). "Synthesis of 2-methoxynaphthalene derivatives as potential anti-inflammatory agents". Farmaco Sci (in Italian). 37 (3): 171–178. PMID 7067812.
  4. Mohapatra, Himansu; Umapathy, S. (2010). "Time-Resolved Resonance Raman Studies on Proton-Induced Electron-Transfer Reaction from Triplet Excited State of 2-Methoxynaphthalene to Decafluorobenzophenone". The Journal of Physical Chemistry A. 114 (47): 12447–12451. Bibcode:2010JPCA..11412447M. doi:10.1021/jp109821r. PMID 21058635.
  5. Mann, Frederick George (1952). Practical Organic Chemistry. Longmans, Green & Co. p. 175.
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