2-Methoxynaphthalene

2-Methoxynaphthalene
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
  • InChI=1S/C11H10O/c1-12-11-7-6-9-4-2-3-5-10(9)8-11/h2-8H,1H3
    Key: LUZDYPLAQQGJEA-UHFFFAOYSA-N
  • InChI=1/C11H10O/c1-12-11-7-6-9-4-2-3-5-10(9)8-11/h2-8H,1H3
    Key: LUZDYPLAQQGJEA-UHFFFAOYAR
  • O(c2ccc1c(cccc1)c2)C
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

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.

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.

References

  1. ^ a b c "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.
  6. ^ (page 987) Furniss, B. S., Vogel, A. I., eds. (1989). Vogel’s textbook of practical organic chemistry (New. ed., 5. ed., rev. [Nachdr.] ed.). Pearson/Prentice Hall. ISBN 9780582462366.
  7. ^ a b (Chapter 8) Isac-García, J., Dobado, J. A., Calvo-Flores, F. G., Martínez-García, H. (2016). "Experimental Organic Chemistry". Organic Synthesis Experiments. Elsevier. pp. 239–289. doi:10.1016/B978-0-12-803893-2.50008-5.
  8. ^ "2-ACETYL-6-METHOXYNAPHTHALENE". Organic Syntheses. 53: 5. 1973. doi:10.15227/orgsyn.053.0005. Retrieved 17 January 2026.
  9. ^ Harrison, I. Thomas., Lewis, Brian., Nelson, Peter., Rooks, Wendell., Roszkowski, Adolph., Tomolonis, Albert., Fried, J. H. (March 1970). "Nonsteroidal antiinflammatory agents. I. 6-Substituted 2-naphthylacetic acids". Journal of Medicinal Chemistry. 13 (2): 203–205. doi:10.1021/jm00296a008.
  10. ^ 林晓辉, 杨庆垂, & 淡勇德, CN111333494 (2023 to Wuhan Haixin Pharmaceutical Research Co ltd).
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