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2-Methoxynaphthalene
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2-Methoxynaphthalene Structural Formula V1.svg 200px 2-Methoxynaphthalene Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) The Royal Society of Chemistry 2014 Cambridge 703 10.1039/9781849733069-00648 978-0-85404-182-4 CHAPTER P-6. Applications to Specific Classes of Compounds Methyl naphthalen-2-yl etherMethyl 2-naphthyl ether2-Naphthol methyl ether2-Naphthyl methyl etherβ-Methoxynaphthaleneβ-Methyl naphthyl etherβ-Naphthol methyl etherNerolinYara yara 93-04-9 correct CAS VX2T1Z50C4 correct FDA 7119 6852 O(c2ccc1c(cccc1)c2)C 1/C11H10O/c1-12-11-7-6-9-4-2-3-5-10(9)8-11/h2-8H,1H3 LUZDYPLAQQGJEA-UHFFFAOYAR 1S/C11H10O/c1-12-11-7-6-9-4-2-3-5-10(9)8-11/h2-8H,1H3 LUZDYPLAQQGJEA-UHFFFAOYSA-N
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2-Methoxynaphthalene, also called β-naphthol methyl ether, nerolin, or yara yara,"2-methoxynaphthalene", The Good Scents Company, 2012 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 Cavrini V, Roveri P, Gatti R, Ferruzzi C, Panico AM, Pappalardo MS 7067812 Synthesis of 2-methoxynaphthalene derivatives as potential anti-inflammatory agents 1982 Farmaco Sci 37 3 171–178 it and on how it behaves in time-resolved resonance Raman studies. 10.1021/jp109821r 21058635 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 2010 Mohapatra Himansu Umapathy S. 2010JPCA..11412447M
Synthesis and uses
Nerolin can be prepared by alkylation of β-naphthol with dimethyl sulfate.Practical Organic Chemistry Mann Frederick George Longmans, Green & Co 1952 175(page 987) ((Furniss, B. S.)), ((Vogel, A. I.)) 1989 Vogel’s textbook of practical organic chemistry Pearson/Prentice Hall New. ed., 5. ed., rev. [Nachdr.] 9780582462366
Alternative syntheses rely on the reaction of 2-Naphthol with iodomethane and KOH (Williamson ether synthesis),(Chapter 8) ((Isac-García, J.)), ((Dobado, J. A.)), ((Calvo-Flores, F. G.)), ((Martínez-García, H.)) 2016 Experimental Organic Chemistry Organic Synthesis Experiments Elsevier 239–289 https://linkinghub.elsevier.com/retrieve/pii/B9780128038932500085 10.1016/B978-0-12-803893-2.50008-5 or by the reaction with methanol in concentrated sulfuric acid solution.
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,Organic Syntheses 2-ACETYL-6-METHOXYNAPHTHALENE 53 5 1973 http://orgsyn.org/demo.aspx?prep=CV6P0034 10.15227/orgsyn.053.0005 free 17 January 2026 subscription which has historical use in the synthesis of Naproxen.((Harrison, I. Thomas.)), ((Lewis, Brian.)), ((Nelson, Peter.)), ((Rooks, Wendell.)), ((Roszkowski, Adolph.)), ((Tomolonis, Albert.)), ((Fried, J. H.)) Journal of Medicinal Chemistry Nonsteroidal antiinflammatory agents. I. 6-Substituted 2-naphthylacetic acids 13 2 203–205 March 1970 https://pubs.acs.org/doi/abs/10.1021/jm00296a008 10.1021/jm00296a008 subscription
Nerolin had found use in the synthesis of 6-Methoxy-1-tetralone [1078-19-9],林晓辉, 杨庆垂, & 淡勇德, CN111333494 (2023 to Wuhan Haixin Pharmaceutical Research Co ltd). which is a critical compound for manifold reasons.
References
Category:Naphthol ethers
Category:2-Naphthyl compounds