β-Naphthol methyl ether

β-Naphthol methyl ether
Names
	Preferred IUPAC name 2-Methoxynaphthalene
	Other names Methyl naphthalen-2-yl ether; Methyl 2-naphthyl ether; 2-Naphthol methyl ether; 2-Naphthyl methyl ether; β-Methoxynaphthalene; β-Methyl naphthyl ether; β-Naphthol methyl ether; Nerolin; Yara yara
Identifiers
CAS Number	93-04-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	6852;
ECHA InfoCard	100.002.013
PubChem CID	7119;
UNII	VX2T1Z50C4 ;
CompTox Dashboard (EPA)	DTXSID7044392 ;
	InChI 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;
	SMILES O(c2ccc1c(cccc1)c2)C;
Properties
Chemical formula	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

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.

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]

References

^ ^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-methoxynaphthalene", The Good Scents Company, 2012
^ 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.
^ 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.
^ Mann, Frederick George (1952). Practical Organic Chemistry. Longmans, Green & Co. p. 175.

[iupac2013-1] "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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