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Preferred IUPAC name 3,4-Dihydronaphthalen-2(1H)-one | |
Other names β-Tetralone; 2-Tetralone | |
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ECHA InfoCard | 100.007.727 |
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Properties | |
Chemical formula | C10H10O |
Molar mass | 146.189 g·mol |
Appearance | Colourless liquid |
Density | 1.106 g/mL |
Melting point | 18 °C (64 °F; 291 K) |
Boiling point | 70–71 °C (158–160 °F; 343–344 K) /0.25 mm |
Solubility in water | in basic water |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references |
2-Tetralone is an organic chemical compound with the molecular formula C10H10O. This colourless oil is an intermediate in organic synthesis. It is a ketone derivative of tetralin, a hydrogenated derivative of naphthalene.
History and synthesis
The compound was first obtained by Eugen Bamberger and Wilhelm Lodter in 1893 by dehydrohalogenation of 3-chloro-2-tetralol with hot alkali.
2-Tetralone may be prepared by reductive cleavage of 2-naphthyl ethers.
Applications
2-Tetralone is an intermediate in the synthesis of a variety of pharmaceutical drugs including L-687,384, nepinalone, napamezole, spirodone, and trioxifene.
See also
References
- Shner, V. F.; Przhiyaglovskaya, N. M. (1966-07-31). "COMPOUNDS OF THE β-TETRALONE SERIES". Russian Chemical Reviews. 35 (7): 523. doi:10.1070/RC1966v035n07ABEH001493. ISSN 0036-021X.
- Bamberger, Eug.; Lodter, W. (1893). "Ueber das Dihydronaphtalin und einige seiner Derivate". Berichte der deutschen chemischen Gesellschaft (in German). 26 (2): 1833–1844. doi:10.1002/cber.189302602133. ISSN 1099-0682.
- M. D. Soffer, M. P. Bellis, Hilda E. Gellerson, and Roberta A. Stewart "β-Tetralone" Org. Synth. 1952, 32, 97 doi:10.15227/orgsyn.032.0097
- Wentland, Mark P.; Bailey, Denis M.; Alexander, E. John; Castaldi, Michael J.; Ferrari, Richard A.; Haubrich, Dean R.; Luttinger, Daniel A.; Perrone, Mark H. (1987). "Synthesis and antidepressant properties of novel 2-substituted 4,5-dihydro-1H-imidazole derivatives". Journal of Medicinal Chemistry. 30 (8): 1482–1489. doi:10.1021/jm00391a034. PMID 3039138.