2-Tetralone

2-Tetralone
Structural formula of 2-tetralone
Ball-and-stick model of the 2-tetralone molecule
Names
Preferred IUPAC name
3,4-Dihydronaphthalen-2(1H)-one
Other names
β-Tetralone; 2-Tetralone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.727 Edit this at Wikidata
EC Number
  • 208-498-3
UNII
  • InChI=1S/C10H10O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4H,5-7H2 ☒N
    Key: KCKZIWSINLBROE-UHFFFAOYSA-N ☒N
  • InChI=1/C10H10O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4H,5-7H2
    Key: KCKZIWSINLBROE-UHFFFAOYAE
  • c1ccc2c(c1)CCC(=O)C2
Properties
C10H10O
Molar mass 146.189 g·mol−1
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
in basic water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[1][2]

2-Tetralone may be prepared by reductive cleavage of 2-naphthyl ethers.[3]

Applications

2-Tetralone is an intermediate in the synthesis of a variety of pharmaceutical drugs including L-687,384, nepinalone, napamezole,[4] spirodone, and trioxifene.

See also

References

  1. ^ 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.
  2. ^ 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.
  3. ^ 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
  4. ^ 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.