2-Tetralone

2-Tetralone
Names
	Preferred IUPAC name 3,4-Dihydronaphthalen-2(1H)-one
	Other names β-Tetralone; 2-Tetralone
Identifiers
CAS Number	530-93-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	61564 ;
ECHA InfoCard	100.007.727
EC Number	208-498-3;
PubChem CID	68266;
UNII	K46ZZ833BH ;
CompTox Dashboard (EPA)	DTXSID0060193 ;
	InChI InChI=1S/C10H10O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4H,5-7H2 Key: KCKZIWSINLBROE-UHFFFAOYSA-N ; InChI=1/C10H10O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4H,5-7H2 Key: KCKZIWSINLBROE-UHFFFAOYAE;
	SMILES c1ccc2c(c1)CCC(=O)C2;
Properties
Chemical formula	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
Solubility in water	in basic water
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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.^[1]^[2]

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

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

^ 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.