beta-Tetralone Property

Melting point:

18 °C(lit.)

Boiling point:

131 °C11 mm Hg(lit.)

Density 

1.106 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.560(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Liquid or Low Melting Solid

color 

Clear pale yellow

Water Solubility 

insoluble

Sensitive 

Air Sensitive

BRN 

509386

InChIKey

KCKZIWSINLBROE-UHFFFAOYSA-N

CAS DataBase Reference

530-93-8(CAS DataBase Reference)

NIST Chemistry Reference

2(1H)-Naphthalenone, 3,4-dihydro-(530-93-8)

EPA Substance Registry System

2-Tetralone (530-93-8)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36

WGK Germany 

3

F 

10

TSCA 

Yes

HS Code 

29143900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H372Causes damage to organs through prolonged or repeated exposure

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

beta-Tetralone Chemical Properties,Usage,Production

Chemical Properties

Liquid colorless to yellow

Uses

β-Tetralone is the 2-keto derivative of Tetralin. β-Tetralone was initially reported to be a metabolite of Tetralin but was later found to be just an artifact in the metabolism process. β-Tetralone is known to be biological marker in fossil fuels.

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 4232, 1961 DOI: 10.1021/jo01069a014

Purification Methods

If reasonably pure, then fractionate it through an efficient column. Otherwise purify it via the bisulfite adduct. To a solution of NaHSO3 (32.5g, 0.31mol) in H2O (57mL) is added 95% EtOH (18mL) and set aside overnight. Any bisulfite-sulfate that separated is removed by filtration, and the filtrate is added to the tetralone (14.6g, 0.1mol) and shaken vigorously. The adduct separates in a few minutes as a white precipitate and is kept on ice for ~3.5hours with occasional shaking. The precipitate is collected, washed with 95% EtOH (13mL), then with Et2O (4 x 15mL, by stirring the suspension in the solvent, filtering and repeating the process). The colourless product is dried in air and stored in air tight containers in which it is stable for extended periods (yield is ~17g). This bisulfite (5g) is suspended in H2O (25mL), and Na2CO3.H2O (7.5g) is added (pH of solution is ~10). The mixture is then extracted with Et2O (5 x 10mL, i.e. until the aqueous phase does not test for tetralone — see below). Wash the combined extracts with 10% aqueous HCl (10mL), H2O (10mL, i.e. until the washings are neutral), dry (MgSO4), filter, evaporate and distil the residual oil using a Claisen flask under reduced pressure and in a N2 atmosphere. The pure tetralone is a colourless liquid b 70-71o/0.25mm (see also above). The yield is ~2g. Tetralone test: Dissolve a few drops of the tetralone solution (ethereal or aqueous) in 95% EtOH in a test tube and add 10 drops of 25% NaOH down the side of the tube. A deep blue colour develops at the interface with air. [Soffer et al. Org Synth Coll Vol IV 903 1963, Cornforth et al. J Chem Soc 689 1942, UV: Soffer et al. J Am Chem Soc 1556 1952.] The phenylhydrazone has m 108o [Crawley & Robinson J Chem Soc 2001 1938]. [Beilstein 7 H 370, 7 II 295, 7 III 1422, 7 IV 1018.]