beta-Tetralone
Synonym(s):3,4-Dihydro-2(1H)-naphthalenone;3,4-Dihydro-2-naphthol;beta-Tetralone
- CAS NO.:530-93-8
- Empirical Formula: C10H10O
- Molecular Weight: 146.19
- MDL number: MFCD00001727
- EINECS: 208-498-3
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-12-18 13:37:16
What is beta-Tetralone?
Chemical properties
Liquid colorless to yellow
The Uses of beta-Tetralone
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.]
Properties of beta-Tetralone
Melting point: | 18 °C(lit.) |
Boiling point: | 131 °C11 mm Hg(lit.) |
Density | 1.106 g/mL at 25 °C(lit.) |
refractive index | n |
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 |
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 information for beta-Tetralone
Signal word | Danger |
Pictogram(s) |
Exclamation Mark Irritant GHS07 Health Hazard GHS08 Environment GHS09 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H372:Specific target organ toxicity, repeated exposure H410:Hazardous to the aquatic environment, long-term hazard |
Precautionary Statement Codes |
P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P391:Collect spillage. Hazardous to the aquatic environment P501:Dispose of contents/container to..… |
Computed Descriptors for beta-Tetralone
InChIKey | KCKZIWSINLBROE-UHFFFAOYSA-N |
beta-Tetralone manufacturer
Sri Neelima Laboratories
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