530-93-8

Basic information

• Product Name: beta-Tetralone
• Synonyms: 2(1H)-Naphthalenone, 3,4-dihydro-;TETRALONE-2;2-TETRALONE 97%;3,4-DIHYDRO-2-OXONAPHTHALENE;3,4-Dihydro-2(1H)-naphthalenone, 3,4-Dihydro-2-naphthol;1,2,3,4-Tetrahydronaphthalene-2-one;2-Oxotetrahydronaphthalene;Tetralin-2-one
• CAS NO: 530-93-8
• Molecular Formula: C₁₀H₁₀O
• Molecular Weight: 146.19
• EINECS: 208-498-3
• Product Categories: Bioactive Small Molecules;Building Blocks;C10;Carbonyl Compounds;Cell Biology;Chemical Synthesis;Ketones;Organic Building Blocks;T;Aromatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 530-93-8.mol

Chemical Properties

• Melting Point: 18 °C(lit.)
• Boiling Point: 131 °C11 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear pale yellow/Liquid or Low Melting Solid
• Density: 1.106 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0459mmHg at 25°C
• Refractive Index: n20/D 1.560(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: insoluble
• Sensitive: Air Sensitive
• BRN: 509386
• CAS DataBase Reference: beta-Tetralone(CAS DataBase Reference)
• NIST Chemistry Reference: beta-Tetralone(530-93-8)
• EPA Substance Registry System: beta-Tetralone(530-93-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 530-93-8(Hazardous Substances Data)

Usage

Uses

Used in Fossil Fuel Industry:
Beta-Tetralone is used as a biological marker for the identification and analysis of fossil fuels. Its presence in fossil fuels can provide valuable information about the source and composition of the fuels, aiding in their exploration, extraction, and refining processes.
Used in Environmental Science:
Beta-Tetralone is used as a biomarker in environmental studies to detect and monitor the presence of fossil fuel contaminants in soil, water, and air. Its detection can help in assessing the extent of pollution and the effectiveness of remediation efforts.
Used in Chemical Research:
Beta-Tetralone is used as a research compound in the field of organic chemistry. Its unique structure and properties make it a valuable tool for studying various chemical reactions and mechanisms, as well as for the synthesis of new compounds and materials.

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.]

InChI:InChI=1/C10H10O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-4H,5-7H2

Upstream product

• 110-86-1 pyridine 
• 64245-04-1 2-bromo-1-hydroxy-1,2,3,4-tetrahydronaphthalene 
• 91-22-5 quinoline 
• 103039-11-8 1,2,3,4-tetrahydronaphthalene-2,3-chlorohydrin 
• 93-04-9 2-Methoxynaphthalene 
• 93-18-5 2-ethoxynaphthalene 
• 40815-23-4 3-methoxy-1,2-dihydronaphthalene 
• 66530-07-2 ethyl 2-oxo-1,2,3,4-tetrahydronaphthalene-1-carboxylate 
• 530-91-6 1,2,3,4-tetrahydronaphthalen-2 ol 
• 109404-82-2 (+/-)-cis-3-(toluene-4-sulfonyloxy)-1,2,3,4-tetrahydro-[2]naphthol 
• 135-19-3 β-naphthol 
• 2461-35-0 2,3-epoxy-1,2,3,4-tetrahydronaphthalene 
• 2417-93-8 propyllithium 
• 2461-34-9 1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirene 

Downstream Products

• 102664-85-7 1,3-dibenzylidene-3,4-dihydro-1H-naphthalen-2-one 
• 71912-62-4 1-phenethyl-3,4-dihydro-1H-naphthalen-2-one 
• 110048-65-2 1-(2-benzyloxy-ethyl)-3,4-dihydro-1H-naphthalen-2-one 
• 194-59-2 7H-dibenzo[c,g]carbazole 
• 4024-14-0 1-methyl-2-tetralone 
• 17724-38-8 1,2,4,5-tetrahydro-3H-benzo[c]azepin-3-one 
• 15987-50-5 1,3,4,5-tetrahydro-2H-benzo[d]azepin-2-one 
• 3349-65-3 2-tetralone oxime 
• 776-79-4 2-(2-carboxyethyl)benzoic acid 
• 61034-42-2 1-benzyl-3,4-dihydro-1H-naphthalen-2-one 
• 6331-63-1 2-amino-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid 
• 135-19-3 β-naphthol 
• 93648-51-2 1,2,3,4-tetrahydro-[2]naphthaldehyde phenylhydrazone 
• 29122-10-9 4-phenyl-8-(1,2,3,4-tetrahydro-naphthalen-2-yl)-1-oxa-3,8-diaza-spiro[4.5]decan-2-one 

Relevant articles and documents

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