Product Introduction
| 6-methoxy-1-tetralone Basic information |
| Product Name: | 6-methoxy-1-tetralone |
| Synonyms: | 6-METHOXY-1,2,3,4-TETRAHYDRONAPHTHALEN-1-ONE;6-METHOXY-1,2,3,4-TETRAHYDRO-1-NAPHTHALENONE;6-METHOXY-1,2,3,4-TETRAHYDRO-1-NAPHTHONE;6-METHOXY-3,4-DIHYDRO-2H-NAPHTHALEN-1-ONE;6-METHOXY-1-TETRALONE;6-METHOXY TETRALONE;6-METHOXY-ALPHA-TETRALONE;TIMTEC-BB SBB007549 |
| CAS: | 1078-19-9 |
| MF: | C11H12O2 |
| MW: | 176.21 |
| EINECS: | 214-078-0 |
| Product Categories: | Ketone;C11 to C12;Carbonyl Compounds;Carbonyl Compounds;Ketones |
| Mol File: | 1078-19-9.mol |
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| 6-methoxy-1-tetralone Chemical Properties |
| Melting point | 77-79 °C (lit.) |
| Boiling point | 171 °C/11 mmHg (lit.) |
| density | 1.0558 (rough estimate) |
| refractive index | 1.5250 (estimate) |
| Fp | 171°C/11mm |
| storage temp. | Sealed in dry,Room Temperature |
| form | Fine Crystalline Powder |
| color | Yellow to light brown |
| PH | 5.96 at 23℃ and 10g/L |
| Merck | 14,6000 |
| BRN | 972739 |
| InChIKey | MNALUTYMBUBKNX-UHFFFAOYSA-N |
| CAS DataBase Reference | 1078-19-9(CAS DataBase Reference) |
| NIST Chemistry Reference | 1(2H)-Naphthalenone, 3,4-dihydro-6-methoxy-(1078-19-9) |
| EPA Substance Registry System | 1(2H)-Naphthalenone, 3,4-dihydro-6-methoxy- (1078-19-9) |
| Safety Information |
| Hazard Codes | Xn,Xi |
| Risk Statements | 22-36/37/38-20/21/22 |
| Safety Statements | 24/25-36-26 |
| WGK Germany | 3 |
| Hazard Note | Irritant |
| TSCA | Yes |
| HS Code | 29145000 |
| MSDS Information |
| Provider | Language |
|---|---|
| 6-Methoxytetralone | English |
| SigmaAldrich | English |
| ACROS | English |
| ALFA | English |
| 6-methoxy-1-tetralone Usage And Synthesis |
| Chemical Properties | yellow to light brown fine crystalline powder |
| Uses | 6-Methoxy-1-tetralone is a reagent useful in the synthesis of (2-(furanyl)vinyl)-1-tetralone chalcones which possesses anticancer agents and inducers of apoptosis. |
| Definition | ChEBI: 6-Methoxy-1-tetralone is a member of tetralins. |
| Preparation | (1) Reacting anisole with an acylating agent in Lewis acid and a solvent at the temperature of-10-40 ℃ to generate an intermediate 1, wherein the molar ratio of the Lewis acid to the acylating agent to the anisole is 1-10: 1-10: 1, the Lewis acid is selected from one or more of concentrated sulfuric acid, phosphoric acid, polyphosphoric acid, zinc chloride, aluminum trichloride, superacid and heteropoly acid; (2) the intermediate 1 does not need to be separated, the temperature is raised to 70-120 ℃, and the intermediate 1 continues to react to generate 6-methoxy-1-tetralone; (3) cooling the reaction product, adding water to stop the reaction, extracting, purifying and desolventizing to obtain a crude product of the 6-methoxy-1-tetralone, and refining the crude product by a solvent to obtain a high-purity product. |
| Synthesis Reference(s) | Journal of the American Chemical Society, 64, p. 94, 1942 DOI: 10.1021/ja01253a025 Tetrahedron Letters, 9, p. 2917, 1968 DOI: 10.1016/S0040-4039(00)89611-2 |
| Synthesis | The synthesis of 6-methoxy-1-tetralone is as follows:Eaton's reagent (1.00 mL, 5.31 mmol) was added slowly to a stirred solution of methyl 4-(3-methoxyphenyl)butanoate (4; 0.37g, 1.78 mmol) in DCE (1 mL). The resulting mixture was stirred at 75 °C for 2h under N2 atmosphere. Then, the reaction mixture was allowed to reach room temperature, and was poured over ice-water and extracted with EtOAc (3 × 15 mL). The combined organic extracts were washed successively with brine (2 × 15 mL) and H2O (2 × 20 mL), filtered over Na2SO4 and concentrated under reduced pressure. The resulting brownish oil was fractionated by column chromatography (silica gel, EtOAc-hexanes, 1:9) to obtain 6-methoxy-1-tetralone as ayellowish oil; yield: 0.28 g (91%).  |
| 6-methoxy-1-tetralone Preparation Products And Raw materials |
| Raw materials | FUMING SULFURIC ACID-->Detergent-->6-METHOXY-1,2,3,4-TETRAHYDRONAPHTHALENE |
| Preparation Products | 17-Ethinyl-17-hydroxy-18-methylestra-5(10),9(11)-dien-3-one-3-ethylene ketal-->3-Methoxy-18-methylestra-2,5(10)dien-17-one 17-ethylene ketal-->17-Ethinyl-3,17-dihydroxy-18-methylestra-2,5(10)-diene3-methylether-->3-Methoxy-18-methylestra-1,3,5(10),8-tetraen-17-ethylene ketal-->6-CYANO-1-TETRALONE-->6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one-->4-Methoxyphthalic acid-->2-Methoxy-6,7,8,9-tetrahydrobenzocyclohepten-5-one-->2-[2-(6-methoxytetralin-1-ylidene)-ethyl]-2-methylcyclopentane-1,3-dione -->1-CHLORO-6-METHOXY-3,4-DIHYDRO-NAPHTHALENE-2-CARBALDEHYDE-->7-METHOXY-4,5-DIHYDRO-NAPHTHO[1,2-D]THIAZOL-2-YLAMINE |
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