| Identification | More | [Name]
6-Methoxytetralone | [CAS]
1078-19-9 | [Synonyms]
1(2H)-NAPHTHALENONE, 3,4-DIHYDRO-6-METHOXY-
3,4-DIHYDRO-6-METHOXY-1(2H)-NAPHTHALENONE
6-METHOXY-1,2,3,4-TETRAHYDRO-1-NAPHTHALENONE
6-METHOXY-1,2,3,4-TETRAHYDRO-1-NAPHTHONE
6-METHOXY-1,2,3,4-TETRAHYDRONAPHTHALEN-1-ONE
6-METHOXY-1-TETRALONE
6-METHOXY-3,4-DIHYDRO-2H-NAPHTHALEN-1-ONE
6-METHOXY-ALPHA-TETRALONE
6-METHOXY TETRALONE
METHOXY(6-)-1-TETRALONE
TIMTEC-BB SBB007549
3,4-dihydro-6-methoxy-1(2h)-naphthalenon
3,4-Dihydro-6-methoxy-1(2H)-napthalenone
6-Methoxy-3,4-dihydro-1(2H)-naphthalenone
6-Methoxy-tetalone
6-Metoxy-1-tetralone
6-Methoxy-1-Tetralon
6-METHOXYA-TETRALONE
6-Methoxy
6-Methoxy-l-tetralone | [EINECS(EC#)]
214-078-0 | [Molecular Formula]
C11H12O2 | [MDL Number]
MFCD00001695 | [Molecular Weight]
176.21 | [MOL File]
1078-19-9.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29145000 |
| Raw materials And Preparation Products | Back Directory | [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 |
| Hazard Information | Back Directory | [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%).  |
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