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6-methoxy-1-tetralone

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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;Ketones;Carbonyl Compounds
Mol File:1078-19-9.mol
6-methoxy-1-tetralone Structure
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
PH5.96 at 23℃ and 10g/L
Merck 14,6000
BRN 972739
InChI1S/C11H12O2/c1-13-9-5-6-10-8(7-9)3-2-4-11(10)12/h5-7H,2-4H2,1H3
InChIKeyMNALUTYMBUBKNX-UHFFFAOYSA-N
SMILESCOc1ccc2C(=O)CCCc2c1
CAS DataBase Reference1078-19-9(CAS DataBase Reference)
NIST Chemistry Reference1(2H)-Naphthalenone, 3,4-dihydro-6-methoxy-(1078-19-9)
EPA Substance Registry System1(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 TSCA listed
HS Code 29145000
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Aquatic Chronic 3
Skin Sens. 1B
MSDS Information
ProviderLanguage
6-Methoxytetralone English
SigmaAldrich English
ACROS English
ALFA English
6-methoxy-1-tetralone Usage And Synthesis
Chemical Propertiesyellow to light brown fine crystalline powder
Uses6-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.
DefinitionChEBI: 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
SynthesisThe 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%).    1078-19-9.png
Tag:6-methoxy-1-tetralone(1078-19-9) Related Product Information
Nabumetone 1-Tetralone (Trifluoromethoxy)benzene 2-Bromo-6-methoxynaphthalene 6-Methoxy-2-naphthaldehyde 7-Methoxy-1-tetralone 6,7-Dimethoxy-1-tetralone 7-Methoxy-2-tetralone 6,7-Dimethoxy-2-tetralone 5-Methoxy-3,4-dihydro-2H-naphthalen-1-one 5 8-DIMETHOXY-1-TETRALONE 99 5-Methoxy-2-tetralone 1,2,3,4-Tetrahydronaphthalene 6-METHOXY-1,2,3,4-TETRAHYDRONAPHTHALENE 6-METHOXY-2-METHYL-1-TETRALONE 6,7-(METHYLENEDIOXY)-1-TETRALONE dactylocycline B 3,11-DIMETHOXY-7-PHENYL-6,8,9,13B-TETRAHYDRO-5H-DIBENZO[C,H]XANTHYLIUM PERCHLORATE

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