6-methoxy-1-tetralone
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
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)
- Flash point:
- 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
- Language:English Provider:6-Methoxytetralone
- Language:English Provider:SigmaAldrich
- Language:English Provider:ACROS
- Language:English Provider:ALFA
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
Preparation Products
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6-methoxy-1-tetralone(1078-19-9)Related Product Information
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