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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
  • 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)
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)
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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

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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%).   

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