2',3',4'-TRIMETHOXYACETOPHENONE Chemical Properties

Melting point:

14-15 °C(lit.)

Boiling point:

295-297 °C(lit.)

Density 

1.155 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.5384(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light yellow to Light orange

LogP

1.630

CAS DataBase Reference

13909-73-4(CAS DataBase Reference)

EPA Substance Registry System

2',3',4'-Trimethoxyacetophenone (13909-73-4)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

RTECS 

AN0531000

Hazard Note 

Irritant

HS Code 

29145000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

2',3',4'-TRIMETHOXYACETOPHENONE Usage And Synthesis

Chemical Properties

clear yellow liquid

Uses

2',3',4'-Trimethoxyacetophenone is an organic compound with a benzene ring and an acetyl group. 2',3',4'-Trimethoxyacetophenone can be used as a raw material for synthesizing dyes, fragrances, and certain pesticides[1].

Preparation

Obtained by reaction of dimethyl sulfate with gallacetophenone in methanol in the presence of potassium hydroxide.

General Description

2′,3′,4′-Trimethoxyacetophenone on reaction with BCl₃ gives the corresponding 2,3-dihydroxy-4-methoxy compounds.

Synthesis

To a solution of 2',3',4'-trihydroxyacetophenone (1.66 g, 10 mmol) in acetone (50 mL) was added potassium carbonate (11 g) and dimethyl sulfate (6 mL, 30 mmol). The reaction was stirred at 45 °C for 17 h. The reaction was terminated by the addition of water. The reaction mixture was filtered, neutralized with 1 M HCl and then extracted with dichloromethane (200 mL). The organic layer was washed with brine (150 mL) and the crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 5:1). Yield: 1.85 g (88%).1H NMR (CDCl3, 300 MHz) δ 7.50 (d, J = 8.8 Hz, 1H), 6.68 (d, J = 8.8 Hz, 1H), 3.94 (s, 3H), 3.89 (s, 3H), 3.85 (s, 3H), 2.58 (s, 3H) ppm.13C NMR ( CDCl3, 75 MHz) δ 198.01, 157.44, 154.30, 128.99, 125.78, 125.57, 106.99, 61.30, 60.80, 56.06, 30.97 ppm. Pharm. Bull. 1984, 32, 3354-3360.

References

[1] Lenz G R, et al. Synthesis of the novel isoquinoline enamide alkaloid polycarpine[J]. Journal of Heterocyclic Chemistry, 1981, 18(4): 691-693.

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