METHYL HOMOVERATRATE Chemical Properties

Boiling point:

175℃ (15 Torr)

Density 

1.105±0.06 g/cm3 (20 ºC 760 Torr)

refractive index 

1.5253 (23℃)

Flash point:

121.6±23.2℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Oil

color 

Colourless

EPA Substance Registry System

Benzeneacetic acid, 3,4-dimethoxy-, methyl ester (15964-79-1)

METHYL HOMOVERATRATE Usage And Synthesis

Uses

Methyl Homoveratrate can be used as entry inhibitors against H5N1.

Synthesis

General procedure for the synthesis of methyl 3,4-dimethoxyphenylacetate from methanol and 3,4-dimethoxyphenylacetic acid: 3,4-dimethoxyphenylacetic acid (25.0 g, 127.4 mmol) was dissolved in methanol (100 mL) in a 500 mL round-bottomed flask and a catalytic amount of sulfuric acid (about 10 drops) was added. The reaction mixture was stirred overnight under reflux conditions. After completion of the reaction, it was cooled to room temperature and methanol was removed by distillation under reduced pressure at 40 °C. The crude product was dissolved in dichloromethane (250 mL), washed sequentially with water (5 x 20 mL) and saturated saline (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give methyl 3,4-dimethoxyphenylacetate (25.77 g, 96% yield) as an orange oil. Molecular weight: 210.23; yield: 96%; Rf value: 0.25 (cyclohexane:ethyl acetate=3:1). 1H-NMR (CDCl3, δ): 3.56 (s, 2H, CH2), 3.70 (s, 3H, CH3), 3.87 (s, 3H, OCH3), 3.88 (s, 3H, OCH3), 6.82-6.83 (m , 3H, ArH).13C-NMR (CDCl3, δ): 40.6, 51.9, 55.8 (2 × C), 111.2, 112.4, 121.4, 126.4, 148.2, 148.9, 172.2.MS-ESI m/z (% relative abundance): 233.2 ([M+Na]+, 3), 151.1 ( 100).

References

[1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 1, p. 85 - 90
[2] Tetrahedron, 2007, vol. 63, # 46, p. 11377 - 11385
[3] Tetrahedron, 2013, vol. 69, # 42, p. 8914 - 8920
[4] Patent: US2012/214837, 2012, A1. Location in patent: Page/Page column 23-24
[5] Journal of Organic Chemistry, 2003, vol. 68, # 3, p. 1165 - 1167

METHYL HOMOVERATRATE(15964-79-1)Related Product Information

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• METHYL HOMOVERATRATE
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• METHYL 2-(4,5-DIMETHOXY-2-(((3-(TRIFLUOROMETHYL)PHENYL)AMINO)SULFONYL)PHENYL)ACETATE
• METHYL 2-(2-(((2-FLUORO-5-(TRIFLUOROMETHYL)PHENYL)AMINO)SULFONYL)-4,5-DIMETHOXYPHENYL)ACETATE
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• AKOS AU36-M281
• METHYL 2-(2-((4-(3-CHLORO-5-(TRIFLUOROMETHYL)(2-PYRIDYL))PIPERAZINYL)SULFONYL)-4,5-DIMETHOXYPHENYL)ACETATE