1-(4,5-DIMETHOXY-2-NITRO-PHENYL)-ETHANONE Chemical Properties

Melting point:

133.5-135 °C

Boiling point:

389.2±37.0 °C(Predicted)

Density 

1.245±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

Light orange to Yellow to Green

InChI

InChI=1S/C10H11NO5/c1-6(12)7-4-9(15-2)10(16-3)5-8(7)11(13)14/h4-5H,1-3H3

InChIKey

ZVLFGESHYMKNQP-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC(OC)=C(OC)C=C1[N+]([O-])=O)C

EPA Substance Registry System

Ethanone, 1-(4,5-dimethoxy-2-nitrophenyl)- (4101-32-0)

Safety Information

HS Code 

2913.00.4000

1-(4,5-DIMETHOXY-2-NITRO-PHENYL)-ETHANONE Usage And Synthesis

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 1585, 1990 DOI: 10.1021/jo00292a038

Synthesis

General procedure for the synthesis of 1-(4,5-dimethoxy-2-nitrophenyl)ethanone from 3,4-dimethoxyacetophenone: (1) Nitration step: a solution was prepared by dissolving 3,4-dimethoxyacetophenone (1,500 g) in 17% nitric acid (1,400 g) at 5 to 10 °C, followed by slow dropwise addition to a solution consisting of 67% nitric acid (8430 g) and sodium nitrite (18 g) (18 g). The titration process was controlled to be completed within 2 to 3 hours. After the dropwise addition, the reaction solution was continued to be stirred at 5 to 10°C for 1 to 2 hours. Cold water (7.5 L) was added to dilute the reaction mixture and stirred for 30 minutes. The reaction mixture was filtered and the filter cake was washed with water (30 L). The solid product obtained by filtration was re-suspended in water (7.5 L), neutralized with aqueous sodium bicarbonate to pH neutral, filtered again and washed with water (7 L). Finally, the product was dried under reduced pressure to afford 3,4-dimethoxy-6-nitroacetophenone (2164 g, 87.9% yield). The structure of the product was confirmed by 1H-NMR (400 MHz, CDCl3): δ 2.50 (s, 3H), 3.97 (s, 3H), 3.99 (s, 3H), 6.76 (s, 1H), 7.62 (s, 1H).

References

[1] Patent: EP1559715, 2005, A1. Location in patent: Page/Page column 17
[2] Heterocycles, 2016, vol. 92, # 10, p. 1882 - 1887
[3] Chemistry Letters, 2000, # 7, p. 712 - 713
[4] Patent: EP3205650, 2017, A1. Location in patent: Paragraph 0106; 0354; 0355
[5] Journal of Organic Chemistry, 1999, vol. 64, # 21, p. 7988 - 7995

1-(4,5-DIMETHOXY-2-NITRO-PHENYL)-ETHANONE(4101-32-0)Related Product Information

• 1-(3,4,5-Trimethoxy-2-nitrophenyl)ethanone
• 1-(4,5-DIMETHOXY-2-NITRO-PHENYL)-ETHANONE
• (4-CHLORO-PHENYL)-(4,5-DIMETHOXY-2-NITRO-PHENYL)-METHANONE
• 2-BROMO-1-(4,5-DIMETHOXY-2-NITRO-PHENYL)ETHANONE
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• (4,5-DIMETHOXY-2-NITRO-PHENYL)-(5-METHYL-FURAN-2-YL)-METHANONE
• FURAN-2-YL-(7-NITRO-2,3-DIHYDRO-BENZO[1,4]DIOXIN-6-YL)-METHANONE
• 1-(4,5-DIMETHOXY-2-NITRO-PHENYL)-2-PHENYL-ETHANONE
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• (2,4-DICHLORO-PHENYL)-(4,5-DIMETHOXY-2-NITRO-PHENYL)-METHANONE
• (7-NITRO-2,3-DIHYDRO-BENZO[1,4]DIOXIN-6-YL)-P-TOLYL-METHANONE
• (4-BROMO-PHENYL)-(4,5-DIMETHOXY-2-NITRO-PHENYL)-METHANONE
• (3-BROMO-PHENYL)-(7-NITRO-2,3-DIHYDRO-BENZO[1,4]DIOXIN-6-YL)-METHANONE
• 1-(7-NITRO-2,3-DIHYDRO-BENZO[1,4]DIOXIN-6-YL)-ETHANONE
• (4,5-DIMETHOXY-2-NITRO-PHENYL)-PHENYL-METHANONE
• (4,5-DIMETHOXY-2-NITRO-PHENYL)-P-TOLYL-METHANONE