Ethyl 1-methyl-4-nitroimidazole-2-carboxylate Chemical Properties

Melting point:

128-130°

Boiling point:

350.7±34.0 °C(Predicted)

Density 

1.42±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

-2.47±0.60(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C7H9N3O4/c1-3-14-7(11)6-8-5(10(12)13)4-9(6)2/h4H,3H2,1-2H3

InChIKey

QGTGFMLXIBQONB-UHFFFAOYSA-N

SMILES

C1(C(OCC)=O)N(C)C=C([N+]([O-])=O)N=1

Safety Information

HS Code 

2933299090

Ethyl 1-methyl-4-nitroimidazole-2-carboxylate Usage And Synthesis

Uses

Ethyl 1-methyl-4-nitroimidazole-2-carboxylate

Uses

Terameprocol is a semi-synthetic lignan which inhibits the transcription of several inflammatory and oncogenic genes.

Synthesis

General procedure for the synthesis of ethyl N-methyl-4-nitro-1H-imidazole-2-carboxylate from ethyl 1-methylimidazole-2-carboxylate: ethyl 1-methylimidazole-2-carboxylate (1.8 g) was dissolved in concentrated sulfuric acid (5 mL) and the solution was cooled to 0 °C. 90% nitric acid (5 mL) was added slowly with stirring, followed by gradually warming the reaction mixture to room temperature and refluxing the reaction for 1.5 hours at -20 °C. Upon completion of the reaction, the mixture was poured into ice (50 mL) to quench the reaction. The reaction mixture was extracted with dichloromethane and the organic phase was dried over anhydrous sodium sulfate and subsequently concentrated under reduced pressure to give the crude product. The crude product was recrystallized using a mixture of carbon tetrachloride and ethanol solvents (1:1, 5 mL) to give ethyl N-methyl-4-nitro-1H-imidazole-2-carboxylate in the form of white crystals. The yield was 1.0543 g with 45% yield. The structure of the product was confirmed by 1H NMR (DMSO-d6) and 13C NMR (DMSO-d6): 1H NMR (DMSO-d6): δ 8.61 (s, 1H), 4.33 (q, 2H, J = 6.4 Hz), 3.97 (s, 3H), 1.29 (t, 3H, J = 6.0 Hz); 13C NMR (DMSO- d6): δ 158.2, 145.4, 135.3, 127.4, 62.2, 37.3, 14.5.

References

[1] Patent: WO2005/33077, 2005, A1. Location in patent: Page/Page column 53-54
[2] Journal of the American Chemical Society, 1996, vol. 118, # 26, p. 6141 - 6146
[3] Patent: US6090947, 2000, A

Ethyl 1-methyl-4-nitroimidazole-2-carboxylate(109012-23-9)Related Product Information

• Ethyl 1-methyl-4-nitroimidazole-2-carboxylate
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