Methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate

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Methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate Basic information
Product Name:Methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate
Synonyms:Methyl 4-nitro-1-methylimidazole-2-carboxylate;Methyl -methyl-4-nitro-1H-imidazole-2-carboxylate;Methyl 1-Methyl-4-nitroimidazole-2-carboxylate;1H-Imidazole-2-carboxylic acid, 1-methyl-4-nitro-, methyl ester;3-BROMO-10-CHLOROPHENOL;Carbamicacid,N-[2-(2-bromoethoxy)ethyl]-,1,6-dimethylethylester;Methyl 1-methyl-4-nitro-1H-imidazol-2-carboxylate;Methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate
CAS:169770-25-6
MF:C6H7N3O4
MW:185.14
EINECS:
Product Categories:
Mol File:169770-25-6.mol
Methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate Structure
Methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate Chemical Properties
Melting point 157-158 °C
Boiling point 345.0±34.0 °C(Predicted)
density 1.49±0.1 g/cm3(Predicted)
storage temp. 2-8°C
pka-2.47±0.60(Predicted)
AppearanceWhite to off-white Solid
Safety Information
HazardClass IRRITANT
HS Code 2933299090
MSDS Information
Methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate Usage And Synthesis
Synthesis
Methanol

67-56-1

1-METHYL-4-NITRO-2-(TRICHLOROACETYL)-1H-IMIDAZOLE

120095-64-9

METHYL 1-METHYL-4-NITRO-1H-IMIDAZOLE-2-CARBOXYLATE

169770-25-6

The general procedure for the synthesis of methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate from methanol and 2,2,2-trichloro-1-(1-methyl-4-nitro-1H-imidazol-2-yl)ethanone was as follows: methanol (40 mL) was added to a reaction flask containing 2,2,2-trichloro-1-(1-methyl-4-nitro-1H-imidazol-2-yl)ethanone, heated to 40 °C and stirred for 10 minutes. Subsequently, a small amount of sodium hydride (100 mg) was added to the reaction mixture to ensure complete methanolysis. After continued stirring for 2 h, the reaction mixture was filtered to afford methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate in 94% yield. The product was confirmed by 1H-NMR (CDCl3): δ 7.84 (s, 1H, Im-CH), 4.18 (s, 3H, CH3), 3.93 (s, 3H, CH3).EI-HRMS analysis resulted in a m/z calculated value of 185.0437 for C6H7N3O4 and a measured value of 185.0476 (100%).

References[1] Patent: WO2007/45096, 2007, A1. Location in patent: Page/Page column 45; 86
[2] Heterocycles, 1995, vol. 41, # 6, p. 1181 - 1196
[3] Synthetic Communications, 2004, vol. 34, # 9, p. 1609 - 1615
Methyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate Preparation Products And Raw materials
Raw materialsMethanol-->1-Methyl-4-nitro-2-(trichloroacetyl)-1H-imidazole
Preparation ProductsMethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate
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