68019-78-3

Usage

Structure

An imidazole derivative with a methoxy group at the 4th position and a nitro group at the 5th position

Usage

Commonly used in organic synthesis and medicinal chemistry as a building block for the preparation of various pharmaceuticals and bioactive compounds

Relevance

Important for researchers and chemists working in the field of drug development and organic chemistry

Industrial application

Utilized in the chemical industry for the production of other valuable substances.

InChI:InChI=1/C4H5N3O3/c1-10-4-3(7(8)9)5-2-6-4/h2H,1H3,(H,5,6)

Upstream product

• 124-41-4 sodium methylate 
• 19183-14-3 4,5-dinitro-1H-imidazole 
• 76529-48-1 (4,5)-iodonitroimidazole 
• 67-56-1 methanol 
• 19182-81-1 1,4-dinitro-1H-imidazole 
• 6963-65-1 5-bromo-4-nitro-1H-imidazole 

Relevant academic research and scientific papers

Nucleophilic Displacements of Imidazoles.I. Oxygen,Nitrogen and Carbon Nucleophiles

4(5)-Bromo- and -iodo-imidazoles, activated by an adjacent nitro substituent, undergo nucleophilic displacement with methoxide, phenoxide, cyclic secondary amines and cyanide.The regiochemistry of the reactions of 5-iodo-4-nitroimidazole with methoxide has been confirmed by spectroscopic and X-ray methods, and a number of erroneous structures from the literature have been revised.Some apparently anomalous reactions of methoxide with 5-halo-1,2-dimethyl-4-nitroimidazoles, and of cyanide with 4-halo-1-methyl-5-nitroimidazole have been noted.The crystal and molecular structure of 5-methoxy-1-methyl-4-nitroimidazole has been determined by direct methods.Crystals are monoclinic, P21/c, a 10.929(3), b 8.899(2), c 7.290(2) Angstroem; β 92.87(2) deg; Z 4.The structure was refined to R=0.095 for 818 reflections (I.2?I).

REACTIONS OF 4,5-DINITROIMIDAZOLE AND 4(5)-NITROIMIDAZOLE-5(4)-SULFONIC ACID WITH NUCLEOPHILES

The reactions of 4,5-dinitroimidazole and 5(4)-nitroimidazole-4(5)-sulfonic acid with nucleophilic agents were studied.Mercapto-, alkoxy-, and aminonitroimidazoles were synthesized.In the reaction of dinitroimidazole with sodium alkoxides 5(4)-nitroimidazole was obtained in addition to alkoxynitroimidazoles.It is shown that in the formation of salts of the starting imidazoles with bases nucleophilic-substitution reactions take place only with "soft" reagents.