3034-41-1

Usage

Uses

Used in Pharmaceutical Industry:
Imidazole, 1-methyl-4-nitrois used as a key moiety in the development of Azathioprine (A803350), an immunosuppressive drug. Imidazole, 1-methyl-4-nitrocontributes to the drug's effectiveness in suppressing the immune system, making it useful for treating various autoimmune diseases and preventing organ transplant rejection.
Additionally, due to its mutagenic potential, Imidazole, 1-methyl-4-nitromay also be utilized in research and development for understanding the effects of mutagens on biological systems and potentially developing new therapeutic strategies.

InChI:InChI=1/C4H5N3O2/c1-6-2-4(5-3-6)7(8)9/h2-3H,1H3

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 553-90-2 Dimethyl oxalate 
• 3034-38-6 1H-4⁽⁵⁾-nitroimidazole 
• 212248-40-3 1-Chloro-4-nitroimidazole 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 

Downstream Products

• 3034-43-3 1,3-dimethyl-4-nitroimidazolium iodide 
• 116271-00-2 1-methyl-4-nitro-5-phenylsulfonylmethylimidazole 
• 79578-98-6 1-methyl-1H-imidazol-4-amine 
• 4531-54-8 1-methyl-4-nitro-1H-imidazol-5-amine 
• 7464-68-8 1,5-dimethyl-4-nitro-1H-imidazole 
• 20041-97-8 2-(1-methyl-4-nitro-1H-imidazol-5-yl)acetic acid 
• 89088-69-7 1-methyl-1H-imidazole-4-amine hydrochloride 
• 1362909-87-2 (4-fluorophenyl)(4-(1-methyl-1H-imidazol-4-ylamino)quinazolin-2-yl)methanone 
• 1208893-80-4 2,6-dichloro-N-(1-methyl-1H-imidazol-4-yl)pyrimidin-4-amine 
• 107-97-1 sarcosine 
• 7664-41-7 ammonia 
• 74-89-5 methylamine 

Relevant academic research and scientific papers

Molten-state nitration of substituted imidazoles: New synthetic approaches to the novel melt-cast energetic material, 1-methyl-2,4,5-trinitroimidazole

Novel, one-step synthetic routes for the preparation of 1-methyl-2,4,5-trinitroimidazole (MTNI) are described. In addition, a new, molten-state nitration method for the synthesis of 1-methyl-2,4,5- trinitroimidazole is developed. Georg Thieme Verlag Stuttgart - New York.

Melt-cast explosive material

1-Methyl-2,4,5-Trinitroimidazole is synthesized starting from 4-nitroimidazole using stepwise nitration method and further methylation using Dimethylsulphate. It is relatively insensitive to impact and its thermal stability is excellent. The calculated detonation properties indicate that its performance is about 30% better than TATB. It can be prepared easily, with reasonable yield, starting from commercially available Imidazole. Results from impact sensitivity, friction sensitivity, time-to-explosion temperature and vacuum stability tests indicate that it is less sensitive than both RDX and HMX. The good oxygen balance and measured heat of formation data of this material indicate that its propellant performance should be good.

Oxidative Alkylation of Azoles: V. Synthesis of 1-Chloro-4-nitroimidazole and Its Reaction with Methyl Iodide

Chlorination of 4-nitroimidazole in alkaline medium gave 1-chloro-4-nitroimidazole. The reaction of the latter with methyl iodide results in liberation of iodine and formation of 4-nitroimidazole, isomeric 1-methyl-4-nitro- and 1-methyl-5-nitroimidazoles, and 1,3-dimethyl-4-nitroimidazolium triiodide.

Reactions with Dimethyl Carbonate, 2. - N-Methylation of Imidazole and Derivatives

The use of dimethyl carbonate as methylating agent for imidazole derivatives is demonstrated by selected examples.The comparison of the toxicological values of dimethyl carbonate and dimethyl sulfate should inspire to replace the highly toxic dimethyl sulfate by dimethyl carbonate.

A NEW SIMPLE PROCEDURE FOR ALKYLATION OF NITROGEN HETEROCYCLES USING DIALKYL OXALATES AND ALKOXIDES.

A variety of nitrogen heterocycles are N-alkylated in high yields with dialkyl oxalates and potassium alkoxides in refluxing dimethylformamide.