1-Ethyl-2-methyl-4-nitro-1H-imidazole

Base Information

• Chemical Name: 1-Ethyl-2-methyl-4-nitro-1H-imidazole
• CAS No.: 89128-07-4
• Molecular Formula: C₆H₉N₃O₂
• Molecular Weight: 155.156
• Hs Code.: 2933290090
• DSSTox Substance ID: DTXSID90350288
• Nikkaji Number: J603.549C
• Wikidata: Q82126148
• ChEMBL ID: CHEMBL1567311
• Mol file: 89128-07-4.mol

Synonyms:1-Ethyl-2-methyl-4-nitro-1H-imidazole;89128-07-4;1-ethyl-2-methyl-4-nitroimidazole;MLS000589579;Maybridge1_001955;CHEMBL1567311;HMS547A19;DTXSID90350288;HMS2581D09;BTB 09705;MFCD00156146;STK352058;AKOS001483159;SMR000212945;CS-0241133;EN300-231531;SR-01000389057;SR-01000389057-1

Chemical Property of 1-Ethyl-2-methyl-4-nitro-1H-imidazole

Chemical Property:

• PSA: 63.64000
• LogP: 1.64280
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 155.069476538
• Heavy Atom Count: 11
• Complexity: 156

Purity/Quality:

98%Min ^*data from raw suppliers

1-Ethyl-2-methyl-4-nitro-1H-imidazole 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1C=C(N=C1C)[N+](=O)[O-]

Technology Process of 1-Ethyl-2-methyl-4-nitro-1H-imidazole

There total 5 articles about 1-Ethyl-2-methyl-4-nitro-1H-imidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

ethyl bromide (74-96-4) + 2-methyl-4-nitro-1H-imidazole (696-23-1) → 1-ethyl-2-methyl-4-nitro-1H-imidazole (89128-07-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 110 - 120 ℃; for 3h;

DOI:10.1080/00397919108016766

Reference yield: 82.0%

ethyl bromide (74-96-4) + 2-methyl-5-nitro-1H-imidazole (696-23-1,88054-22-2) → 1-ethyl-2-methyl-4-nitro-1H-imidazole (89128-07-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 90 ℃; for 8h; Schlenk technique; Inert atmosphere;

DOI:10.1021/jo5025927

Reference yield:

ethyl bromide (74-96-4) + 2-methyl-5-nitro-1H-imidazole (696-23-1,88054-22-2) → 1-ethyl-2-methyl-4-nitro-1H-imidazole (89128-07-4) + 1-ethyl-2-methyl-5-nitro-1H-imidazole (41147-78-8)

Guidance literature:

With acetic acid; In N,N-dimethyl-formamide; at 80 - 140 ℃; for 10h; Product distribution; Mechanism; no temperature effects (80 - 140 deg C); regioselective alkylation (5-nitro-isomer);

upstream raw materials:

ethyl bromide

2-methyl-5-nitro-1H-imidazole

diethyl sulfate

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

Downstream raw materials:

1-Athyl-2-methyl-4-nitro-5-jodimidazol

Refernces

• 1、 Rao, A. K. S. Bhujanga,Rao, C. Gundu,Singh, B. B.. "Regioselective Alkylation of 4(5)-Nitro-1H-Imidazoles in Acidic Media: Study of Temperature Effects". . p. 2399 - 2402. Retrieved 2007/10/02.
• 2、 Bhujanga Rao,Gundu Rao,Sing. "A facile high yielding method for synthesis of N-alkyl-4-nitroimidazoles". . p. 427 - 433. Retrieved 2007/10/02.