4-(5-Bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-2-butanone

Base Information

• Chemical Name: 4-(5-Bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-2-butanone
• CAS No.: 139975-79-4
• Molecular Formula: C8H10BrN3O3
• DSSTox Substance ID: DTXSID701199227
• Nikkaji Number: J476.480C
• Mol file: 139975-79-4.mol

Synonyms:DTXSID701199227;4-(5-Bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-2-butanone;139975-79-4

Chemical Property of 4-(5-Bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-2-butanone

Chemical Property:

• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 274.99055
• Heavy Atom Count: 15
• Complexity: 268

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=NC(=C(N1CCC(=O)C)Br)[N+](=O)[O-]

Technology Process of 4-(5-Bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-2-butanone

There total 3 articles about 4-(5-Bromo-2-methyl-4-nitro-1H-imidazol-1-yl)-2-butanone 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: 93.0%

3-(2-methyl-4-nitroimidazol-1-yl)-propionic acid methyl ester (16935-06-1) → methyl 3-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)propanoate (139975-79-4)

Guidance literature:

With bromine; potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 60 - 70 ℃; for 3h;

DOI:10.1021/jo00037a051

Reference yield: 55.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + 5-bromo-2-methyl-4-nitro-1H-imidazole (18874-52-7) → methyl 3-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)propanoate (139975-79-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 60 ℃; for 72h; regioselective reaction; Inert atmosphere;

DOI:10.3762/bjoc.7.24

Reference yield:

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + 5-bromo-2-methyl-4-nitro-1H-imidazole (18874-52-7) → methyl 3-(4-bromo-2-methyl-5-nitroimidazol-1-yl)propanoate (1273542-80-5) + methyl 3-(5-bromo-2-methyl-4-nitro-1H-imidazol-1-yl)propanoate (139975-79-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 60 ℃; for 96h; Inert atmosphere;

DOI:10.3762/bjoc.7.24

upstream raw materials:

3-(2-methyl-4-nitroimidazol-1-yl)-propionic acid methyl ester

acrylic acid methyl ester

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