Methyl 3-methyl-2-nitro-3H-imidazole-4-carboxylate

Base Information

• Chemical Name: Methyl 3-methyl-2-nitro-3H-imidazole-4-carboxylate
• CAS No.: 40361-79-3
• Molecular Formula: C6H7N3O4
• Molecular Weight: 185.139
• Hs Code.: 2933290090
• NSC Number: 307220
• DSSTox Substance ID: DTXSID40878902
• Nikkaji Number: J1.561.305J
• Wikidata: Q82860921
• ChEMBL ID: CHEMBL3247251
• Mol file: 40361-79-3.mol

Synonyms:40361-79-3;METHYL 3-METHYL-2-NITRO-3H-IMIDAZOLE-4-CARBOXYLATE;3-Methyl-2-nitro-3H-imidazole-4-carboxylic acid methyl ester;methyl 3-methyl-2-nitroimidazole-4-carboxylate;METHYL 1-METHYL-2-NITRO-1H-IMIDAZOLE-5-CARBOXYLATE;1H-Imidazole-5-carboxylic acid, 1-methyl-2-nitro, methyl ester;NSC307220;CHEMBL3247251;DTXSID40878902;MFCD06738745;AKOS006293393;AB27794;NSC 307220;NSC-307220;AS-30828;1-ME-2-NO2-5-MEOCARBONYL IMIDAZOLE;CS-0199781;FT-0649310;methyl 3-methyl-2-nitro-imidazole-4-carboxylate;A825071;3-methyl-2-nitro-4-imidazolecarboxylic acid methyl ester;METHYL3-METHYL-2-NITRO-3H-IMIDAZOLE-4-CARBOXYLATE;1-METHYL-2-NITRO-1H-IMIDAZOLE-5-CARBOXYLIC ACID METHYL ESTER

Chemical Property of Methyl 3-methyl-2-nitro-3H-imidazole-4-carboxylate

Chemical Property:

• Vapor Pressure: 8.23E-06mmHg at 25°C
• Boiling Point: 374.6°C at 760 mmHg
• Flash Point: 180.4°C
• PSA: 89.94000
• Density: 1.49g/cm³
• LogP: 0.63810
• Storage Temp.: 2-8°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 185.04365571
• Heavy Atom Count: 13
• Complexity: 226

Purity/Quality:

98%min ^*data from raw suppliers

Methyl3-Methyl-2-nitro-3H-imidazole-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=CN=C1[N+](=O)[O-])C(=O)OC

Technology Process of Methyl 3-methyl-2-nitro-3H-imidazole-4-carboxylate

There total 3 articles about Methyl 3-methyl-2-nitro-3H-imidazole-4-carboxylate 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: 58.0%

2-amino-1-methyl-1H-imidazole-5-carboxylic acid methyl ester (40361-77-1) → 1-methyl-2-nitro-1H-imidazole-5-carboxylic acid methyl ester (40361-79-3)

Guidance literature:

With acetic acid; NaNO₂; In water monomer; at 20 ℃; for 23h; Cooling with ice;

DOI:10.1002/cmdc.201600417

Reference yield:

2-(formyl-methyl-amino)-3-oxo-propionic acid methyl ester (40361-84-0) → 1-methyl-2-nitro-1H-imidazole-5-carboxylic acid methyl ester (40361-79-3)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; sodium acetate / 3 h / 100 °C

2: acetic acid; sodium nitrite / water / 23 h / 20 °C / Cooling with ice

With sodium acetate; acetic acid; sodium nitrite; In water;

DOI:10.1002/cmdc.201600417

Reference yield:

→ 1-methyl-2-nitro-1H-imidazole-5-carboxylic acid methyl ester (40361-79-3)

Guidance literature:

Amin (10), HNO2;

DOI:10.1021/jm00280a030

upstream raw materials:

2-(formyl-methyl-amino)-3-oxo-propionic acid methyl ester

2-amino-1-methyl-1H-imidazole-5-carboxylic acid methyl ester

Downstream raw materials:

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

1-methyl-2-nitro-5-hydroxymethylimidazole

Refernces

• 1、 -. "Preparation method of evofosfamide". Paragraph 0039; 0046-0049. . Retrieved 2020/02/20.
• 2、 Asato,Berkelhammer. "Nitroheterocyclic antimicrobial agents. 1-Methyl-2-nitro-5-imidazolyl derivatives.". . p. 1086 - 1088. Retrieved 2007/10/08.