2-(2-Methyl-4-nitro-1H-imidazol-1-yl)ethanol

Base Information

• Chemical Name: 2-(2-Methyl-4-nitro-1H-imidazol-1-yl)ethanol
• CAS No.: 705-19-1
• Molecular Formula: C6H9N3O3
• Molecular Weight: 171.15396
• UNII: 0WI2PRW4QM
• DSSTox Substance ID: DTXSID00220766
• Nikkaji Number: J848F
• Wikidata: Q27231189
• ChEMBL ID: CHEMBL506657
• Mol file: 705-19-1.mol

Synonyms:1-(2'-hydroxyethyl)-2-methyl-4-nitroimidazole;iso-metronidazole;isometronidazole;isometronidazole monohydrochloride

Chemical Property of 2-(2-Methyl-4-nitro-1H-imidazol-1-yl)ethanol

Chemical Property:

• Melting Point: 140 °C
• Boiling Point: 405.4 °C at 760 mmHg
• PKA: 14.44±0.10(Predicted)
• Flash Point: 199 °C
• PSA: 83.87000
• Density: 1.45 g/cm³
• LogP: 0.61520
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 171.06439116
• Heavy Atom Count: 12
• Complexity: 170

Purity/Quality:

99%, ^*data from raw suppliers

Isometronidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC(=CN1CCO)[N+](=O)[O-]
• Uses: Isometronidazole (Metronidazole EP Impurity E) is an impurity of Metronidazole (M338880), a chemotherapeutic agent that is used as a first line defense against Clostridium difficile (C.diff). Isometronidazole is also a hypoxic cell sensitizer in humans and mice.

Technology Process of 2-(2-Methyl-4-nitro-1H-imidazol-1-yl)ethanol

There total 3 articles about 2-(2-Methyl-4-nitro-1H-imidazol-1-yl)ethanol 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: 94.0%

2-methyl-4-nitro-1H-imidazole (696-23-1) + 2-chloro-ethanol (107-07-3) → 1-(2-hydroxyethyl)-2-methyl-4-nitro-1H-imidazole (705-19-1)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; at 70 - 80 ℃; for 2h;

DOI:10.1080/00397919308012596

Reference yield: 81.0%

2-methyl-4-nitro-1H-imidazole (696-23-1) + 2-bromoethanol (540-51-2) → 1-(2-hydroxyethyl)-2-methyl-4-nitro-1H-imidazole (705-19-1)

Guidance literature:

With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/acs.cgd.1c00659

Reference yield:

→ 1-(2-hydroxyethyl)-2-methyl-4-nitro-1H-imidazole (705-19-1)

Guidance literature:

entspr. Acetat, HCl / W.;

upstream raw materials:

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

2-chloro-ethanol

2-bromoethanol

Downstream raw materials:

3-(2-methyl-4-nitro-imidazol-1-yl)propionitrile

1-(2-(4-(trifluoromethoxy)benzyloxy)ethyl)-2-methyl-4-nitro-1H-imidazole

1,3-dimethyl-7-(2-(2-methyl-4-nitro-1H-imidazol-1-yl)ethyl)-1H-purine-2,6(3H,7H)-dione

1-(2-(2-methyl-4-nitro-1H-imidazol-1-yl)ethyl)-1H-benzo[d]imidazole

Refernces

• 1、 Kim, Pilho,Zhang, Liang,Manjunatha, Ujjini H.,Singh, Ramandeep,Patel, Sejal,Jiricek, Jan,Keller, Thomas H.,Boshoff, Helena I.,Barry III, Clifton E.,Dowd, Cynthia S.. "Structure-activity relationships of antitubercular nitroimidazoles. 1. structural features associated with aerobic and anaerobic activities of 4 - And 5-nitroimidazoles". experimental part. p. 1317 - 1328. Retrieved 2009/12/07.