1-(2-Hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole

Base Information

• Chemical Name: 1-(2-Hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole
• CAS No.: 4812-40-2
• Molecular Formula: C₆H₉N₃O₄
• Molecular Weight: 187.155
• Hs Code.: 29332900
• European Community (EC) Number: 641-568-5
• UNII: 7RUI9488IL
• DSSTox Substance ID: DTXSID20197426
• Nikkaji Number: J86.832I
• Wikipedia: Hydroxymetronidazole
• Wikidata: Q5955628
• Metabolomics Workbench ID: 87131
• ChEMBL ID: CHEMBL3544702
• Mol file: 4812-40-2.mol

Synonyms:1-(2-hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole;2-(hydroxymethyl)-5-nitro-1H-imidazole-1-ethanol;2-hydroxymethylmetronidazole;2-hydroxymetronidazole;20396 RP;RP 20396;RP-20396

Chemical Property of 1-(2-Hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole

Chemical Property:

• Vapor Pressure: 7.73E-10mmHg at 25°C
• Melting Point: 118-121°C
• Refractive Index: 1.5800 (estimate)
• Boiling Point: 475.2°Cat760mmHg
• PKA: 13.28±0.10(Predicted)
• Flash Point: 241.2°C
• PSA: 104.10000
• Density: 1.61g/cm³
• LogP: -0.20090
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Sparingly), Methanol (Slightly)
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 187.05930578
• Heavy Atom Count: 13
• Complexity: 183

Purity/Quality:

98%Min ^*data from raw suppliers

Hydroxy Metronidazole ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(N(C(=N1)CO)CCO)[N+](=O)[O-]
• Description: Hydroxy metronidazole is a metabolite of metronidazole. Metronidazole belongs to the nitroimidazole class of drugs. In agricultural production, it is often used as a drug to expel parasites in animals. After being added to animal feed, metronidazole remains in eggs. Because metronidazole has a variety of toxic and side effects on the human body, especially its potential carcinogenicity and hereditary mutation effects, and metronidazole can be rapidly distributed throughout the body after entering the human body, so the residual metronidazole and its metabolites in eggs inspection is necessary.
• Uses: Hydroxymetronidazole (Metronidazole-OH) is a metabolite of Metronidazole belonging to the class of nitroimidazoles. Hydroxymetronidazole can be used for the research of certain bacterial and protozoal diseases in poultry, swine dysentery and genital trichomoniasis in cattle.

Technology Process of 1-(2-Hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole

There total 6 articles about 1-(2-Hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole 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: 80.0%

methyl-(2-hydroxymethyl-5-nitro)imidazolylacetate (147124-51-4) → Hydroxymetronidazole (4812-40-2)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; for 0.25h; Ambient temperature;

DOI:10.1080/00397919308009770

Reference yield:

metronidazole (443-48-1) → 2-methyl-5-nitroimidazole-1-acetic acid (1010-93-1) + Metronidazole beta-D-glucuronide (100495-98-5) + Hydroxymetronidazole (4812-40-2)

Guidance literature:

rat liver slices; In water; at 37 ℃; Enzyme kinetics; Enzymatic reaction;

DOI:10.3109/00498259609046744

Reference yield:

(2-Hydroxymethyl-5-nitro-imidazol-1-yl)-acetic acid (147124-50-3) → Hydroxymetronidazole (4812-40-2)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol / 42 h / Ambient temperature

2: 80 percent / LiBH₄ / tetrahydrofuran / 0.25 h / Ambient temperature

With lithium borohydride; In tetrahydrofuran; methanol;

DOI:10.1080/00397919308009770

upstream raw materials:

methyl-(2-hydroxymethyl-5-nitro)imidazolylacetate

metronidazole

(2-Hydroxymethyl-5-nitro-imidazol-1-yl)-acetic acid

ethyl-(2-bromomethyl-5-nitro)imidazolylacetate

Refernces

• 1、 Hambalek,Just. "A facile synthesis of the major urinary metabolite of metronidazole". . p. 209 - 215. Retrieved 2007/10/02.