2-Nitroimidazole

Base Information

• Chemical Name: 2-Nitroimidazole
• CAS No.: 527-73-1
• Deprecated CAS: 116421-32-0,151223-78-8,151223-78-8
• Molecular Formula: C3H3N3O2
• Molecular Weight: 113.076
• Hs Code.: 29332990
• European Community (EC) Number: 208-425-5
• NSC Number: 105831
• UNII: K8E96XL55D
• DSSTox Substance ID: DTXSID7060178
• Nikkaji Number: J3.641B
• Wikipedia: Nitroimidazole
• Wikidata: Q27135639
• Metabolomics Workbench ID: 64935
• ChEMBL ID: CHEMBL433637
• Mol file: 527-73-1.mol

Synonyms:azomycin;azomycin, monohydrofluoride;azomycin, sodium salt;Ro-59129-001

Chemical Property of 2-Nitroimidazole

Chemical Property:

• Appearance/Colour: pale yellow solid
• Vapor Pressure: 8.86E-06mmHg at 25°C
• Melting Point: 287 °C (dec.)(lit.)
• Refractive Index: 1.612
• Boiling Point: 373.6 °C at 760 mmHg
• PKA: 8.72±0.10(Predicted)
• Flash Point: 179.7 °C
• PSA: 74.50000
• Density: 1.552 g/cm³
• LogP: 0.84110
• Storage Temp.: Refrigerator
• Solubility.: NH4OH: soluble50mg/mL, clear, yellow to orange
• Water Solubility.: insoluble
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 113.022526347
• Heavy Atom Count: 8
• Complexity: 99.2

Purity/Quality:

99% ^*data from raw suppliers

2-Nitroimidazole >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T
• Statements: 22-36/37/38-23/24/25-20/21/22
• Safety Statements: 26-36-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN=C(N1)[N+](=O)[O-]
• Uses: 2-Nitroimidazole is a antibiotic substance produced by an unidentified Streptomyces,it is used to prepare nitroimidazole substituted boronic acids as precursors for imaging hypoxic tissue 1.It is also used to prepare potential site-selective radiosensitizers for estrogen receptor-rich tumors. 2-Nitroimidazole, is used as an antibiotic in pharma industry. Antibiotic substance produced by an unidentified Streptomyces

Technology Process of 2-Nitroimidazole

There total 6 articles about 2-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: 69.8%

2-bromo-1H-imidazole (16681-56-4,151223-74-4) → 2-nitro-1H-imidazole (527-73-1)

Guidance literature:

With copper(l) iodide; sodium nitrite; In dimethyl sulfoxide; at 150 ℃; for 3h; Temperature; Solvent;

Reference yield: 68.0%

2-aminoimidazole hemisulfate → 2-nitro-1H-imidazole (527-73-1)

Guidance literature:

2-aminoimidazole hemisulfate; With sodium nitrate; sulfuric acid; In water; at 0 ℃; for 0.5h;

With copper(ll) sulfate pentahydrate; sodium hydrogencarbonate; sodium nitrite; In water; at 50 ℃; for 2h;

Reference yield: 67.0%

1H-imidazol-2-amine (7720-39-0) → 2-nitro-1H-imidazole (527-73-1)

Guidance literature:

With oxone||potassium monopersulfate triple salt; In water; at 40 ℃; for 18h; Green chemistry;

DOI:10.1021/op5000754

upstream raw materials:

1H-imidazol-2-amine

N-tritylimidazole

2-aminoimidazolesulfate

2-bromo-1H-imidazole

Downstream raw materials:

4-Morpholinomethyl-2-nitro-imidazol

1-(2-hydroxy-3-buten-1-yl)-2-nitroimidazole

1-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2-nitroimidazole

1-(2,3,5-tri-O-benzoyl-β-D-arabinofuranosyl)-2-nitroimidazole

Refernces

• 1、 Assun??o, Elvis L. F.,Carvalho, Diego B.,das Neves, Amarith R.,Kawasoko Shiguemotto, Cristiane Y.,Portapilla, Gisele B.,de Albuquerque, Sergio,Baroni, Adriano C. M.. "Synthesis and Antitrypanosomal Activity of 1,4-Disubstituted Triazole Compounds Based on a 2-Nitroimidazole Scaffold: a Structure-Activity Relationship Study". . p. 2019 - 2028. Retrieved 2020/09/21.
• 2、 Kennedy, David C.,James, Brian R.. "Synthesis and antiproliferatory activity of ruthenium complexes containing N-heterocyclic carboxylates". . p. 32 - 36. Retrieved 2017/03/11.