Fluoromisonidazole

Base Information

• Chemical Name: Fluoromisonidazole
• CAS No.: 13551-89-8
• Molecular Formula: C₆H₈FN₃O₃
• Molecular Weight: 189.146
• Hs Code.: 2933290090
• NSC Number: 292930
• UNII: 082285VIDF
• DSSTox Substance ID: DTXSID30875662
• Nikkaji Number: J965B
• Wikipedia: FMISO
• Wikidata: Q27236348
• ChEMBL ID: CHEMBL2068841
• Mol file: 13551-89-8.mol

Synonyms:(F-18) fluoromisonidazole;1-(2-nitro-1-imidazolyl)-3-fluoro-2-propanol;1-fluoro-2-hydroxypropyl-2-nitroimidazole;1-fluoromisonidazole;18F-fluoromisonidazole;18F-FMISO;fluoromisonidazole;fluoromisonidazole, 18F-labeled;fluoromisonidazole, tritium-labeled;fluoronormethoxymisonidazole;FMISO;Ro 07-0741

Chemical Property of Fluoromisonidazole

Chemical Property:

• Appearance/Colour: Yellow solid
• Vapor Pressure: 2.82E-08mmHg at 25°C
• Refractive Index: 1.589
• Boiling Point: 433.3 ºC at 760 mmHg
• Flash Point: 215.8 ºC
• PSA: 83.87000
• Density: 1.55 g/cm³
• LogP: 0.64490
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 189.05496929
• Heavy Atom Count: 13
• Complexity: 187

Purity/Quality:

99% ^*data from raw suppliers

1-FLUORO-3-(2-NITRO-1H-IMIDAZOL-1-YL)PROPAN-2-OL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=N1)[N+](=O)[O-])CC(CF)O
• Recent ClinicalTrials: A Phase II Trial of a Protease Inhibitor, Nelfinavir (NFV), Given With Definitive, Concurrent Chemoradiotherapy (CTRT) in Patients With Locally-Advanced, Human Papilloma Virus (HPV) Negative, Squamous Cell Carcinoma of the Head and Neck

Technology Process of Fluoromisonidazole

There total 11 articles about Fluoromisonidazole 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%

2-nitro-1H-imidazole (527-73-1) + 1-chloro-3-fluoroisopropanol (146580-24-7,453-11-2) → Fluoromisonidazole (13551-89-8)

Guidance literature:

2-nitro-1H-imidazole; With potassium tert-butylate; In N,N-dimethyl-formamide; at 130 ℃; for 0.25h;

1-chloro-3-fluoroisopropanol; With potassium iodide; In N,N-dimethyl-formamide; at 80 - 130 ℃; for 1h;

DOI:10.1016/j.jfluchem.2013.09.006

Reference yield: 78.0%

epifluorohydrine (503-09-3) + 2-nitro-1H-imidazole (527-73-1) → Fluoromisonidazole (13551-89-8)

Guidance literature:

With sodium hydrogencarbonate; In water; acetonitrile; at 100 ℃; for 1h;

DOI:10.1248/bpb.22.590

Reference yield: 55.0%

1-(3-fluoro-2-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-2-nitro-1H-imidazole → Fluoromisonidazole (13551-89-8)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; at 65 ℃; for 4h;

DOI:10.1016/j.ejmech.2015.06.023

upstream raw materials:

epifluorohydrine

2-nitro-1H-imidazole

1-chloro-3-fluoroisopropanol

2-nitro-1-(2-oxiranylmethyl)-1H-imidazole

Refernces

• 1、 Revunov, Evgeny,Zhuravlev, Fedor. "Co(salen)-mediated enantioselective radiofluorination of epoxides. Radiosynthesis of enantiomerically enriched [18F]F-MISO via kinetic resolution". . p. 130 - 135. Retrieved 2013.
• 2、 Borz?cka, Wioleta,Lavandera, Iván,Gotor, Vicente. "Biocatalyzed synthesis of both enantiopure fluoromisonidazole antipodes". supporting information. p. 5022 - 5025. Retrieved 2013/09/02.