Desmethylmisonidazole

Base Information

• Chemical Name: Desmethylmisonidazole
• CAS No.: 13551-92-3
• Molecular Formula: C6H9 N3 O4
• Molecular Weight: 187.155
• Hs Code.: 2933290090
• European Community (EC) Number: 236-932-1
• NSC Number: 261036
• UNII: H3N358OVQW
• DSSTox Substance ID: DTXSID50875669
• Nikkaji Number: J966K
• Wikidata: Q27279600
• NCI Thesaurus Code: C1065
• Mol file: 13551-92-3.mol

Synonyms:demethylmisonidazole;desmethylmisonidazole;Ro 05-9963

Chemical Property of Desmethylmisonidazole

Chemical Property:

• Vapor Pressure: 1.05E-11mmHg at 25°C
• Boiling Point: 521.5°Cat760mmHg
• Flash Point: 269.2°C
• PSA: 104.10000
• Density: 1.61g/cm³
• LogP: -0.33230
• Storage Temp.: 2-8°C
• XLogP3: -1
• 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:

99% ^*data from raw suppliers

3-(2-Nitro-1H-imidazol-1-yl)propane-1,2-diol 95+% ^*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(CO)O

Technology Process of Desmethylmisonidazole

There total 3 articles about Desmethylmisonidazole 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: 91.0%

1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2-nitro-1H-imidazole (1262892-72-7) → O-Desmethyl-misonidazole (13551-92-3)

Guidance literature:

With trifluoroacetic acid; In methanol; at 20 ℃; for 7h; Solvent; Reagent/catalyst; Temperature; Time;

DOI:10.1002/bkcs.10107

Reference yield: 45.0%

2-nitro-1H-imidazole (527-73-1) + oxiranyl-methanol (556-52-5) → O-Desmethyl-misonidazole (13551-92-3)

Guidance literature:

With potassium carbonate; In ethanol; for 0.666667h;

DOI:10.1016/j.bmc.2011.02.026

Reference yield:

→ O-Desmethyl-misonidazole (13551-92-3)

Guidance literature:

2-Nitro-imidazol + 1,2-Epoxy-3-hydroxy-propan.;

upstream raw materials:

1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2-nitro-1H-imidazole

2-nitro-1H-imidazole

oxiranyl-methanol

Downstream raw materials:

toluene-4-sulfonic acid 2-hydroxy-3-(2-nitroimidazol-1-yl)propyl ester

Refernces

• 1、 Kwon, Young-Do,Jung, Yongju,Lim, B Seok Tae,Sohna, Myung-Hee,Kim, Hee-Kwon. "Facile and efficient synthesis of [18 F]Fluoromisonidazole using novel 2-nitroimidazole derivatives". . p. 1150 - 1156. Retrieved 2016.
• 2、 Suehiro, Makiko,Yang, Guangbin,Torchon, Geralda,Ackerstaff, Ellen,Humm, John,Koutcher, Jason,Ouerfelli, Ouathek. "Radiosynthesis of the tumor hypoxia marker [18F]TFMISO via O-[18F]trifluoroethylation reveals a striking difference between trifluoroethyl tosylate and iodide in regiochemical reactivity toward oxygen nucleophiles". experimental part. p. 2287 - 2297. Retrieved 2011/05/12.