13551-92-3

Usage

Chemical Properties

Yellow solid

InChI:InChI=1/C6H9N3O4/c10-4-5(11)3-8-2-1-7-6(8)9(12)13/h1-2,5,10-11H,3-4H2

Upstream product

• 527-73-1 2-nitro-1H-imidazole 
• 556-52-5 oxiranyl-methanol 
• 1262892-72-7 1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2-nitro-1H-imidazole 

Downstream Products

• 378230-70-7 toluene-4-sulfonic acid 2-hydroxy-3-(2-nitroimidazol-1-yl)propyl ester 

Relevant academic research and scientific papers

A new and improved synthesis of the precursor of the hypoxia marker [ 18F]-FMISO

A new synthetic approach to the precursor of the hypoxia marker [ 18F]-FMISO has been developed. Three different tosylation methods were studied for the preparation of the key intermediate. The overall yield is markedly higher than the yields reported for previous syntheses. The precursor was used to prepare [18F]-FMISO and the results were comparable to those obtained when a commercial precursor was used.

Facile and efficient synthesis of [18 F]Fluoromisonidazole using novel 2-nitroimidazole derivatives

[81F]Fluoromisonidazole ([ ([81F]FMISO) is a hypoxia imaging marker utilized in positron emission tomography. Novel FMISO precursors were prepared from a commercially available material, and several reaction factors that affect synthesis of [ [81F]FMISO were examined to achieve a higher fluorination yield. [18 F]FMISO was obtained from radiosynthesis, followed by the hydrolysis of protecting groups with HCl. New 2-nitroimidazole precursor showed a higher [18 F]fluorination and a higher synthetic yield. This result provided alternative guidelines for the preparation of hypoxia imaging marker.

Practical synthesis of 1-(2-Nitro-1H-imidazol-1-yl)-3-(tosyloxy) propan-2-yl acetate for the radiosynthesis of [18F]-FMISO

Hypoxia is related with many tumors due to a decreased oxygen condition. Novel synthesis for 1-(2-nitro-1H-imidazol-1-yl)-3-(tosyloxy)propan-2-yl acetate for the radiosynthesis of the [18F]-Flouromisonidazole ([18F]-FMISO), a hypoxia imaging marker used in positron emission tomography, from the readily available starting material is described. In this approach, one-pot two-step syntheses were used for the preparation of the [18F]-FMISO precursors that contain acetyl group. The mild reaction conditions and easy treatments are attractive features in this synthesis. This new synthetic route provides alternative choices for the preparation of hypoxia imaging marker.

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

The MRI hypoxia marker trifluoromisonidazole (TFMISO) [1-(2-nitro-1H- imidazol-1-yl)-3-(2,2,2-trifluoroethoxy)propan-2-ol] was successfully labeled with 18F to expand its role into a bimodal PET/MRI probe. 18F-Labeling was achieved via a three-step procedure in which 2,2,2-[18F]trifluoroethyl p-toluenesulfonate prepared by 18F-19F exchange served as the [18F] trifluoroethylating agent. The O-[18F]trifluoroethylation reaction proceeded efficiently to give the intermediate 1,2-epoxy-3-(2,2,2-[ 18F]trifluoroethoxy)propane, with approximately 60% of 18F incorporated from the tosylate precursor, which was condensed with 2-nitroimidazole to yield [18F]TFMISO. Approximately 40% of the [18F]trifluoroethyl tosylate precursor was converted into the final product. In stark contrast, 2,2,2-[18F]trifluoroethyl iodide failed to produce [18F]TFMISO, giving instead 1,1-[18F]difluoro- 2-iodoethoxy and 1-[18F]fluoro-2-iodovinyloxy analogs of [ 18F]TFMISO. Thus, this investigation has identified 2,2,2-[ 18F]trifluoroethyl tosylate as an excellent [18F] trifluoroethylating agent, which can convert efficiently an alcohol into the corresponding [18F]trifluoroethyl ether.