Issue 12, 2022

Rapid ‘on-column’ preparation of hydrogen [11C]cyanide from [11C]methyl iodide via [11C]formaldehyde

Abstract

Hydrogen [11C]cyanide ([11C]HCN) is a versatile 11C-labelling agent for the production of 11C-labelled compounds used for positron emission tomography (PET). However, the traditional method for [11C]HCN production requires a dedicated infrastructure, limiting accessibility to [11C]HCN. Herein, we report a simple and efficient [11C]HCN production method that can be easily implemented in 11C production facilities. The immediate production of [11C]HCN was achieved by passing gaseous [11C]methyl iodide ([11C]CH3I) through a small two-layered reaction column. The first layer contained an N-oxide and a sulfoxide for conversion of [11C]CH3I to [11C]formaldehyde ([11C]CH2O). The [11C]CH2O produced was subsequently converted to [11C]HCN in a second layer containing hydroxylamine-O-sulfonic acid. The yield of [11C]HCN produced by the current method was comparable to that of [11C]HCN produced by the traditional method. The use of oxymatrine and diphenyl sulfoxide for [11C]CH2O production prevented deterioration of the molar activity of [11C]HCN. Using this method, compounds labelled with [11C]HCN are now made easily accessible for PET synthesis applications using readily available labware, without the need for the ‘traditional’ dedicated cyanide synthesis infrastructure.

Graphical abstract: Rapid ‘on-column’ preparation of hydrogen [11C]cyanide from [11C]methyl iodide via [11C]formaldehyde

Supplementary files

Article information

Article type
Edge Article
Submitted
17 Dec 2021
Accepted
01 Mar 2022
First published
08 Mar 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 3556-3562

Rapid ‘on-column’ preparation of hydrogen [11C]cyanide from [11C]methyl iodide via [11C]formaldehyde

T. Kikuchi, M. Ogawa, T. Okamura, A. D. Gee and M. Zhang, Chem. Sci., 2022, 13, 3556 DOI: 10.1039/D1SC07033A

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