Methyldiazonium Explained

Methyldiazonium is an organic compound consisting of a methyl group attached to a diazo group. This cation is the conjugate acid of diazomethane, with an estimated pKa<10.[1]

It is an intermediate in methylation reactions of diazomethane with acidic hydroxyl compounds, such as conversion of carboxylic acids to methyl esters and phenols to methyl ethers.[2]

It has been implicated as the metabolite of N-nitrosodimethylamine responsible for the observed carcinogenicity of that compound.[3]

Notes and References

  1. Fei. Na. Sauter. Basilius. Gillingham. Dennis. 2016. The pKa of Brønsted acids controls their reactivity with diazo compounds. Chemical Communications. en. 52. 47. 7501–7504. 10.1039/C6CC03561B. 27212133. free.
  2. Mechanism of Methyl Esterification of Carboxylic Acids by Trimethylsilyldiazomethane . Erik . Kühnel . David D. P. . Laffan . Guy C. . Lloyd-Jones . Teresa . Martínez del Campo . Ian R. . Shepperson . Jennifer L. . Slaughter . 10.1002/anie.200702131 . Angew. Chem. Int. Ed. Engl. . 46 . 37 . 2007 . 7075–7078 . 17691089 .
  3. 2017213 . Carcinogenic N-nitrosamines in the Diet: Occurrence, Formation, Mechanisms and Carcinogenic Potential . Mutation Research/Genetic Toxicology . 259 . 3–4 . 277–289 . 1991 . Tricker . A. R. . Preussmann . R. . 10.1016/0165-1218(91)90123-4 .

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