azidoacetic

Azidoacetic acid, also known as 2-azidoacetic acid or azidoethanoic acid, is an organic compound with the chemical formula N3CH2COOH. It is a derivative of acetic acid where one of the hydrogen atoms on the methyl group has been replaced by an azido group (N3). The azido group is a linear chain of three nitrogen atoms with a high-energy triple bond between the central and terminal nitrogen. This makes azidoacetic acid a potentially unstable and reactive compound, although it is generally more stable than many other organic azides.

Azidoacetic acid is typically a colorless liquid or low-melting solid. It exhibits acidic properties due to the presence of the carboxyl group. Its reactivity stems from both the azido group and the carboxyl group, allowing it to participate in various chemical transformations. The azido group can undergo reactions such as cycloadditions, reduction to an amine, or elimination of nitrogen gas. The carboxyl group can be esterified, amidated, or reduced. Due to its potential for energetic decomposition, azidoacetic acid should be handled with caution in a laboratory setting, employing appropriate safety precautions. It finds applications in organic synthesis as a building block for creating more complex molecules, particularly those containing nitrogen.