Carbonyldiimidazole

CDI can also be used for esterification, although alcoholysis requires heat or the presence of a potent nucleophiles as sodium ethoxide,[1][3] or other strong bases like NaH.

The equilibrium can be shifted in the favor of the anhydride by utilizing an acid in a 2:1 ratio that forms an insoluble salt with the imidazole.

This reagent is a good formylating agent and can regenerate the unsubstituted imidazole (with formation of carbon monoxide) upon heating.

[1] A C-C acylation reaction can occur with a malonic ester-type compound, in the following scheme useful for syntheses of macrolide antibiotics.

[1] CDI can act as a carbonyl equivalent in the formation of tetronic acids or pulvinones from hydroxyketones and diketones in basic conditions.

[3] As CDI is an equivalent of phosgene, it can be used in similar reaction, however, with increased selectivity: it allows the synthesis of asymmetric bis alkyl carbonates[10] The safety characteristics of CDI have been investigated as part of a broader evaluation of amide bond forming reagents.

[11] The sensitization potential of CDI was shown to be low compared to other common amide bond forming agents (non-sensitizing at 1% in LLNA testing according to OECD 429[12]).

Thermal hazard analysis by differential scanning calorimetry (DSC) shows CDI poses minimal explosion risks.