NNNNtetramethylurea

NNNNtetramethylurea is a substituted urea in which both nitrogens carry two methyl groups. Also called N,N,N',N'-tetramethylurea or tetramethylurea, its molecular formula is C5H12N2O, and its structure is a carbonyl group (O=C) bonded to two N,N-dimethyl groups (O=C(NMe2)2).

Synthesis of NNNNtetramethylurea typically proceeds by exhaustive methylation of urea using methylating reagents such as methyl iodide or dimethyl sulfate in the presence of a base, followed by purification, often by distillation. The procedure yields a stable, high-boiling amide that can be isolated as a colorless liquid.

As a solvent, NNNNtetramethylurea is valued for its high polarity and relatively high boiling point, which confer strong solvating ability while remaining a nonvolatile medium. It is miscible with water and with many organic solvents, and it is used as a polar aprotic solvent in organic synthesis, including reactions that require a highly polar, non-nucleophilic environment. It has also been employed as a precursor for the preparation of other urea derivatives and in studies of solvent effects on reaction mechanisms.

Safety and handling of NNNNtetramethylurea follow standard laboratory practices for amide solvents. Use appropriate personal protective equipment, work in a ventilated area, and dispose of waste according to institutional guidelines. Further information is available from the material safety data sheet and chemical suppliers.