Tetramethylurea

Tetramethylurea (TMU) is an organic compound with the formula (CH3)4N2O. It is a colorless liquid, soluble in water and common organic solvents. Tetramethylurea is used as a solvent and as a reagent in organic synthesis.

Structure and Bonding[edit | edit source]

Tetramethylurea is a urea derivative and has a planar molecular geometry. The molecule is symmetric, with the nitrogen atoms forming a bridge between the two carbonyl groups. The carbonyl groups are in a trans configuration, which minimizes steric hindrance and allows for optimal overlap of the nitrogen's lone pair of electrons with the carbonyl group's antibonding orbital.

Synthesis[edit | edit source]

Tetramethylurea can be synthesized from dimethylamine and carbon dioxide. The reaction proceeds via the formation of a carbamate, which is then dehydrated to form the urea derivative.

Applications[edit | edit source]

Tetramethylurea is primarily used as a solvent in organic synthesis. It is particularly useful for reactions that require a polar, aprotic solvent. Additionally, it is used as a reagent in the synthesis of other organic compounds.

Safety[edit | edit source]

Like other urea derivatives, tetramethylurea is considered to be of low toxicity. However, it can cause irritation to the eyes and skin, and may be harmful if swallowed or inhaled.