NNdiphenylurea3oxide

N,N-Diphenylurea 3-oxide, also referred to as diphenylcarbamoyl peroxide or diphenylcarbamoyl oxide, is an organic compound with the chemical formula C₁₃H₁₂N₂O₂. It belongs to the class of urea derivatives and is characterized by its unique structure, featuring a urea backbone with two phenyl groups attached to the nitrogen atoms and an additional oxygen atom bonded to the carbonyl carbon, forming a peroxide-like linkage.

This compound is primarily of interest in organic synthesis and materials science. It serves as a precursor in the preparation of various nitrogen-containing heterocycles and can act as a mild oxidizing agent in certain reactions. Its structure allows it to participate in rearrangements and cyclizations, making it useful in the synthesis of complex organic molecules.

N,N-Diphenylurea 3-oxide is typically prepared through the oxidation of N,N-diphenylurea using peracids, such as *m*-chloroperoxybenzoic acid (MCPBA). The reaction proceeds via electrophilic attack of the peracid on the urea carbonyl, leading to the formation of the peroxide intermediate.

Due to its sensitivity to heat and light, the compound is generally handled under controlled conditions to prevent decomposition. It is soluble in organic solvents like dichloromethane and acetone but sparingly soluble in water. While not widely commercialized, research into its applications continues, particularly in the development of pharmaceutical intermediates and specialty chemicals.

Safety considerations include its potential to act as a mild oxidizer, which may pose a fire hazard in combination with combustible materials. Proper storage in a cool, dry place away from strong oxidizers and reducing agents is recommended.