What Is Diphenylamine?
Diphenylamine is an organic compound with the structural formula (C6H5)2NH. It is a secondary amine composed of two phenyl groups and is classified as an aromatic amine. Also known as N-phenylbenzeneamine or DPA, its CAS registration number is 122-39-4.
Uses of Diphenylamine
Diphenylamine serves various purposes, including as a reagent for detecting nitrates, a raw material for organic syntheses, and a stabilizer for explosives and chlorinated solvents. It’s notably used in the nitrate reaction for detecting nitrates and in DNA extraction.
As a synthetic raw material, it’s employed in pharmaceuticals, dyes, organic rubber chemicals, and phenothiazines, serving as a polymerization inhibitor. It’s also used in the synthesis of anti-aging agents and various dyes.
Properties of Diphenylamine
Diphenylamine, with a molecular formula C12H11N and molecular weight 169.23, is a white or yellow crystalline solid. It has a melting point of 53°C and a boiling point of 302°C. While insoluble in water, it readily dissolves in various organic solvents such as ethanol, acetone, benzene, and pyridine.
Types of Diphenylamine
Diphenylamine is sold as both an R&D reagent and an industrial chemical. Reagent-grade products come in various capacities and require refrigerated storage, while industrial-grade products are supplied in larger units for specific applications such as stabilizing dye intermediates and nitrocellulose.
Other Information on Diphenylamine
1. Synthesis of Diphenylamine
Diphenylamine is synthesized by pressurizing and heating aniline hydrochloride and aniline, or by the deamination reaction of aniline in the presence of an oxide catalyst.
2. Color Reaction of Diphenylamine
Diphenylamine undergoes color reactions such as the Runge test, turning dark blue in the presence of nitrate or nitrite ions, and the Dish reaction, producing a blue color with 2-deoxypentose. These reactions are used in detecting ions and DNA quantification, respectively.
3. Chemical Reaction of Diphenylamine
It reacts with strong acids to form salts and readily undergoes cyclization reactions, producing compounds like phenothiazine and carbazole.
4. Hazardousness of Diphenylamine
Diphenylamine is classified as hazardous due to potential serious effects on various systems and possible carcinogenicity. It should be handled with appropriate protective measures and in compliance with safety regulations.