2-Nitrodiphenylamine

Description

2-Nitrodiphenylamine is a double-base (DB) rocket propellant stabilizer and its microencapsulation potentially improves the shelf life of DB rocket propellants.

Chemical Properties

Red Crystalline Solid

Uses

2-Nitrodiphenylamine is used to control the combustion of propylene glycol dinitrate in Otto fuel II (US navy propellant for torpedoes and other weapons systems); Also used as a solvent dye; Used as stabilizer for nitroglycerin and as a chemical intermediate

Uses

(2-Nitrophenyl)phenylamine (cas# 119-75-5) is a compound useful in organic synthesis.

General Description

Red-brown crystalline powder or reddish-brown solid.

Air & Water Reactions

2-Nitrodiphenylamine may be sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

2-Nitrodiphenylamine is incompatible with strong oxidizers, strong acids and strong bases.

Health Hazard

Symptoms of exposure to this chemical include irritation of the skin, eyes, mucous membranes and upper respiratory tract. Structurally similar chemicals may cause methemoglobinemia.  
ACUTE/CHRONIC HAZARDS: This chemical may be harmful by inhalation or ingestion. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides

Fire Hazard

Flash point data for 2-Nitrodiphenylamine are not available; however, 2-Nitrodiphenylamine is probably combustible.

Synthesis

The synthesis of 2-Nitrodiphenylamine is as follows:The mixture of phenylboronic acid (1 mmol), aromatic amine (1.2 mmol) and 0.12 g (2 mmol) of KF in DMSO (4 mL) were added to Cu-IS-AMBA-MNPs (0.06 g, 0.025 mmol) at 130 °C under nitrogen atmosphere for 2 h with vigorous stirring. Then, after completion of the reaction, the catalyst was separated by an external magnet and washed with dry CH2Cl2 three times and checked for its reusability. The solvent of the reaction mixture was evaporated by a rotary evaporator and then ethyl acetate and water were added to the residue. The organic layer was dried over anhydrous MgSO4. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography using ethyl acetate/n-hexane.