Nitrosobenzene

Synthesis

Nitrosobenzene can be obtained by oxidation of aniline.

Aniline (2.043 g, 21.84 mmol) was added to a 250 mL round-bottom flask and dissolved in dichloromethane (50 mL). Potassium persulfate complex salt (27.378 g, 44.48 mmol) was dissolved in water (100 mL) and slowly added to the dichloromethane reaction solution. The reaction was stirred at room temperature, and the reaction solution gradually turned green. The reaction was monitored by TLC, and the reaction was stopped after 1 hour. The reaction solution was extracted with dichloromethane, and the dichloromethane phase was collected. The solvent was evaporated to dryness to obtain intermediate 4, i.e., Nitrosobenzene (green solid).

Chemical Properties

light yellow solid

Uses

Spin trap reagent. Has been used in the study of oxidative DNA damage and nitroso-compound-induced respiratory burst in neutrophils3,4.

Uses

Spin trap. Undergoes various addition, reduction, and oxidation reactions.

Definition

ChEBI: A nitroso compound that is the nitroso derivative of benzene; a diamagnetic hybrid of singlet O2 and azobenzene.

Purification Methods

Steam distil nitrosobenzene, then crystallise it from a small volume of EtOH with cooling below 0o, dry it over CaCl2 in a dessicator at atmospheric pressure, and store it under N2 at 0o. Alternatively it can be distilled onto a cold finger cooled with brine at ~-10o in a vacuum at 17mm (water pump), while heating in a water bath at 65-70o [Robertson & Vaughan J Chem Educ 27 605 1950]. [Beilstein 5 IV 702.]