tertButylnitrit

tert-Butyl nitrite is an organic nitrite with the formula (CH3)3C-ONO, commonly written as C4H9NO2. It is the tert-butyl ester of nitrous acid. The compound is a colorless to pale yellow volatile liquid at room temperature and has a characteristic fruity odor. As a nitrite ester, it acts as a nitrosating reagent in organic synthesis and can serve as a source of nitric oxide in biological contexts. It has historically been used as a vasodilator in inhalant mixtures, though such use raises safety concerns and is regulated in many jurisdictions; non-medical use is discouraged.

Preparation and handling: tert-Butyl nitrite is typically prepared by nitrosation of tert-butanol with nitrous acid generated in situ from sodium nitrite and an acid, conducted under anhydrous conditions to minimize hydrolysis. The compound is flammable and should be stored in tightly closed containers away from heat and oxidizers, in a well-ventilated area.

Safety: Inhalation can cause dizziness, headaches, and methemoglobinemia; skin and eye exposure can be irritating. It is reactive with strong bases and oxidizers and can form potentially hazardous decomposition products upon burning. Appropriate personal protective equipment and ventilation are required.

See also: Amyl nitrite and isopropyl nitrite, among other alkyl nitrites.