tBuONO

tBuONO, short for tert-butyl nitrite, is an alkyl nitrite with the chemical formula C4H9NO2. It consists of a tert-butyl group bonded to an -ONO nitrite moiety. In organic synthesis it is used as a mild nitrosating agent capable of transferring a nitroso group to amines and related substrates, often under acidic conditions that generate nitrosonium species in situ. Because of this reactivity, tert-butyl nitrite is commonly employed to prepare N-nitrosamines from amines.

Preparation and handling methods are typically described in the context of organic synthesis. A common laboratory route involves the nitrosylation of tert-butanol with nitrosyl chloride (NOCl) to give tert-butyl nitrite and hydrogen chloride as a byproduct. It is a volatile, flammable liquid with a characteristic odor and is usually handled under appropriate fume-hood conditions and away from oxidizers or sources of ignition.

Physical properties are consistent with many alkyl nitrites: relatively low boiling point and high volatility, good solubility in organic solvents, and compatibility with nonaqueous media. As with other nitrites, tert-butyl nitrite can release nitric oxide (NO) under certain conditions, contributing to vasodilatory effects if encountered in consumer contexts.

Safety and toxicity considerations are important. Exposure can irritate the eyes, skin, and respiratory tract. Ingestion or inhalation of vapors can cause headaches, dizziness, and hypotension. It should be stored in tightly closed containers, away from heat, light, and incompatible substances, and used with proper protective equipment in well-ventilated facilities.

In addition to laboratory use, alkyl nitrites have historical and contemporary roles as vasodilators in consumer products, though tert-butyl nitrite is primarily encountered in research settings as a reactive nitrosating agent.

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