Tert-Butyl nitrite

Tert-Butyl nitrite (TBN) is an organic compound with the molecular formula C4H9NO2. It is a colorless liquid that is used as a reagent in organic synthesis. TBN is a nitrite ester, a type of ester that is derived from nitrous acid and an alcohol.

History

Tert-Butyl nitrite was first synthesized in the late 19th century. The compound was initially used in the production of dyes and pigments, but its use has since expanded to include a variety of applications in organic synthesis.

Properties

TBN is a colorless liquid at room temperature. It has a boiling point of 67-68 °C and a density of 0.96 g/mL. The compound is soluble in most organic solvents, but is less soluble in water.

Synthesis

Tert-Butyl nitrite can be synthesized by reacting tert-butanol with sodium nitrite in the presence of sulfuric acid. The reaction proceeds via the formation of a nitrosyl ion, which then reacts with the alcohol to form the nitrite ester.

Applications

TBN is used as a reagent in organic synthesis. It is particularly useful for the nitrosation of amines, a reaction that forms nitroso compounds. TBN can also be used to introduce a nitro group into an organic molecule, a process known as nitration.

Safety

TBN is a flammable liquid and should be handled with care. It can cause burns and eye damage, and may be harmful if inhaled. Appropriate safety measures should be taken when handling this compound.

See also

• Nitrite
• Organic synthesis
• Nitrosation
• Nitration