Diisopropylamine is a secondary amine with the chemical formula (Me2CH)2NH (Me = methyl). Diisopropylamine is a colorless liquid with an ammonia-like odor. Its lithium derivative, lithium diisopropylamide, known as LDA is a widely used reagent.

Reactions and use

Diisopropylamine is a common amine nucleophile in organic synthesis. Because it is bulky, it is a more selective nucleophile than other similar amines, such as dimethylamine. It reacts with organolithium reagents to give lithium diisopropylamide (LDA). LDA is a strong, non-nucleophilic base The main commercial applications of diisopropylamine is as a precursor to the herbicide, diallate and triallate as well as certain sulfenamides used in the vulcanization of rubber. It is also used to prepare N,N-diisopropylethylamine (Hünig's base) by alkylation with diethyl sulfate. The bromide salt of diisopropylamine, diisopropylammonium bromide, is a room-temperature organic ferroelectric material.

Preparation

Diisopropylamine, which is commercially available, may be prepared by the reductive amination of acetone with ammonia using a modified copper oxide, generally copper chromite, as a catalyst: Diisopropylamine can be dried by distillation from potassium hydroxide (KOH) or drying over sodium wire.

Toxicity

Diisopropylamine causes burns by all exposure routes. Inhalation of high concentrations of its vapor may cause symptoms like headache, dizziness, tiredness, nausea and vomiting.