Diisopropylamine

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Diisopropylamine

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Template:Longitem	605284
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UN number	1158
Template:Longitem	Template:Chembox Elements/molecular formula
Molar mass	Template:Chem molar mass
Appearance	Colorless liquid
Odor	Fishy, ammoniacal
Density	0.722 g mL−1
Melting point	Template:Chembox CalcTemperatures
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Vapor pressure	9.3 kPa (at 20°C)
Acidity (pKa)	11.07 (in water) (conjugate acid)
Basicity (pKb)	3.43
Template:Longitem	1.392–1.393
Template:Longitem	−173.6 to −168.4 kJ mol−1
Template:Longitem	−4.3363 to −4.3313 MJ mol−1
NFPA 704 (fire diamond)	Template:NFPA 704 diamond
Flash point	Template:Chembox CalcTemperatures
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Explosive limits	1.1–7.1%
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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:

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Diisopropylamine can be dried by distillation from potassium hydroxide (Template:Chem2) or drying over sodium wire.Template:Rp

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.